Events in Key West
Trivia Tuesday at Mary Ellen's
Participants can put their knowledge to the test in a lively trivia session with chances to win fun prizes. After the final round, $8 Draft Cocktails are available.
Spider-Man: Brand New Day
A forgotten Peter Parker lives in solitude, serving as Spider-Man full time, until rising pressure sparks a dangerous change and a powerful new enemy appears. Rated PG-13, with a runtime of 2 hours and 25 minutes.
Euchre with the Brewer.
A friendly euchre game welcomes beginners and seasoned players alike. No experience is required, and instruction is provided so newcomers can learn as they play.
28th Annual Key West Lobsterfest
Marking its 28th year, Key West Lobsterfest honors the beloved crustacean with poolside parties, bar crawls, an outdoor street event, and a no-cost concert. Throughout the celebration there is plenty of fresh lobster to enjoy.
Duval StreetLobsterfest Trivia Night
Bring your best brainpower to a relaxed, lobster-themed trivia night on the Dewey Deck at Southernmost Beach Resort. Teams of up to six will work through five rounds of questions, competing for prizes and the ultimate bragging rights as the island’s top trivia team. Tickets are $50 per person and include one lobster roll and a drink. Capacity is limited to 50 participants. Plan to arrive early so your team can settle in, and be ready to think fast or make a clever guess.
Dewey Deck at Southernmost Beach ResortLobsterfest Kick-Off Party
This celebration began with a contest for the island’s best lobster dish. It kicks off the 28th Annual Key West Lobsterfest as freezers are cleared to make room for freshly caught lobster. Attendees can find lobster pizza and drink specials featuring official sponsors Sun Cruiser Iced Tea and Cuervo 1800 Tequila.
Rick's & Durty Harrys' Entertainment ComplexBusiness Before Hours
Connect with business leaders from Key West and nearby communities at a casual networking event held at the Greater Key West Chamber of Commerce. Everyone is welcome to attend, and Chamber membership is not required. Those considering membership can use this opportunity to learn more and meet local professionals. The event is supported by First State Bank.
Greater Key West Chamber of CommerceRockHouse
Experience seven consecutive nights of high-octane rock at Sloppy Joe’s in Key West, Florida. Nonstop energy meets a tropical backdrop for a full week of live music.
Sloppy Joe'sCarson Lowe on Wednesday, Aug 5, 2026
Carson Lowe is performing live at Rick's Bar in Key West. This daytime set runs from late morning into the afternoon.
Rick's BarA Pirate Looks Back: Jimmy Buffett Tribute Show
Enjoy a Jimmy Buffett tribute performed by A Pirate Looks Back. Expect music and a relaxed island vibe as the show celebrates the sounds of Buffett.
Comedy Key West🧘♂️Meditation With Alan 🧘🏻♂️
Step away from the week’s rush for a calm meditation session with Alan in the MCC Key West Sanctuary. Held every Thursday, this quiet gathering offers space to breathe, reset, and cultivate steadiness.
MCC Key West🧘 Meditation with Allen 🧘
Meditation with Allen offers a peaceful pause during the week, creating a quiet space for reflection, grounding, and renewal. All are welcome. Participants can come as they are, settle in, and focus on their breath.
MCC Key WestFlight of the Flamingos
An exclusive collaboration from Richard Blais Kitchen brings the Four Flamingos teams from Key West and Orlando together for a one-night culinary celebration of Florida’s lobster season. The experience features Celebrity Chef Richard Blais, Executive Chef Leo Minelli of Four Flamingos Key West, and Executive Chef Josue Perez of Four Flamingos Orlando, uniting two destinations in a multi-course menu that highlights their distinctive flavors and traditions. For the amuse bouche, choose either a Key West short rib croqueta with braised short rib, Argentinian chimichurri, pickled shallots and a micro arugula salad, or an Orlando passion fruit tuna ceviche made with seasonal fresh fish, a coconut and passion fruit leche de tigre, and pickled Fresno chiles. The first course offers a Key West yellowfin tuna tostada on a crisp corn base with avocado tartare and a silky mango yolk, or an Orlando crispy pork belly with pineapple rum glaze, jalapeño chimichurri, gochujang aioli, pickled pineapple and Fresno peppers. For the main course, select a Key West pairing of spiny lobster tail and black grouper with garlic drawn butter, avocado mousse, fresh chopped salad and coconut rice, or an Orlando duet of spiny lobster tail and center cut filet with Florida Gouda mash, sauce au poivre and wild mushrooms. Dessert concludes with a choice of award winning Key West key lime pie with raspberry gelée and flambéed meringue, or an Orlando coconut panna cotta served with fresh mango tartare. Price is $110 per person, plus tax and gratuity.
Four Flamingos, A Richard Blais Key West KitchenOne Piece TCG - Thursday Night League
Take part in a weekly One Piece TCG tournament that welcomes players eager to test their decks and enjoy friendly competition. Participants receive promo packs, and the player with the best record earns an exclusive winner pack.
Key West CollectiblesLobster Boil
Celebrate the opening of Florida’s spiny lobster season with a traditional boil set in the historic Porter Mansion’s tropical courtyard. Serving as the opening meal for the 28th Annual Key West Lobsterfest, this limited-capacity gathering blends island history, live music, and a full bar with a hearty seafood spread served hot with plenty of melted butter. Expect fresh Florida spiny lobsters (sweet, tender, and known for tail meat rather than claws), smoky red skin potatoes, corn on the cob, and warm jalapeño cornbread. The atmosphere leans toward casual island elegance with live local tunes and chilled drinks featuring festival sponsors Sun Cruiser Iced Tea and Cuervo 1800 Tequila. Hosted in the Porter Mansion courtyard at Caroline’s Cafe in Historic Old Town, the intimate setting often sells out early.
Porter MansionPokémon League
Connect with other fans of the Pokémon Trading Card Game at a Pokémon League to play and trade. Bring your own cards, take part in matches, and work toward earning prizes alongside players who enjoy collecting and playing just as much as you do.
Key West CollectiblesTaking Back Thursday's!
At 22&Co with Joe, this throwback party channels the spirit of 2001. Expect a lively, nostalgic atmosphere that brings early 2000s energy to the night.
22&CoThe Rotary Club of Key West Weekly Meetings
Weekly meetings of the Rotary Club of Key West bring together community leaders, professionals, and other service-minded people to connect, exchange ideas, and discuss projects that create positive impact locally and globally. Each gathering offers time to learn from one another, collaborate on service initiatives, and build lasting friendships. These meetings welcome long-time Rotarians as well as those interested in learning more about the club and ways to contribute to the Key West community.
The Rotary Club of Key West 1107 Key Plaza, Box 294 , Key West, FL, United States, Florida 33040Lobsterfest Dinner!
Savor a special one-night edition of a weekly Lobster Fest featuring Executive Chef Keith St. Peter alongside a storyteller who shares the history and culture behind each course. At the heart of the experience is the signature Lobster Enchilados, a favorite in Key West, showcased within an island-inspired menu. The meal includes crisp plantain chips, sangria, creamy lobster bisque, Lobster Enchilados served over white rice, and guava bread pudding. Two seatings are available so attendees can enjoy the courses and stories at a comfortable pace.
Key West Cooking ShowChef's Encore
Executive chef Keith St. Peter launches a monthly supper series that lets his creativity and knife work take center stage. This installment spotlights the bold, vibrant cooking of Yotam Ottolenghi, embracing a vegetable-forward, sunlit Levantine spirit. Guests can look forward to a colorful, globally influenced menu layered with bright flavors, varied textures, and unexpected depth. It offers a taste of why Ottolenghi draws so much excitement in London, without the need to travel abroad.
Key West Cooking Show2nd Annual Tats for Teachers
The second annual Tats for Teachers at Tattoos & Scars Saloon celebrates and supports Key West educators who devote time and personal resources to help students succeed. All sales made during the event are donated directly to Key West High School teachers and their classrooms. Guests can contribute by ordering food and drinks, purchasing items from the teachers’ Amazon wish list, dropping off school supplies at the bar ahead of time, or making a donation. The evening includes a hot wing eating contest featuring teachers, along with raffles, giveaways, and hot wings available for donations. Teachers, parents, students, local businesses, and community supporters all play a role... every purchase, contribution, and shared post helps equip classrooms. Building on last year’s strong community response, the focus is on ensuring teachers have the supplies they need to start the school year.
Tattoos & Scars SaloonFabulous Spectrelles
Celebrated as Key West's longest running musical revue, The Fabulous Spectrelles have entertained audiences for more than 43 years. This lively production honors the Motown and doo wop classics of the 1950s and 60s with vibrant energy and rich harmonies. The group appears in residence at The Key West EmPOURium, with performances hosted in the Karaoke Lounge.
Kaya Island EatsLobsterfest Duval Crawl
Celebrate the 28th annual edition of the Lobsterfest pub crawl with a festive circuit of participating bars. Each ticket includes an official Lobsterfest T-shirt, a keepsake lanyard, and access to special pricing on Sun Cruiser Iced Tea and Cuervo 1800 Tequila. Admission is $25 in advance or $30 at the door, and a portion of proceeds benefits the Key West High School Scholarship Fund.
Duval StreetKaraoke Night
Karaoke Night takes over Boardwalk Bar & Grill in Big Pine Key. Step up to the microphone, belt out favorite songs, and enjoy drink specials. It is a lively choice for a memorable evening with friends.
