Events in Key West
The World Food Experience: Summer Solstice Celebration
The World Food Experience brings a Summer Solstice celebration to Mallory Square with bite-size tastings, artwork by local artists, and live entertainment. Attendees can savor small portions, explore creative works by local artists, and take in live acts throughout the celebration.
Mallory SquareKiki's Live Music
Jack Fivecoate brings live reggae to Kiki’s Sandbar, mixing familiar favorites with original songs. The sandy setting invites dancing with a drink in hand.
Kiki's Sandbar & GrilleJustin Angelo
Justin Angelo performs at Sunset Tiki, a relaxed tiki bar beside the pool at the Galleon Resort that serves tropical drinks and features live music. Settle in by the water for a casual atmosphere with cocktails and songs in a lively setting.
Sunset Tiki80s & 90s Trivia Night
Live team trivia at the Retro Room focuses on pop culture from the 80s and 90s. Teams of up to six players compete for prizes. It takes place every Sunday.
The Retro RoomKey West Artisan Market
Set in a laid-back island atmosphere, this open-air marketplace spotlights local artists, makers, and food vendors. Browse unique handmade goods and original artwork, and enjoy offerings from local food vendors.
Higgs BeachHot Rods & Dad Bods Car Show
Celebrate Father’s Day at the second annual car show featuring awards for Best Overall, Best Classic, and Most Unique. Families will find bounce houses, kids’ crafts, and face painting, while dad-focused vendors add to the fun. Enjoy live music by StormFront, a hot wing eating contest, and a Dad Bod contest, plus food and drink specials throughout the event. Car owners of all makes and models are welcome to participate, and pre-registration is available by emailing car details and contact information to info@boondocks.us.com.
Boondocks Grille & Draft House & Miniature GolfHod Rods and Dad Bods
A Father’s Day themed celebration at Boondocks Grille and Draft House features family-friendly activities such as contests, raffles, a silent auction, and more. Music is part of the festivities, creating a lively atmosphere for a full day of fun.
Boondocks Grille and Draft HouseFather's Day Float
Treat a favorite father figure to a three-hour sailing outing that includes a swim stop, brunch, and drinks. The experience takes place aboard Argo Navis, a 75-foot luxury vessel on the Gulf of Mexico, and is set up for time with family and friends. The price is $135 per person. Public outings aboard Argo Navis welcome dogs and are non-smoking. To reserve, call (305) 509-1771.
S/V Argo NavisHarley Ray at Rick's Bar Key West on Sunday, Jun 21, 2026
This live music performance features Harley Ray at Rick's Bar in Key West.
Rick's BarPickles Pub Wing Eating Competition
Pickles Pub Key West hosts a wing eating competition benefiting the Florida Keys SPCA. Participants compete for the title of ultimate wing champion.
Pickles Pub Key WestMike Mannarino at Tipsy Rooster Liquor Store and Bar on Sunday, Jun 21, 2026
Mike Mannarino appears at Tipsy Rooster Liquor Store and Bar.
Tipsy Rooster Liquor Store & BarThe Newtons at Key West EmPOURium on Sunday, Jun 21, 2026
A live music performance by The Newtons takes place at Key West EmPOURium.
Key West EmPOURiumCars & Coffee Key West
Cars & Coffee Key West is a car meet held at Denny’s Key West. The event welcomes vehicles of all years and makes.
Denny'sDJ Kori
DJ Kori performs at Rick's Bar in Key West, adding to the city’s live music scene across its bars and saloons. This appearance is included among local festivals and events, offering another option for nightlife entertainment in the area.
Rick's BarMagic of Frank Everhart at Schooner Wharf Bar & Grill on Sunday, Jun 21, 2026
Frank Everhart presents magic at Schooner Wharf Bar, carrying on a family tradition. His appearances at this Key West bar span 20 years, and he learned the craft from his father, who pioneered the Magic Bar concept. The performance reflects that long-running history and the legacy behind this style of magic.
Schooner Wharf BarDave Landau
Dave Landau takes the stage for a live stand-up performance at Comedy Key West in Key West.
Comedy Key WestYoung Writers Studio – Key West Literary Seminar
Applications are open for a five-day summer program focused on writing, offered by the Key West Literary Seminar for local high school students.
Elizabeth Bishop HouseMonday Night Catch the Mania Trivia
Catch the Mania Trivia delivers a lively competition hosted by Megan on the mic. Participants can play solo or form a team. Early arrival is recommended for seating and to enjoy dinner specials from the kitchen. Happy Hour is available, and drink specials continue throughout the event. Prizes are up for grabs, paired with the friendly service associated with the Boardwalk.
Monday Night Commander
Play Commander with opportunities to pick up free promos and prize product.