Boardwalk Bar & GrillBloody Birthday Bash
Celebrate a birthday by supporting a lifesaving cause at a poolside blood drive. Donate a pint, then enjoy a pint or choose a Bloody Bourbon once your donation is complete. A mobile blood donation bus will be stationed by the pool for an easy, sun-filled way to help. As the gathering winds down, the Lobster Fest Pub Crawl kicks off, keeping the carnival energy going. The focus is on securing much needed donations for the blood bank while creating a festive atmosphere.
The Marker Key West ResortFlamingos Pool Party
This poolside celebration brings together Four Flamingos for a Key West and Orlando collaboration that highlights coastal flavors. Guests and locals can enter at no cost, with live music and tropical vibes throughout. Chef-crafted lobster dishes will be available to purchase from both locations, including a Tropical Lobster Salad from Four Flamingos Key West for $15 and a Lobster Roll from Four Flamingos Orlando for $15.
Lobster Fest Dinner
Get ready for a special Lobster Fest one-night dinner at the Key West Cooking Show. The menu features crispy plantain chips, refreshing sangria, creamy lobster bisque, and lobster enchilados served over white rice, with guava bread pudding for dessert. Executive Chef Keith St. Peter will be featured, and there’s also storytelling that brings the dishes to life with the history and culture behind the flavors.
Key West Cooking ShowAugust's Community Swim
At the Shores Pool, a community swim offers live music, complimentary swag, and an appearance by Mermaid Dorian. It is part of a monthly series that is open to the public.
Dewey Deck at Southernmost Beach ResortTRX/Yoga
Enjoy a 60 minute session in a shaded tiki by the water that blends yoga with TRX to build balance and strength while helping you settle more deeply into postures. The bodyweight approach is easily adjusted to match individual goals and abilities, making it welcoming for all ages and experience levels. Suggested donation is $15. It offers a fun, distinctive practice in a small waterfront setting.
Oceanfront ParkSave-A-Turtle at Caturdays
Save-A-Turtle partners with the Sloppy Joe’s Foundation for Caturdays at Sloppy Joe’s Bar in Key West, offering a lively way to support sea turtle conservation while enjoying the local scene. Volunteers share how the organization protects endangered and threatened sea turtles across the Florida Keys and outline practical ways to help. Donations support nest monitoring, education programs, community outreach, rescue work, and other conservation projects that make a real impact. As a thank you, donors receive the event’s blinking cat ear headband, a playful Key West tradition that lights up Duval Street while backing a meaningful cause. Locals and visitors alike can connect with the team, learn more, and contribute to protecting the sea turtles that call the Florida Keys home.
Sloppy Joe'sLobster Roll Contest & Pool Party
Enjoy a free-admission pool party featuring lobster-themed food and drink specials. Take part in lobster hunts, try for door prizes, and soak up the fun throughout the event. Festival sponsors include Sun Cruiser Iced Tea and Cuervo 1800 Tequila.
Southermost Hotel At The BeachFarm Open House
A public open house takes place at Monroe County Sheriff's Office Animal Farm. Admission is free, and donations are appreciated.
Monroe County Sheriff's Office Animal FarmKey West Artisan Market
Head to Higgs Beach for the Key West Artisan Market, a relaxed outdoor event featuring local artists, makers, and food vendors. You can browse handmade goods, original art, fresh foods, and unique gifts, all while enjoying the island atmosphere with live music. The market is free and open to the public.
Clarence S.Higgs Memorial BeachLobsterfest Brunch
Savor an indulgent lobster-themed brunch amid lush tropical surroundings.
First Flight Island Restaurant & BreweryThe Quickening Soundcheck Set
Catch The Quickening for a special soundcheck set at Green Parrot Bar. The band will play a single 90-minute performance, with music described as funkified and feel-good, leaning into the vibrant energy of New Orleans.
Green Parrot BarAaron Hudgins
Enjoy live music with Aaron Hudgins at Rick's Bar Key West. The show runs from 8:00 PM until 11:59 PM, and it takes place on the downstairs stage at Rick's Bar.
Rick's BarMonday Night Catch the Mania Trivia
Put your knowledge to the test at a lively night of Catch the Mania Trivia, hosted by Megan on the mic. Teams and solo players are welcome, with a fast-paced format and plenty of friendly competition. Arriving early can help secure a spot and gives time to enjoy dinner specials from the kitchen. Happy Hour and drink specials are available. Compete for drinks and prizes while enjoying service from the Boardwalk team.
Monday Night Commander
Play Commander and have a chance to take home free promotional items and prize product.
First Flight - Key West, FL
Nick Norman appears at First Flight.
Charles Miller
Enjoy a live music performance by Charles Miller at Rick's Bar Key West. The show runs in the evening with music from 7:00 PM to 11:00 PM, hosted on the downstairs stage.
Rick's BarTRX/Yoga
Take part in a 60 minute class held in a shaded tiki by the water that combines yoga with TRX to develop balance and strength while helping you move deeper into each pose. TRX, much like yoga, is a bodyweight approach that can be adjusted to your goals and experience, making it welcoming for all ages and skill levels. Suggested donation is $15 for this fun, different practice.
Oceanfront ParkBusiness After Hours
An informal monthly networking gathering from the Greater Key West Chamber of Commerce brings together member business professionals to spark new connections and strengthen relationships. Attendance typically ranges from 50 to 75 participants, creating plenty of opportunities to exchange ideas and talk business in a friendly, relaxed setting. Admission is $10 for Chamber members and $20 for nonmembers. Each month a different Chamber business hosts to showcase its workplace, providing food, beverages, and at least one door prize, with the Chamber promoting the event through its media outlets.
Keys DermatologySpider-Man: Brand New Day
Peter Parker has faded into obscurity and lives alone, dedicating himself entirely to life as Spider-Man. As the strain builds, it sparks a risky transformation that draws out a formidable new adversary. Rated PG-13 and running 2 hours and 25 minutes.
Joe the Show
Joe the Show is playing live on the downstairs stage at Rick's Bar in Key West. The music runs from 7:00 PM to 11:00 PM on Tuesday evening.
Rick's BarKey West RumFest
Key West RumFest is a lively island celebration focused on rum tastings, handcrafted tropical cocktails, and great entertainment. Expect live music, plenty of Key West charm, and a laid-back weekend atmosphere filled with fun, flavor, and coastal energy.
Casa MarinaEuchre with the Brewer.
Enjoy a relaxed Euchre gathering that welcomes all skill levels. No prior experience is required, and friendly guidance is provided to help new players learn as they go.
DJ Todd
Catch DJ Todd for live music at Rick's Bar in Key West. The event runs late into the night, so plan for an extended set and a fun night out along Duval Street.
Rick's BarMeditation with Allen
Take a peaceful pause in the middle of the week with Meditation with Allen in the MCC Key West Sanctuary. This quiet time centers on reflection, grounding, and renewal, offering space to breathe and reset. All are welcome to come as they are.
MCC Key West Sanctuary🧘♂️Meditation With Alan 🧘🏻♂️
Take a gentle break with a peaceful meditation session alongside Alan. Hosted in the MCC Key West Sanctuary, it offers a quiet space to slow down, breathe, and reset.
MCC Key WestOne Piece TCG - Thursday Night League!
This weekly One Piece Trading Card Game tournament offers promotional packs for all participants, with an exclusive winner pack awarded to the player with the best record.
Key West CollectiblesPokemon League - Every Thursday
Fans of the Pokémon Trading Card Game can gather in a relaxed league setting to enjoy matches and trades using their own cards. The focus is on friendly fun with fellow collectors and players. Participants can take part in games, swap cards, and have opportunities to earn prizes. It is a simple way to connect with a community that shares a love for building decks and playing Pokémon.
KW CollectiblesTaking Back Thursday's!
Relive the early 2000s at 22&Co with Joe during a Thursday celebration that channels the spirit of 2001. The throwback fun continues on Thursdays throughout 2026.
22&CoYoga for All
The session takes place next to the beach volleyball courts beneath a large shade tree. Mats are available to borrow, and participation is donation based.
Sombrero BeachJoe the Show
Catch live performances with Joe the Show at Rick's Bar Key West. The show runs on Thursday evening from 7:00 PM to 11:00 PM at the downstairs stage.
Rick's BarEeland Stribling
Eeland Stribling brings his crowd-pleasing stand-up to Comedy Key West. Expect smart, adult comedy with plenty of stories, jokes, and a lively show in a small room. Doors open at 7:00 PM, and there is a two-item minimum for tickets. Seating is first come, first served, so arriving early is recommended for preferred spots. Due to adult content, the event requires guests to be 16 years old and up.
Comedy Key WestPrix-fixe Dinner in celebration of Key West Rum Fest 2026
Four Flamingos presents a ticketed, exclusive prix fixe dinner created in partnership with Papa’s Pilar Rum to honor Key West Rum Fest 2026. Chef Leo celebrates coastal flavors and island heritage with a curated menu, and every course is paired with Papa’s Pilar’s award-winning rums. Expect bold tropical notes, refined technique, and an energetic atmosphere that highlights rum culture and ocean-inspired indulgence. The evening brings together flavor and storytelling, sharing the tales behind the spirits and the pairings.
Four FlamingosFabulous Spectrelles
For more than 43 years, The Fabulous Spectrelles have presented a high-energy tribute to Motown and doo-wop hits from the 1950s and 60s. Recognized as the longest-running musical revue in Key West, this enduring show continues its residency in the Karaoke Lounge at the Key West EmPOURium.
Kaya Island EatsEarly Bird CleanUp along Northside Drive
Mount Sinai Multi-Specialty hosts a one-hour neighborhood litter cleanup focused on Northside Drive and nearby streets. Participants will meet in the facility's parking lot, where safety vests, buckets, and litter pickers will be provided. The brief effort is intended to make a noticeable impact and supports a cleaner, greener Key West.
Mount Sinai Specialty CareKaraoke Night
Karaoke takes over Boardwalk Bar & Grill in Big Pine Key, where guests can step up to the mic and belt out favorite songs while enjoying drink specials. Expect a lively, welcoming atmosphere with plenty of chances to perform, cheer on friends, and create a fun night of music.
Boardwalk Bar & GrillDJ Marty
DJ Marty will be performing at Rick's Bar Key West. Expect live DJ music all evening, running from 7:00 PM until 4:00 AM. The event takes place at 202 Duval St in Key West.
Rick's BarRum Fest Grand Tasting
At the Key West Theater, the flagship gathering of Key West Rum Fest brings together more than 30 rum brands from around the world in one place. Guests can sip and explore a wide range of expressions while meeting the makers, storytellers, and ambassadors who represent them. Each guest receives a commemorative tasting glass and a Rum Fest swag bag filled with items from participating brands. The focus is on discovery, connection, and the shared spirit of the rum community. Attendance also benefits The MARC House, the festival’s official charity partner, supporting meaningful work in the Keys.
Key West TheaterJesse Rice
Presented by Rum Fest Key West, this 21 and over event features Jesse Rice with Dawson Wright and Berkley Lindley. Rice is a songwriter and artist recognized by the ACM, AMA, CMA, Billboard, BMI, SESAC and the Trop Rock Music Awards. He co-wrote Cruise for Florida Georgia Line, a record-breaker that sold 15 million downloads, became the first country single to receive RIAA Diamond certification, held the number one spot on Billboard for 24 consecutive weeks and earned honors such as CMA Single of the Year, Billboard Country Song of the Year and SESAC Song of the Year. His writing also includes A Little Dive Bar in Dahlonega on Ashley McBryde’s Grammy-nominated Girl Going Nowhere. Artists including Florida Georgia Line, Nelly, Chase Rice, Kristian Bush of Sugarland, Ashley McBryde, Colt Ford and Robert Randolph have recorded his songs, and he has collaborated with Lady A, Dan + Shay, Cole Swindell, Russell Dickerson, Jon Pardi, Jordan Davis, Jelly Roll, Florida Georgia Line, Colt Ford, Sam Hunt and Chase Rice. As a touring performer, he continues to grow The Pirate Sessions series. Volumes I and II include guest appearances from Florida Georgia Line and Chase Rice and feature Gettin Down In A Pirate Town, which has been streamed more than 30 million times. The Pirate Sessions III reached number five on the iTunes Country Albums chart, its single Hope Town received regular play on SiriusXM’s Radio Margaritaville and the project led to a performance slot at the Trop Rock Music Awards along with a Horizon Award. The Pirate Sessions IV returned the series to the iTunes Country top five and entered the Billboard Country Albums top 40, while Go Away Cloud spent multiple weeks at number one on the Radio Trop Rock chart and remains in regular rotation on SiriusXM’s Radio Margaritaville. Most recently, The Pirate Sessions V topped the iTunes Singer-Songwriter chart, its lead single Sand in My Seat earned regular play on SiriusXM’s Radio Margaritaville and was named Radio Trop Rock Song of the Year, and the album received Album of the Year at the Trop Rock Music Awards.
Key West TheaterNative Plant Sale: Grow Your Own Habitat!
Plant it, care for it, and watch it flourish at a native plant sale designed to help you create habitat at home. Explore a thoughtfully selected range of plants adapted to Key West’s climate, chosen to support pollinators and wildlife while strengthening the island’s natural communities. Nursery professionals and volunteers offer personalized guidance to match plants with your light, space, and landscaping goals, whether you are starting from scratch or refreshing an existing garden. Choosing native species can save water, reduce reliance on pesticides, simplify upkeep, and contribute to long term ecological health. The Compost Village adds a sustainable boost, with kitchen scrap drop off, live composting demonstrations led by UF/IFAS Master Gardeners, and finished compost available to give new plantings a strong start. The day also features a Nature is ART Children’s Nature Art Workshop, priced at $10 and free for members, and a relaxing Prime of Life Yoga session (Yoga after 50) offered as a $20 drop in. The Key West Botanical Garden Society, Inc. is a 501(c)(3) nonprofit, and the Garden is a public, passive, natural resource focused outdoor recreation area.
Key West Tropical Forest & Botanical GardenSave-A-Turtle at Caturdays
Save-A-Turtle teams up with the Sloppy Joe’s Foundation for Caturdays at Sloppy Joe’s Bar in Key West, a lively fundraiser that highlights sea turtle conservation in the Florida Keys. Volunteers are on site to share how Save-A-Turtle protects endangered and threatened sea turtles and to explain simple ways to help through donations. Contributions support nest monitoring, education programs, community outreach, rescue efforts, and other conservation projects that make a difference for local wildlife. Donors receive the event’s blinking cat ear headband, a playful Key West tradition that lights up Duval Street. Learn about the mission, meet the volunteers, and support meaningful work for Florida Keys sea turtles in a spirited Key West setting.
Sloppy Joe'sTropical Heat's Five-Alarm Pool Party
A high-energy firefighter themed pool party sets the scene on the pool deck, complete with cool bursts from a pool boy CO2 cannon. Expect men bringing the heat and cold cocktails that come together for a sizzling summer memory with friends. All gay, bi, trans, queer, and brothers are welcome.
Island HouseEeland Stribling
Enjoy a night of stand-up with Eeland Stribling, a Denver-based comedian known for his sharp, story-driven style and frequent appearances across the comedy circuit. The show has a two-item minimum, seating is reserved but first-come, first-served for seating placement, and groups who bought tickets together will be seated together. Due to adult material, attendees must be at least 16 years old. Please arrive early to get the seats you want.
Comedy Key WestMichael Corelto
Catch Michael Corelto for a live music set at the downstairs stage at Rick’s Bar in Key West. The show runs from the evening through just before midnight.
Rick's BarGold Pool Parties
Island House marks 50 years with a monthly series of Gold Pool Parties featuring gold themed decor, cups, balloons, crowns, and gold clad pool boys, with more in store. This edition is the Tropical Heat Edition and is part of a yearlong celebration that also includes Members Appreciation, Pride, Fantasy Fest, and a 50th Anniversary Weekend Bash, closing with a festive year end finale. Please bring a photo ID. Admission is $50, payable in cash or by credit card at the door. Gay, bi, trans, and queer brothers are welcome.
Island HouseJust George
Catch Just George live at Rick's Bar Key West on the downstairs stage. The music runs from 3:00 PM to 7:00 PM, right on Duval Street.
Rick's BarTrivia Night Mondays
Join a fun Monday trivia night at the Key West Cooking School, with brain teasers across pop culture, history, food facts, and island trivia. You can come as a team or solo, compete for prizes, and enjoy a special trivia-night menu along with drink specials during the event.
Key West Cooking ShowJoe the Show
Joe the Show is performing live at Rick's Bar in Key West. The event runs from 7:00 PM to 11:00 PM on Tuesday evening, with music on the downstairs stage.
Rick's BarAndrew B.
Catch Andrew B. live at Rick's Bar in Key West. The performance runs Wednesday evening from 7:00 PM to 11:00 PM on the downstairs stage.
Rick's BarJoe the Show
Catch Joe the Show live at Rick's Bar in Key West. The show runs from 7:00 PM to 11:00 PM on Thursday, Aug 20, 2026, with performances happening on the downstairs stage. Plan to arrive a little early to get comfortable before the music starts.
Rick's BarDJ Marty
Enjoy DJ Marty live at Rick's Bar in Key West. The set runs late, starting Friday evening and continuing until the early morning hours. Stop by for a night of music at the bar on Duval Street.
Rick's BarBuckcherry
Rams Head presents Buckcherry at Key West Theater for a 21+ crowd. Known for high-intensity live shows, the group brings traditional hard rock shaped by more than two decades together. Their ninth studio album, Hellbound, made with producer Marti Fredrickson, spans driving rockers, mid-tempo cuts, and ballads, with tracks including Barricade, Junk, the title song Hellbound, No More Lies, Ain’t Wasting No More Time, The Way, So Hot, 5-4-3-2-1, Here I Come, and Gun. From a first gig at a house party to platinum and gold records and millions of fans worldwide, the band’s journey underlines a resilient spirit that continues to fuel the stage.
Key West TheaterHarley Ray
Catch Harley Ray live at Rick’s Bar Key West. This Sunday afternoon set runs from noon to 4:00 PM, with the performance taking place on Rick’s Downstairs Stage.
Rick's BarCaptain Buckles
Captain Buckles is performing at Green Parrot in Key West. The show starts at 5:30 PM.
Green Parrot BarJust George
Catch live music with Just George at Rick's Bar Key West on the downstairs stage. The set runs from mid-afternoon into the evening, so swing by anytime during the listed hours for good local vibes.
Rick's BarTrivia Night Mondays at Key West Cooking Show
Get ready for a fun, food-filled trivia night at the Key West Cooking Show. This weekly event runs Mondays from 6:00 PM to 8:30 PM, with questions covering pop culture, history, food trivia, and island oddities. Form a team or come solo, enjoy the special trivia-night menu and drink specials while you play, and compete for prizes and possible surprises for creative answers.
Key West Cooking ShowJesse Lee
Catch live music with Jesse Lee at Rick's Bar Key West. The performance runs Tuesday afternoon through early evening on the Downstairs Stage.