First Flight - Key West, FL
Nick Norman appears at First Flight in Key West, Florida.
Monday Night Jazz Jam
An upbeat jazz jam invites participation from both players and vocalists, as well as those who simply love live music. Look for recurring appearances by Skipper Kripitz, Larry Baeder, Terri White, Joe Dallas, Jeff Dalton, James King, Matthew White, Ronnie Lovely, and Aaron Luka, with additional guests rounding out the lineup.
Monday night jazz jams
Monday night jazz jams brings an evening of live music with a standout lineup. Enjoy cold drinks, refreshing cold air, a historic setting, and fantastic service from start to finish.
EARLY BIRD SPECIAL Mon-Fri 8-10AM - $10 BREAKFAST ALL SUMMER LONG
Wake up to a wallet friendly breakfast at Rams Head Southernmost Restaurant in Key West. The Early Bird Breakfast Special features a $10 breakfast. Pair it with fresh coffee and enjoy the relaxed island vibe. Whether fueling up before the beach, starting the workday, or savoring a slow island morning, it offers an easy, affordable start to the day.
"Island in the Works"
Island in the Works, part of the Young Writers Studio, invites high school writers to develop their voices, reflect on themselves, and see their island home in a new light. Based at the Elizabeth Bishop House, this five day program centers on site specific writing exercises and includes a day trip to Dry Tortugas National Park. It is open to students entering their sophomore, junior, or senior year in Fall 2026. Participants with demonstrated need are eligible for full financial support. The program is designed for students who are curious about the history of Key West and want to find their voice as writers.
Elizabeth Bishop HouseDrunk Spelling Bee
A Monday night tradition hosted by the comedians of Comedy Key West turns spelling into a tipsy competition. It begins with a beer chug, then contestants step up to spell their assigned words in front of the bar crowd. Some are precise, others are confidently off the mark, and the variety is part of the experience. Attendees can watch or take part and see who ends up on top, with prizes for the champions.
Mary Ellen's Bar & KitchenTrivia Night Mondays at Key West Cooking Show
At the Key West Cooking School, trivia takes center stage with a blend of palate-pleasing fare and friendly competition. The atmosphere is lively, with laughs and questions that keep everyone engaged, paired with food to match the energetic mood. It offers a flavorful twist on classic quiz night and a chance to combine good eats with brain-teasing fun.
Key West Cooking ShowCharles Miller
Charles Miller appears at Rick's Bar in Key West.
Rick's BarIndustry Night
Designed for hospitality professionals, this event offers a 20% discount to service industry workers and a chance to unwind on the customer side of the bar. Enjoy being the guest for a change while taking advantage of the savings.
The Retro RoomTrivia Tuesday at Mary Ellen's
Mary Ellen’s hosts a lively trivia night where participants can test their knowledge and compete for fun prizes. After the trivia wraps up, $8 draft cocktails are available.
Key West Investigation: America's Most Haunted Firehouse - Old Town, Key West
Step into one of Key West’s most active paranormal sites and take on the role of investigator at America’s Most Haunted Firehouse. The experience opens with an immersive audio tour that shares the real history of Old Firehouse No. 3, including tragedies and unexplained incidents tied to this historic building. After that introduction, the lights go out and the investigation begins. Explore the entire firehouse independently with ghost‑hunting tools and a flashlight as you work to piece together cold case mysteries and look for signs of the spirits said to remain. This is a hands‑on investigation rather than a standard ghost tour, inviting you to engage with the stories, examine the evidence, and note what you encounter. Capacity is limited to 13 people, and a portion of proceeds supports restoration of the historic Key West firehouse.
The Alex Vega Key West Firehouse MuseumEARLY BIRD SPECIAL MON- FRI 8-10AM - $10 BREAKFAST ALL SUMMER LONG
Rams Head Southernmost Restaurant in Key West features an Early Bird Breakfast Special with a $10 breakfast. It fits pre-beach plans, the start of a workday, or a leisurely island start, paired with fresh coffee in a relaxed setting. Enjoy a budget-friendly beginning to the day with easygoing Southernmost charm.
Summer Reading: Storyteller Windell Campbell
An expanded Summer Reading story time welcomes guest storyteller Windell Campbell. The session features engaging, interactive tales brought to life with puppets and other playful elements.
Big Pine Key LibraryJesse Lee
Key West highlights include live music, a variety of local festivals and other events, and happy hour offers at bars and saloons. Options span bed and breakfast stays, boat rentals in Key West, and accommodations at campgrounds and RV parks. Casual dining is available, deep sea fishing is an option, and Dry Tortuga is part of the mix.
Rick's BarEuchre with the Brewer.
A friendly Euchre session with the brewer welcomes all skill levels. Beginners receive instruction, so no prior experience is required.