Rick's BarDolphin Sunset Celebration
Experience a new, once-a-month after-hours evening at Dolphin Research Center that begins as the sun sinks toward the horizon. After the gates close, an intimate program focuses on close-up moments with dolphins, expert conversations, and a sunset toast in the Florida Keys. Participants help with the dolphins’ evening enrichment by hand-feeding a favorite treat made with dolphin-safe gelatin, creating a warm, up-close interaction. Marine mammal professionals are available for casual Q&A and behind-the-scenes insights into intelligence, training, behavior, and conservation. As golden hour gives way to twilight, the evening includes a glass of champagne and the relaxing backdrop of waves, dolphin vocalizations, and colorful skies. Space is limited and the experience is offered monthly. Members can check their email for a booking code to access member pricing.
Dolphin Research CenterAndrew B.
Catch Andrew B. live at Rick’s Bar Key West. This performance runs from 7:00 PM to 11:00 PM, taking place on the downstairs stage at the bar.
Rick's BarJoe the Show
Catch Joe the Show at Rick's Bar in Key West. The live music event runs from 7:00 PM to 11:00 PM on Thursday, Aug 27, 2026, and will take place on the downstairs stage.
Rick's BarKey West Brewfest 2026
Key West Brewfest is a multi-day, island-wide celebration for craft beer lovers, bringing together breweries from across the country and local favorites. Across the weekend, you can enjoy exclusive tastings, tap takeovers, beer dinners, food pairings, brewery meet-and-greets, and themed events hosted at restaurants, bars, and resorts throughout the island. The weekend’s highlight is the Grand Tasting at Southernmost Beach Resort, with live entertainment and a laid-back Key West vibe.
Southernmost Beach Resort & GuesthousesReggae Lou & The Kind Budz
Reggae Lou & The Kind Budz take the stage at Key West Theater for a reggae performance. Fronted by award-winning artist Reggae Lou, the group has spent almost twenty years refining its sound while touring widely, from Michigan and Florida to Mexico, the East Coast, and the U.S. Virgin Islands. Now based in Key West, they hold several weekly residencies that keep the local scene energized. Their history reflects dedication and resilience, moving through challenges with daily hard work. Entry is restricted to attendees 21 and over.
Key West TheaterTrenton Chandler
Enjoy live music with Trenton Chandler at Rick's Bar Key West. The performance runs Sunday afternoon into the evening, taking place on the downstairs stage. Plan to drop by during the 4:00 PM to 8:00 PM window.
Rick's BarTrivia Night Mondays
Test your knowledge and taste buds at Trivia Night at the Key West Cooking School. Teams are welcome, or you can come solo and meet other trivia fans, with questions spanning pop culture, history, food facts, and local island oddities. Enjoy a special trivia-night menu and bar drink specials while you play, with prizes for the top scorers and potential surprises for creative answers. This event is free, but spots can fill up fast, so reserving ahead is recommended.
Key West Cooking ShowEarly Welcome: Island Adventure Sand Bar
Ease into island time on a relaxed backcountry outing with Fury Water Adventures Key West. Step aboard a Corinthian catamaran and cruise to a quiet sandbar or shallow-water hideaway in the Marine Sanctuary, where the afternoon is yours to paddleboard or kayak across clear water, watch for local wildlife, or unwind with your feet in the sand and a chilled drink. Designed with Just a Few Friends guests in mind and open to everyone, this all-inclusive experience provides lunch along with beer, wine, seltzers, soda, and water. Equipment and instruction are included, creating an easy and social way to enjoy the natural side of Key West before the music and festivities begin. Tickets are $119.95. Not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprise.
Fury Water AdventuresPre-event Official Meetup at the Chart Room
Ease into the days ahead with an informal meetup at the Chart Room inside Pier House Resort & Spa. Attendees can drop in at their convenience to connect with the Key West Parrot Head Club and fellow festival goers before the celebration begins. This historic bar, once visited by a famed island songwriter, provides a laid back setting for conversation, story swapping, and new connections. There is no cost to attend, and everyone is welcome. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprise.
Pier House Resort & SpaJohn Frinzi & Aaron Scherz
John Frinzi and Aaron Scherz team up in the Back Stage Listening Room at Key West Theater for a performance shaped by coastal storytelling and easygoing, beach-inspired sounds. This event is for ages 21 and over. A multi-platinum songwriter and producer, Aaron Scherz grew up on the music of Jimmy Buffett, John Denver, and James Taylor, and built a career tied to tropical travels, sailing culture, Parrotheads, Meeting of the Minds, and the Coral Reefers. His songs often celebrate a laid-back island lifestyle, and his credits include cuts by Keith Urban, Maddie & Tae, Tracy Lawrence, Reba McEntire, and more. His music can be heard on Radio Margaritaville and on stage with John Frinzi and members of the Coral Reefers. John Frinzi blends folk, pop, and country with a sunny coastal vibe. An early demo caught the ear of Doyle Grisham of Jimmy Buffett’s Coral Reefer Band, leading to the debut album "Into The Dawn." The follow-up, "Shoreline," highlighted his range through collaborations with Tom Corcoran, co-writer of Buffett favorites "Fins" and "Cuban Crime of Passion." Frinzi later partnered with Scherz on the EP "Blue Sky View" and singles including "Florida Man," with tracks in regular rotation on SiriusXM’s Radio Margaritaville. His performances span national tours, shows in the Caribbean and Europe, appearances at festivals such as Musikfest, the Keith Sykes Songwriters Celebration, the Key West Songwriters Festival, and the Pensacola Beach Songwriters Festival, and stage time alongside artists like Jesse Winchester, Mac McAnally, Ricky Skaggs, the Coral Reefer Band, Todd Snider, and Maria Muldaur.
Key West TheaterFriends of Bubba Festival HQ
Festival Headquarters at Key West First Legal Rum serves as a central hub for the week. Attendees can pick up a souvenir charity event badge and swag, check for the most up-to-date schedule information, and meet other participants as the festivities progress around the island. It is a convenient place to regroup when arriving or moving between happenings. The bar will offer its signature cocktails, including refreshing piña coladas, and badge holders receive a $1 discount. The souvenir charity event badge supports community causes, with all proceeds benefiting Reef Relief, the Bahama Village Music Program, and scholarships for local high school students. Admission is free and open to everyone. Events connected with this gathering are not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprise.
Key West First Legal RumA Pirate Looks Back
At Comedy Key West, A Pirate Looks Back offers an all-inclusive dine-in musical tribute to the period when a young Jimmy Buffett found his voice in Key West. Caleb Hogan, an acclaimed musician, actor, and Buffett historian, appears in character for a performance that blends live music, storytelling, humor, and island nostalgia. The experience pairs the feel of lunch theater with a tribute concert and a guided journey into the island’s creative, bohemian past, capturing the songs, spirit, and stories that helped shape a movement. It is billed as Key West’s only all-inclusive dine-in musical tribute. Each all-inclusive ticket includes a cheeseburger with chips and one drink from the lunch menu, with additional beverages and drink specials available for purchase. Tickets are $56.88. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Comedy Key WestTruman Waterfront Farmers Market
At Truman Waterfront Park, this outdoor waterfront market brings together a lively mix of local vendors and flavors. Browse stalls filled with fresh produce, local seafood, baked treats, tropical-inspired art, handmade crafts, boutique jewelry, and an array of international dishes. Stay refreshed with fresh-pressed juices, smoothies, and other cool beverages as you take in the ocean breeze and an easygoing island atmosphere. The market is organized by Jill and Sean of Just a Few Friends, with additional seating available for their guests to relax by the water and enjoy a casual picnic. Admission is free, families and pets are welcome, and paid parking is available.
Truman Waterfront ParkChart Room Daily Hangout Headquarters
At Pier House Resort, the Chart Room becomes an easygoing daily headquarters for Just a Few Friends, rooted in the lore of Key West. Long before fame, a young musician played here for tips and met his future wife, Jane, inside these walls. The room still feels timeless, small and softly lit, with warm wood and a nautical character that offers a calm retreat from the rush of Duval Street. Intimate and unpretentious, it carries stories in every surface, including the bar top where locals such as treasure hunter Mel Fisher are remembered in true Key West fashion. It is the kind of place you drift into, spot familiar faces, meet new ones, and feel connected without effort. Complimentary popcorn, peanuts, and the beloved Chart Dogs keep things simple while the conversation flows. Day or night, it is a welcoming gathering spot that feels unmistakably Key West. Open to all. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Pier House Resort & SpaTales From The Chart Room Bar
In the storied Chart Room at Pier House Resort, an intimate storytelling series unfolds in the very place where many of the tales first took shape. Hosted by Carol Shaughnessy, the first writer behind the Coconut Telegraph, a longtime member of the Margaritaville team, and former partner of Chart Room icon Phil Clark, each 30 minute session welcomes a special guest who shares firsthand memories from the island scene that helped shape the music, the lifestyle, and the community. There is no stage or formal production, just conversational storytelling in a room steeped in history. The pace is relaxed and guided, drawing out vivid details and personal connections, and no two sessions are exactly alike. At times the discussion opens to the room, adding a spontaneous and personal feel. Admission is free and open to the public, though space is very limited and entry is first come, first in. Sessions also stream on the Just a Few Friends Facebook page for those with a souvenir charity Event Badge. This event is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprise.
Pier House Resort & SpaCheese Burger Beach Battle and Tribute Concert
A beachside cookoff showcases eight of Key West’s favorite restaurants and caterers, each serving a tropical take on the classic cheeseburger, with tasting and voting to decide the champion. The reigning winner, Surly Siren, returns to defend the title against Margaritaville, serving side by side, along with six other contenders. Set by the ocean at Southernmost on the Beach, the tasting blends into a lively tribute concert as Gypsies in the Palace performs classic island favorites. Gates open with bars and food available, and burger sampling and voting take place during the early portion of the event. Tasting tickets are limited to 300. Expect beach vibes, live music, and great food. Tropical attire is encouraged, and flip flops are welcome. Outside food or alcohol is not permitted, and pets are not allowed. Low-back chairs and blankets are permitted, with limited rentals available. Presented by Just a Few Friends, Southernmost on the Beach Resort, and Faustos Food Palace. Not affiliated with or endorsed by the Jimmy Buffett estate or Margaritaville.
Southernmost Beach ResortOpen Mic / No Mic Night
At Andy’s Cabana, the open mic unfolds without a set list, letting the music evolve in real time. A changing mix of local players, visiting artists, and folks passing through trade tunes that might span island favorites, originals, country, rock, or something entirely unplanned. Expect a laid-back, neighborhood feel where all styles fit and the soundtrack is created on the spot. Musicians are encouraged to bring an instrument and step in when the moment feels right.
Andy's CabanaKeep it Going: Margaritaville Cafe After Party with Nadirah
After the Cheeseburger Beach Battle wraps up, the celebration moves to Margaritaville Café in Key West, a longtime gathering place filled with memorabilia, stories, and the island’s musical history. Guests can explore the displays, take photos, and settle in for live music led by Nadirah Shakoor and her band, with guest appearances by Claire Finley. With more than three decades of performances behind her, Nadirah delivers an upbeat set of fan favorites and strong musicianship alongside a seasoned group, all in a setting that captures the spirit of Key West. There is no admission charge. Seating is limited and offered on a first come, first served basis. Food and drinks will be available for purchase, and the venue is set in Old Town on Duval Street. This stop is part of the official Keep It Going weekend. This event is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
Margaritaville RestaurantJust a Few Friends Walking Tour
Enjoy a relaxed, 90-minute guided walk through Old Town that begins at Shrimpboat Sound, a humble recording studio that helped shape the music, stories, and spirit long associated with Key West. Visitors are welcome to leave a sticker or small keepsake there and take a moment to reflect before setting off. A guide leads a carefully mapped route through well known landmarks, hidden nooks, and longtime local hangouts connected to his life on the island. Along the way, hear lively tales from earlier days when the city drew artists, misfits, and free spirits, and learn how that creative energy influenced a musical style and a way of living that reached far beyond the island. The walk covers a couple of miles with a pause along the way and is considered moderate. Comfortable shoes, weather ready clothing, and water are recommended. Tickets are $45. All are welcome. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Shrimpboat SoundJust a Few Friends Celebration
Labor Day Weekend in Key West becomes a five day, island wide tribute with the 3rd annual Just a Few Friends celebration honoring the life, music, and spirit of the island’s favorite son. The experience stretches from Duval Street to the waterfront and out on the water, blending live performances, storytelling, art, film, and community moments across iconic spots and tucked away corners. Highlights span free and ticketed happenings. A free street concert features Gary & the Landsharks with hosting support from Sloppy Joe’s and Irish Kevin’s, and a free second line memorial procession led by Will Kimbrough and Howard Livingston makes its way along Duval Street to Truman Waterfront Park. At the park, a free community show brings together Howard Livingston & the Mile Marker 24 Band, Will Kimbrough, and Mac McAnally. Sunset Pier hosts free oceanfront sets by the Wheeland Brothers and by Cayman & The Mango Men. Ticketed options include Milagro Margarita bar strolls through Duval and the Historic Seaport with featured stops, cocktails, and live music, along with a cheeseburger contest and beach party at the Southernmost that serves up creative bites and tunes. Limited capacity Tales from the Chart Room sessions offer close up storytelling with artists, authors, and festival friends, while plein air art, author talks, book signings, and special film screenings bring the stories behind the music to life. On the water adventures such as sunset sails, sandbar trips, and island excursions add a salty twist, and pop ups welcome special guests including Coral Reefer favorites Nadirah Shakoor and Roger Bartlett. This is a multi venue celebration with a strong slate of complimentary concerts and community gatherings, paired with ticketed experiences and select limited capacity programming for those looking for more. A souvenir charity event badge is available to show support and connect with the community, with proceeds benefiting Reef Relief, the Bahama Village Music Program, and scholarships for local students. Badge holders receive perks such as early access to select experiences, local offers, and special touches throughout the weekend. Latitude Adjustment Hotel Packages bundle partner hotel stays with added benefits like priority access at key events and enhanced experiences for a seamless visit. Presented in part by the Monroe County Tourism Development Council. All events are not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprise.
Duval Street"Shrimp Boat Sound: Echoes From the Edge"
A panel discussion spotlights the feature documentary Shrimp Boat Sound: Echoes from the Edge, delving into the story of a renowned Key West waterfront recording studio at the southern tip of the United States that helped define Gulf and Western by blending country, rock, and island influences into a distinct sound. Director Michael J. Kirk leads an interactive presentation with select scenes and behind the scenes material, offering insight into the filmmaking process, the context behind interviews with artists and producers, and the studio’s role as both a creative haven and a spark for a genre. This is a presentation with clips, not a full film screening. Hosted by the Key West Art & Historical Society and moderated by Dr. Cori Convertito, the conversation includes special guests and unfolds in real time for a more personal connection to the legacy being documented. The film has not yet been released, providing an early look ahead of its journey through the festival circuit. Admission is $15 per person. Capacity is limited, and advance tickets are recommended. Air conditioned theater seating is available, and beer, wine, and concessions will be offered for purchase. Open to all. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprise.
Williams HallTales From The Chart Room Bar
Set inside a storied corner of Key West at Pier House Resort, this intimate storytelling series unfolds in the Chart Room itself, the place where many of the tales began. Led by Carol Shaughnessy, the original writer behind the Coconut Telegraph, a longtime member of the Margaritaville team and former partner of Chart Room figure Phil Clark, each 30 minute session welcomes a special guest to share firsthand memories from the island scene that helped shape the music, the lifestyle, and the community. There is no stage or formal production, just genuine conversation in a room rich with history. Through an easygoing, guided chat, Carol draws out vivid recollections, insider perspectives, and personal connections that defined an era, and no two gatherings are exactly alike. At times the discussion opens to the room, adding a spontaneous and personal touch. Admission is free and open to the public, but space is very limited and entry is first come, first served. Sessions also stream live on the Just a Few Friends Facebook page for those holding a souvenir charity Event Badge. Not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprise.
Pier House Resort & SpaThrough the Lens
Experience an intimate photographic look at the early concert years of Jimmy Buffett through a curated selection of vintage images by photographer Chris Lauber. Created in the 1970s as the sound and scene were taking shape, these photographs serve as firsthand records of a pivotal period, revealing the energy, spirit, and growth of an artist closely tied to Key West’s music history. Hosted at Pier House Resort & Spa, the installation is set in the lobby outside the Chart Room. Following his appearance as a featured guest at Tales from the Chart Room, Chris Lauber will open the show, meet attendees, share the stories behind the images, and provide personal context. The exhibition is free and open to the public and will remain on view throughout the festival. This event is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprise.
Pier House Resort & SpaDuval Street Party
Duval Street in Key West transforms into a Parrot Head celebration with a throwback concert that recreates the 1998 Meeting of the Minds street show, hosted by Sloppy Joe’s, Irish Kevin’s and Rick’s Place. The evening opens with Caleb Hogan delivering an acoustic set steeped in Key West storytelling. He also leads the first annual Bubba Look-Alike Showdown, presented by Hogfish Bar and Grill, where contestants bring their best ’70s Buffett-inspired look and performance, and the crowd selects the winner. Later, Gary & the Landsharks take the stage for a high-energy set that turns the street into a sing-along. Vintage tees and classic Parrot Head style suit the vibe, with plenty of chances to belt out familiar favorites. A souvenir charity event badge is available, offering early access perks while supporting local charities. There is no charge to attend and everyone is welcome. Presented in part by Milagro, Sloppy Joe’s, Irish Kevin’s, Rick’s and the Tourist Development Council. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Duval StreetBubba Look Alike Contest
The stage turns into a playful search for the best Bubba as part of a celebration recreating the 1998 Meeting of the Minds concert featuring Gary & the Landsharks, presented by Hogfish Bar & Grill. Anyone who has ever been told they resemble the beloved troubadour, from any era, is invited to capture the look, attitude, and easygoing presence that made Key West’s favorite son so iconic. Hosted by local Buffett tribute performer and Comedy Club lunch show host Caleb Hogan, contestants will step up one at a time, introduce themselves, pick up the provided guitar, and perform along to a randomly selected Buffett song while aiming to embody the character in front of a lively crowd. A panel of local representatives will narrow the field to three finalists, and the audience will choose the winner through live QR code voting. The champion earns the Golden Coconut trophy, a $1,000 cash prize, and ultimate festival bragging rights. Pre-registration is encouraged to secure a spot, with walk-up entries accepted if space allows. Participants should arrive early for check-in and staging. Costumes, props, and full character commitment are welcome, and the guitar will be ready on stage. Presented by Hogfish Bar & Grill, a Stock Island fixture long appreciated by Jimmy Buffett, whose friend and owner Bobby Mongelli helped shape the kind of unpretentious, local hangout the artist loved. Not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
Duval StreetJust a Few Friends: Early Bird Clean Up
Begin the day with a community plogging effort along the waterfront that supports Reef Relief’s work to protect the local marine environment. Organized by Keep Key West Beautiful, Just a Few Friends, Women's Fest, Conch Republic Seafood Company, Fury, and Reef Relief, participants can go solo or pair up to clean along Greene Street, Simonton Street, the Historic Seaport, and nearby Old Town areas. Check in at the bar at the corner of Greene and Elizabeth to grab a parking pass if needed, plus a safety vest, gloves, a bucket, and a litter picker. Everyone gathers afterward at Conch Republic Seafood Company, known locally as the Conch Farm, for complimentary juice and pastries and a group photo. Cleanup gear is provided, and each participant receives a sticker for a souvenir charity event badge. Bring a water bottle, dress for the weather, and wear closed-toe shoes for comfort and safety.
Reef ReliefIsland Time Breakfast
Start the morning with a relaxed island breakfast on the Historic Waterfront in Key West. Whether arriving after the Harborside Cleanup, heading to the City Proclamation Ceremony honoring Jimmy Buffett, or simply looking for a welcoming place to gather, this easygoing meetup pairs a satisfying meal with breezy waterfront views. Presented by Concrete Public Seafood Company, the spread includes eggs, sausage, bacon, pancakes, and fresh fruit, with coffee or juice included. Bloody Marys and mimosas are available for purchase at a cash bar. Pre-registration is preferred, and walk-ups are accepted as space allows. Seating is first come, first served. Come as you are, and feel free to take part even if you are not attending other activities.
Conch Republic Seafood CompanyKeep It Going… Hog’s Breath Saloon After Party
After the Duval Street concert winds down, the celebration continues at Hog’s Breath Saloon in Key West with a lively late-night scene. Expect a bustling crowd, cold drinks, and a friendly mix of locals and visitors keeping the momentum going. Gulfstream provides the soundtrack, a feel-good group led by singer-songwriter Andy Mauerman that blends modern country, classic rock, and coastal Americana into an easy, beach-ready groove. Sets move from laid-back rhythms to sing-along favorites, featuring songs by Kenny Chesney, Zac Brown Band, the Eagles, and Zach Bryan, with plenty of Jimmy Buffett in the mix. There is no cover, and a cash bar will be available. This event is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
Hog's Breath SaloonOutdoor Movie: Parrot Heads
Enjoy an outdoor movie night featuring a documentary that spotlights the Parrot Head community born from Jimmy Buffett’s music and relaxed, island spirit. The film blends rare interviews, concert footage, and fan voices to show how these songs helped create a far-reaching circle of flip-flop lovers and like-minded friends. Craft beers from the host beer company will be available, with wine for purchase as well, and a rotating selection of gluten-free menu options will be offered throughout the evening. Beach chairs are provided for comfortable seating beneath the night sky. There is no admission fee and everyone is welcome. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Southernmost Pint BrewpubGypsies In The Palace Buffett Tribute Band at Hogs Breath
Gypsies in the Palace brings a Jimmy Buffett tribute to Hog's Breath Saloon, celebrating the full songbook with both deep cuts and beloved favorites that longtime listeners recognize from the first chord. The atmosphere is relaxed, the storytelling takes center stage, and the music fosters the kind of connection fans share. You might hear Cuban Crime of Passion, Last Mango in Paris, or another tune you have not thought about in years but still know by heart. Admission is free, and the full menu and bar are available. Open to everyone. This event is not associated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Hog's Breath SaloonMargaritaville Beach House Pool Party
Poolside vibes await at Margaritaville Beach House Key West, set across from Smathers Beach and close to Old Town. Expect a relaxed scene with tunes, sunshine, and a friendly crowd. Order a drink, take a swim, or unwind by the water and enjoy an easygoing escape in a different corner of Key West. Admission is free and the public is welcome. Food is available and the bar is fully stocked. Resort casual clothing or swimwear is suggested. Seating is limited, so arriving early gives the best chance of finding a spot. A complimentary shuttle connects the resort with Old Town, including the Historic Seaport and Waterfront Brewery area. It departs from the resort at the top of each hour, and return trips from downtown leave on the half hour.
Margaritaville Beach HouseTales From The Chart Room Bar
Tales from the Chart Room is an intimate storytelling series at Pier House Resort that unfolds in one of Key West’s storied bars, right where many of these tales first took shape. Guided by Carol Shaughnessy, the first writer of the Coconut Telegraph, a longtime member of the Margaritaville team, and former partner of Chart Room icon Phil Clark, each 30 minute session welcomes a special guest who shares firsthand accounts from the island scene that helped shape the music, the lifestyle, and the community. These are not stage stories, they are the stories behind the scenes, told by the people who lived them. In a casual, guided conversation, Carol draws out vivid memories, insider perspective, and personal connections that defined an era. There is no stage and no formal production, just storytelling in a room with its own history. The atmosphere is close and conversational, and no two gatherings unfold the same way. At times the discussion includes voices from the room, adding a spontaneous and personal feel. Admission is free and open to the public, but space is very limited and entry is first come, first served. A live stream is available on the Just a Few Friends Facebook page for those with a souvenir charity Event Badge. These events are not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprise.
Pier House Resort & SpaGypsies In The Palace Buffett Tribute Band at Hogs Breath
Gypsies in the Palace brings a Jimmy Buffett tribute to Hog's Breath Saloon, exploring the full catalog with deep cuts and fan favorites that longtime listeners recognize from the first chord. The set may include songs like "Cuban Crime of Passion" and "Last Mango in Paris," along with tunes you have not heard in years but still remember. The experience balances laid-back storytelling, an easygoing groove, and a sense of community among fans. There is no cover, and the full menu and bar are available. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Hog's Breath SaloonMargaritaville Beach House Trivia Contest
Margaritaville Beach House Key West presents a laid-back trivia night celebrating Key West’s favorite son, with questions that span the songs, stories, lifestyle, and legends that shaped the music and the island. Play with a team or jump in solo and link up with new friends. Participation is free and a full bar is available. Prizes are awarded to the top teams. Arrive early to claim a spot. All are welcome, with a friendly atmosphere focused on good questions, great company, and plenty of laughs.
Margaritaville Beach HouseThe Wheeland Brothers and more
At Sunset Pier in Key West, The Wheeland Brothers share the stage with Mike Stack & Friends for an evening on the water that builds from laid-back sunset vibes to a lively dance floor. Mike Stack & Friends open with a collaborative, high-energy set that highlights where the local sound is headed, featuring Shareese, Marjory Lee, Pierce August, and D-Lew, along with a nod to the hometown favorite I’m From Key West. Later, Nate and Travis of the Wheeland Brothers deliver coastal originals that blend surf rock, reggae, and acoustic storytelling, with occasional nods to familiar favorites while keeping the focus on their own sun-soaked songs. Early access is available for Ultimate Friend and Best Friend VIP guests with table seating, followed by Souvenir charity Event Badge holders, then general admission. VIP guests can settle in early, order from the full menu, and enjoy frozen drinks as the waterfront sets the scene. The venue is open-air on the water with a full food menu and bar, limited table seating, and a standing room environment that encourages dancing. Arriving early helps with finding preferred viewing areas once doors open. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Sunset PierThrough the Lens
This photography exhibit spotlights concert imagery from Buffett's early years and takes place at Pier House Resort & Spa. Further information will be shared soon.
Pier House Resort & SpaParrots and Margaritas 5k Run/Walk
Parrots & Margaritas 5K returns for its third year with a festive run and walk presented by Kaya Island Eats. Participants can take on Duval Street at any pace and finish at Kaya Island Eats for a lively post-race celebration with margaritas and tropical music. The Flip-Flop Mile follows the main event for a more relaxed option and does not require completing the 5K, and a virtual format is available. Tropical attire is encouraged. Registration and payment are handled through Mile 0 Events, and advance registration is recommended. Entry is $46.99. Activities begin and end at Kaya Island Eats. All participants receive an event T-shirt, a souvenir margarita glass, admission to the celebration, one complimentary beverage choice of a margarita, Landshark beer, or a soft drink, and cheeseburger sliders with tater tots. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Kaya Island EatsKeep It Going After Party at the Back Yard EmPOURium
The celebration continues at Back Yard EmPOURium once the Wheeland Brothers finish at Sunset Pier. This relaxed, open-air spot blends the feel of a backyard hangout with a lively late-night gathering place, making it easy to swing by with friends, grab a drink, and keep the momentum going. The live music lineup will be announced, with a set planned to carry the evening forward. There is no cover charge, and beverages are available for purchase. The vibe is casual and welcoming. This event is not associated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
Back to the Island Beach Party
Experience a neighborhood bar transformed into a pop-up beach, with sand underfoot, tropical drinks, and music filling the air. 801 Bourbon Bar, a longtime local institution known for lively anything-goes energy, turns its space into a sand bar party right in Old Town. Tiki Man Radio will be on site throughout the day with B-Man and Mi-Shell, sharing island sounds and conversations that keep the vibe rolling. As an official stop on the Margarita Bar Stroll, it is the kind of place where a quick visit can easily turn into staying longer. Dance in the sand, sing along, or relax with a drink and take in the scene. There is no cover, drink specials are available all day, and swimsuits or tropical attire are encouraged. All are welcome. This celebration is not affiliated with or endorsed by the Jimmy Buffett estate or Margaritaville Enterprises.
801 Bourbon BarPaddle Out Tribute
Hosted by the Key West Parrot Head Club, this paddle out tribute honors the life, music, and legacy that bring the community together on the water at Smathers Beach near Margaritaville Beach Resort. Rooted in surf culture, participants head beyond the shoreline on boards, kayaks, or other floating craft, gather in a circle, and share a moment through silence, stories, reflection, or song before releasing flowers or other ocean friendly, biodegradable offerings into the water. Bring your own board, kayak, or float, or request to borrow one, with limited availability on a first come, first served basis. Comfortable swimwear is recommended. Exact launch information will be shared in advance, and plans depend on weather and water conditions. After the ceremony, the afternoon continues with a pool party at Margaritaville Beach Resort. This gathering is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
Smathers BeachRoger Bartlett Show with Emily Randle
Enjoy an intimate listening room performance at the Key West EmPOURium Listening Room featuring guitarist Roger Bartlett with violinist Emily Randle, presented by the Key West Parrot Head Club. Bartlett, Jimmy Buffett’s first lead guitarist and a founding figure in the original Coral Reefer Band, brings songs and stories from the early days of that sound to a close setting. His playing is heard on Come Monday, and he later reunited with Buffett during the making of Volcano. His work also includes the song Fool for a Blonde, featured in the film The Texas Chainsaw Massacre, along with a long career leading his own bands and performing in cities from New York to Las Vegas. Randle, an internationally recognized concert violinist and retired U.S. Army Sergeant Major, blends classical technique with contemporary styles, adding a vivid violin voice to the collaboration. The room is small and focused, ideal for listeners who want to connect deeply with the music and the stories behind it. This is a ticketed event with Early Bird admission at $20 and General Admission at $30. The event is independent of Jimmy Buffett’s Estate and Margaritaville Enterprises.
The Key West EmpouriumSecond Line Memorial Walking Parade
A community second line memorial procession honors a beloved Key West icon with a joyful tropical celebration of life and music. Guided by Will Kimbrough and Howard Livingston with special guests, the walk features live performances, communal singalongs, and a relaxed gathering by the water at Truman Waterfront Park. The route begins near the lower end of Duval Street, continues for several blocks down Duval, turns onto Southard Street, and proceeds to the park. Attendees can express their spirit with bright island attire, colorful umbrellas, decorated bicycles, handmade signs, and themed costumes. Musicians are welcome to add their sound, and spectators can cheer along Duval and Southard. A livestream will make it easy to take part from afar with watch parties at home or at bars. A $35 souvenir charity badge is available, with all proceeds supporting Reef Relief, the Bahama Village Music Program, and scholarships for local students. The procession emphasizes a litter free experience, with Reef Relief coordinating mobile cleanup teams and encouraging proper recycling and trash disposal. Getting around is easiest on foot, by bike, or via rideshare, since parking is limited near the start and finish. Bicycles may roll in the procession and can be secured at the park afterward. Reusable bottles are encouraged, and free water refills will be offered at Truman Waterfront Park courtesy of the Florida Keys Aqueduct Authority. Rooted in New Orleans and Caribbean traditions, a second line is a moving musical tribute where the community follows the band in celebration and remembrance. Admission is free and open to all. This event is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
Truman Waterfront ParkParty In The Park
The celebration moves to Truman Waterfront Park for a laid-back tribute to Bubba, unfolding after the Second Line arrives and setting the tone for a signature gathering of the weekend. Settle in on the lawn for live music, local flavor, and island spirit as Just a Few Friends honors the sounds and stories rooted in Key West. The lineup features Howard Livingston and the Mile Marker 24 Band, Will Kimbrough, and Mac McAnally, artists known for shaping the coastal soundtrack of the Gulf Coast and the Florida Keys. Expect breezy storytelling from Howard Livingston, seasoned musicianship from Will Kimbrough with the insight of a longtime collaborator, and songs delivered by Mac McAnally, a Grammy-winning songwriter and member of the Coral Reefer Band. Beyond the stage, the Key West Artisan Market pop-up brings a curated mix of local makers, artists, and food vendors. Bars and food stands are on site, cash and cards are accepted, and free water is available with reusable bottles encouraged. Seating options include a reserved area with chairs for Ultimate Friend and Best Friend VIP guests, a designated viewing area for Souvenir charity Event Badge holders where chair rentals are available, and open lawn seating for general admission where bringing a blanket or chair is welcome. The event is free and open to everyone, and lawn seating is first come outside of reserved areas. Parking is very limited, so consider rideshare, bikes, or the free Duval Loop. Please note that coolers, outside food or beverages, weapons, and drones are not permitted. Not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Truman Waterfront ParkMargaritaville Beach House Brunch
Ease into a relaxed brunch at Tin Cup Chalice Bar & Chill at Margaritaville Beach House, where live acoustic music sets the tone for a laid back resort atmosphere. A dedicated brunch menu highlights breakfast favorites and island inspired plates, along with cocktails and coffee. Order directly from the menu and linger as long as you wish, since reservations are not required and seating is open on a first come, first served basis. Resort casual attire is recommended. A complimentary shuttle connects the resort with Old Town, including the Historic Seaport and Waterfront Brewery area, with regular departures from the resort and returns from downtown. This event is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
Tin Cup Chalice Bar & ChillBBQ Rib Battle
Hosted by Shots and Giggles and The Key West Chamber of Commerce, the 7th Annual BBQ Rib Battle brings grill masters together for a head-to-head cookoff with cash prizes at stake. The event features a competition to watch along with homemade barbecue ribs, sides, music, and drinks.
Ann StreetPool Party at La Concha
Take in the scene from the rooftop pool deck at Crowne Plaza Key West La Concha, set above Duval Street with panoramic views of Old Town and the water. This laid back poolside gathering offers music, refreshing drinks, and an easygoing atmosphere whether you plan to cool off in the pool, lounge in the sun, or relax with a cocktail. The event is free and open to guests of Just a Few Friends. Access is through the hotel lobby. Resort casual attire or swimwear is appropriate. Hotel guests may use provided towels, while non hotel guests should bring their own. A full bar is available at the pool, and food can be ordered through the hotel. Seating is limited on a first come, first served basis, and capacity may be managed as needed. Outside food or beverages are not permitted. Not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
La ConchaTales From The Chart Room Bar
Settle into the Chart Room bar at Pier House Resort & Spa for a 30 minute storytelling session that unfolds where many of these tales were born. Host Carol Shaughnessy, the original Coconut Telegraph writer, a longtime member of the Margaritaville team, and former partner of Chart Room figure Phil Clark, guides a relaxed conversation with a special guest who shares firsthand memories from the island scene that shaped the music, lifestyle, and community. There is no stage or formal production, just candid stories in an intimate room, and each gathering has its own character. At times the discussion opens to the room, adding a spontaneous and personal feel. Free and open to the public, with very limited space and first come, first served entry. Sessions are also streamed on the Just a Few Friends Facebook page for those holding a souvenir charity Event Badge. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Pier House Resort & SpaIsland Adventure & Sunset Cruise Combo
An easygoing backcountry outing pairs a secluded sandbar stop with a sunset cruise in Key West. Over roughly three and a half hours, spend unhurried time in the water, try stand up paddleboarding, or paddle a kayak among the mangroves, then relax on the ride back with a drink as the colors shift across the sky. A light meal, snacks, and beverages are included, and kayaks, paddleboards, and floating mats are available. Plan to check in 30 minutes before departure, bring swimwear, a towel, sunscreen, and an ID, and note that alcohol is served only after water activities. Snorkeling is not part of this tour, and the sandbar visit depends on conditions. Space is limited, so advance reservations are recommended. All are welcome. This event is not affiliated with or endorsed by Jimmy Buffett’s estate or Margaritaville Enterprises.
Fury Water AdventuresIsland Tiki Sunset & Music Cruise
Set out on a floating tiki boat for an evening of live music by Cayman & the Mango Men, taking in the performance from the water just off Sunset Pier as the sky fades into sunset. The cruise lasts about two and a half hours and is designed for small groups, with up to six guests per boat. It is BYOB, with a cooler and ice provided, and glass is not recommended. There is no restroom onboard, so plan accordingly. Bluetooth is available for your own music, and boats are positioned offshore for the full concert experience. Dress for the weather and expect a relaxed, uniquely Key West way to enjoy the show. Availability is limited, so advance booking is recommended.
The Marker Key West Harbor ResortLast Call - After Party
After the last notes at Sunset Pier, the celebration continues at Smokin' Tuna Saloon with a free after party. As Just a Few Friends wraps another year in Key West, the festivities shift to the venue’s new home in the former Hard Rock Café building for a special late-night set from songwriter and musician Will Kimbrough, following Cayman Smith-Martin and the Mango Men. The updated space features a dedicated concert area tucked behind the restaurant, and this gathering is among its first major shows. Expect an easygoing finale with friends and live music. Admission is free, food and beverages are available for purchase, and seating is limited with standing room also offered. This event is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.
Smokin' Tuna SaloonKENNY from LANDFALL solo at Geiger Key Marina
Kenny from Landfall steps out for a solo debut at Geiger Key Marina, delivering a mix of Jimmy Buffett favorites, tropical tunes, classic rock, country, and singer songwriter picks, with a few surprises along the way. The marina offers a quiet waterfront setting not far from downtown Key West, framed by mangroves and working boats and known for memorable sunsets, fresh seafood, and an easygoing Old Florida vibe. It is a popular stop for boaters, anglers, and paddlers, and a welcoming place for anyone who wants to relax by the water while enjoying music that celebrates island life.
Geiger Key Marina and Fish CampNew Moon Magic w/Mermaid Dorian
Enjoy swimming, storytelling, and shipwreck history with Mermaid Dorian at South Beach. This free event welcomes all ages. Space is limited and reservations are required. To reserve, text "Save Me A Seat" to 717.816.4153.
South Beach, Key WestShaw Revolver
Shaw Revolver delivers a high-energy performance led by a family of musicians, featuring powerful vocals, close harmonies, and players who move between instruments. The show spans country, rock, blues, and folk, with a focus on engaging the crowd and welcoming attendees of all ages.
Kiki's Sandbar & GrilleKenny Live at Geiger Key Marina in Key West
Kenny performs live at Geiger Key Marina, nestled a short distance from downtown Key West. This waterfront hideaway offers mangrove scenery, working fishing boats and sunset views, all steeped in Old Florida character. Known for its relaxed vibe and fresh seafood, the marina is a popular stop for boaters, anglers and paddlers looking to avoid the crowds. The set features Jimmy Buffett favorites, tropical tunes, classic rock, country and singer songwriter hits, plus a few surprises. Guests can relax by the water with a cold drink, enjoy fresh seafood and take in the sunset while the music celebrates great songs, good company and island life.
Geiger Key Marina and Fish CampSeptember's Community Swim
At the Shores Pool, a community swim open to everyone features live music, complimentary giveaways, and an appearance by Mermaid Dorian. This is part of a monthly series.
Dewey Deck at Southernmost Beach ResortGrassy Key Paddle Battle
The Grassy Key Paddle Battle gathers paddlers at Grassy Flats Beach Club & Resort in Marathon in the Florida Keys, with racing split between the resort and Keys Cable. The distance event at Grassy Flats features Round da Duck, a 7 mile course with a $65 entry. Divisions include SUP 14 feet, SUP 12 feet 6 inches and under, OC1, OC2, and surfski. A captain’s meeting leads into competition, and awards are presented at the Palm Deck. Packet pickup is available. The SUP Sprint Battle takes place at Keys Cable with a $20 entry and a knockout heats format. Each competitor starts on the water in a dedicated lane, paddles 100 meters to a buoy, makes a left shoulder turn, then sprints 100 meters back to the finish for a total of 200 meters. A live cash pot is offered for the sprint race. The event seeds the pot with $50, racers may opt in with a $10 buy in, and separate pots are maintained for men and women. The buy in must be completed before racing begins, only participants who opt in are eligible for payout, and prizes are paid after the finals. The total pot is announced before the first heats. Grassy Flats offers event hotel pricing, including Wreckers Double Queen at $189, Wreckers King Room at $199, Humidor Suite at $229, Galleon Suite at $269, Conch House two bedroom at $349, and Conch House three bedroom at $399.
KENNY solo at Geiger Key Marina in Key West
LANDFALL’s Kenny Yarbrough brings a solo performance to Geiger Key Marina and Fish Camp in Key West, blending Jimmy Buffett favorites, tropical classics, classic rock, country, singer songwriter hits, and a few surprises. The music pairs with a waterfront setting framed by mangroves and working boats, where Old Florida character, relaxed vibes, and fresh seafood set the tone. Popular with boaters, anglers, and paddlers, this hideaway is known for peaceful views and memorable sunsets. Guests can enjoy fresh seafood, unwind by the water, and take in a laid back Keys soundtrack in a place locals treasure and visitors remember.
Geiger Key Marina and Fish CampDolphin Sunset Celebration
Experience an after-hours evening at Dolphin Research Center as the day fades into sunset. Guests can remain on site once the gates have closed for an intimate program focused on connection with dolphins and conversations with the experts who care for them. Take part in evening enrichment by offering dolphin-safe jello and enjoy up-close interactions. Marine mammal professionals will be available to discuss intelligence, training, behavior, and marine conservation, sharing stories and insights in a casual setting. As golden light turns to twilight, enjoy a champagne toast surrounded by the colors of a Florida Keys sunset, the sound of nearby waves, and the gentle calls of the dolphins. This offering is available once a month with limited availability. Members should check email for the current booking code to receive the member price.
Dolphin Research CenterGov't Mule & Ziggy Marley
Live Nation and Rams Head present a concert at Coffee Butler Amphitheater featuring Gov’t Mule with Ziggy Marley. This all ages event brings together exploratory rock and improvisation alongside reggae shaped by thoughtful songwriting. Guided by GRAMMY winner Warren Haynes, Gov’t Mule has spent more than three decades cultivating a worldwide following through fearless musicianship in the studio and on stage. The band has released over twenty studio and live records, including the 2023 album Peace...Like A River on Fantasy Records with guests Billy F Gibbons, Ivan Neville, Billy Bob Thornton, Ruthie Foster, and Celisse. The lineup features Haynes on guitar and vocals, Matt Abts on drums, Danny Louis on keyboards, guitar and backing vocals, and Kevin Scott on bass. Ziggy Marley, a nine-time GRAMMY and Emmy award recipient, has forged a distinguished career approaching forty years as a musician, producer, activist, and humanitarian. The eldest son of Bob and Rita Marley, he blends reggae with funk, blues, and rock, writing songs that address environmental stewardship, personal empowerment, social injustice, and political inequity, while returning to the unifying theme of love. Through Tuff Gong Worldwide and Ishti Music he maintains control of his masters and publishing, and his charity URGE supports children in Jamaica, Africa, and North America.
Coffee Butler AmphitheaterChef's Encore - Chef's Whimsy
An anything-goes supper club with no set theme. Executive Chef Keith Saint Peter cooks by instinct, letting inspiration shape the menu in the moment. The outcome is a singular meal that is bold, surprising, and impossible to duplicate. The focus is on creativity at the table and a spirit of playful unpredictability.
Key West Cooking ShowKey West OktoBREWfest
Raise a glass at the main tasting for Key West OktoBREWfest, featuring more than 60 beer vendors pouring over 225 varieties alongside live entertainment. Southernmost Beach Café keeps the celebration fueled with beer hall inspired food specials, and cocktails are on hand for anyone looking to switch it up. VIP tickets offer early entry to beat the crowd and include a commemorative poster, a stainless steel VIP mug, and a Bavarian themed buffet for $125. General Admission is $50. A Designated Driver option is available for $20 and includes entry, soft drinks, and a coupon redeemable for one food item.
Dewey Deck at Southernmost Beach ResortKey West ocktoBREWfest Grand Tasting Event
A grand tasting experience is on the way with two ticket options. General admission is 50 dollars. VIP admission is 125 dollars and includes two hours of early entry, a commemorative poster, a special VIP mug, and a Bavarian themed buffet. Tickets will be available soon.
The 11th Annual Jerry Garcia Birthday Bash
At The Green Parrot, the 11th Annual Jerry Garcia Birthday Bash features live renditions of Grateful Dead music by local favorites in a daytime setting. The celebration offers a welcoming atmosphere, a silent auction, and additional activities that pair music with a mission. Proceeds support Reef Relief’s Education and Conservation programs, which have reached 100,000 students and aim for the next 100,000.
The Green ParrotEarly Bird Clean Up Virginia & Watson Streets hosted by Unity of the Keys
Take part in a one-hour litter cleanup at Virginia and Watson Streets, hosted by Unity of the Keys. Participants will meet at Unity of the Keys to pick up a vest, bucket, and picker before getting started. After the cleanup, yogurt parfait will be available along with an opportunity to learn about Unity of the Keys. Streetside car parking is available. One hour can make a big difference.
Unity of the KeysSouthernmost Half Marathon & 10K
Runners take on a coastal challenge at the southernmost island in the contiguous United States, with a choice of a 13.1 mile half marathon or a 6.2 mile 10K. The route features sweeping ocean and gulf views and passes iconic Key West landmarks. The start and finish are set at Higgs Beach in Key West. Every participant receives an event T shirt at packet pickup and a finisher medal upon completing the race. Presented by Integrity Multisport.
Higgs Beach Key West, Florida37th Annual "Showcase of Key West Businesses" Tradeshow
Presented by the Greater Key West Chamber of Commerce in partnership with Mount Sinai, the 37th annual Showcase of Key West Businesses brings together companies and community members for an open-to-the-public tradeshow, followed by a members-only Business After Hours gathering. Co sponsors include New You Health Clinic, Greeen House, and Mount Sinai. Marketing support comes from Waste Management, Lower Keys Medical Center, Keys Federal Credit Union, and Hear 4 U Audiology.
Casa Marina Key West, Curio Collection by HiltonMrs. Roper Romp
Break out a caftan and that signature curly red wig for a groovy gathering filled with stunning sunsets, music, photo opportunities, dancing, trivia, games, prizes, and funtastic specialty drinks. Expect plenty of Three’s Company themed fun. This is not a ticketed event, and attendees are asked to bring rent money, with 100 percent of the rent going directly to a local charity. For more information, call 850-596-4065.
Sunset Pier ~ Key WestDolphin Sunset Celebration at Dolphin Research Center
A newly introduced after-hours evening at Dolphin Research Center invites guests to remain on site once the center closes to the public for a memorable program focused on connection and discovery. Take part in the dolphins’ evening enrichment by feeding a dolphin-safe gelatin treat by hand and enjoying close-up interaction. Marine mammal specialists host relaxed conversations, field questions about intelligence, training, behavior, and conservation, and share insider perspectives. As sunset deepens over the Florida Keys, the experience features a champagne toast with ocean sounds, dolphin vocalizations, and colorful skies setting the scene. Availability is limited and the event is scheduled monthly. Members receive a booking code by email for member pricing.
Dolphin Research Center