TRX/Yoga
This 60 minute session takes place in a shaded tiki by the water at Oceanfront Park and is open to every age and skill level. It blends yoga with TRX to develop balance and strength and to help deepen yoga postures. Because TRX is bodyweight based, the work can be personalized to each participant’s goals and abilities. Suggested donation is 15 dollars.
Oceanfront ParkKiki's Live Music - Pierce August
At Kiki’s Sandbar, Pierce August delivers a lively blend of country and Americana tunes. Expect dancing in the sand, cold drinks, and an upbeat atmosphere that keeps the good times rolling from start to finish.
Kiki's Sandbar & GrilleSound Journey | DONATION-BASED with Ophelia
A donation-based sound journey led by Ophelia invites a spacious pause where the body can soften and the mind can settle. Held at Evolve Key West Temple, this gentle Yin and sound experience welcomes all levels. Expect fully supported yin postures that encourage the release of physical, emotional, and energetic tension, while soothing tones move through the room to calm the nervous system and guide you back to balance. There is nothing to push or perform, simply receive and rest. No prior experience is required, and everyone is welcome. Space is limited, so arriving early helps you settle in and create a personal sanctuary. The intention is that you leave feeling lighter, clearer, and quietly renewed from within.
BINGO & BEATZ with DJ Sanaris
Key West Theater presents a bingo night powered by DJ Sanaris, combining music with classic games. The grand prize awards the pot, and additional prizes include gift cards contributed by local businesses. This event brings together beats and bingo at the theater.
Key West TheaterDolphin Sunset Celebration at Dolphin Research Center
Experience an after-hours evening at Dolphin Research Center that unfolds after the gates close, offered once a month with limited capacity. Take part in the dolphins’ evening enrichment by offering dolphin-safe jello, creating a close, joyful interaction. Marine mammal experts will be available for relaxed conversations about intelligence, training, behavior, and conservation, sharing stories and behind-the-scenes insights. As the Florida Keys sky shifts from golden hour to twilight, enjoy a champagne toast while listening to the waves and the gentle calls of the dolphins. Members can check email for the current booking code to receive member pricing.
Dolphin Research CenterArts & Drafts
Explore your creative side while enjoying a beer or any beverage you prefer. A resident artist who also bartends leads a different lesson each week, and all materials are included.
The Retro RoomJukebox Wizard with Landon!
Jukebox Wizard turns Mary Ellen's into a high-energy Name That Tune game show hosted by Landon. He plays short song snippets and participants use their phones to enter the artist and title, keeping the gameplay simple and fast. The show is billed as Key West’s number one Name That Tune experience and moves in quick rounds that keep the excitement up. Guests can enjoy good food, refreshing drinks, plenty of music, and comfortably cool air conditioning throughout.
June's Pizza For Purpose with SOS Foundation
Pizza For Purpose supports SOS Foundation, with 15% of every dine-in and online order donated to their work. Proceeds help the organization advance a healthier Monroe County by widening access to food through distribution, recovery initiatives, and nutrition education.
White Street PizzaJonathan Williams
Jonathan Williams, a musician from Philadelphia with 15 years of experience, will be performing. He is known for delivering iconic hits from the past five decades. He has performed hundreds of shows at various venues, weddings, and private events throughout the Florida Keys and South Florida.
Two Friends Patio Restaurant & BarInformational Meeting for King & Queen of Fantasy...
If you are interested in becoming the King or Queen of Fantasy Fest 2026, attend this informational meeting to learn about the application process. Candidate applications are available at the Key West Campus, by downloading it, or by emailing Jennifer@fkspca.org.
FKSPCA Key WestVictoria Leigh
Victoria Leigh performs live at Sloppy Joe’s in Key West, offering high-energy island-inspired sounds and original mashups for a vibrant experience.
Sloppy Joe's BarSummer Bingo Night
Spend a lively summer evening at Key West Theater enjoying bingo with DJ Sanaris providing the soundtrack. Expect spirited games, upbeat music, prizes, and gift certificates for a cheerful night of entertainment.
Key West TheaterTbd
Enjoy live music at a local bar.
Tipsy Rooster Liquor Store and BarPatrick Garrity
Comedian Patrick Garrity began performing when he was young and has since become a seasoned road veteran. He lives on the road, touring the country continuously since 2010, and brings comedy shaped by constant travel.
Comedy Key WestBark & Brew
Oceans Edge Resort & Marina Key West and the Florida Keys SPCA are hosting Bark & Brew, a community event at Yellowfin Bar & Kitchen. Well-behaved dogs and their owners are welcome to enjoy an afternoon of relaxation, live music, waterfront views, happy hour specials, and a social atmosphere in Stock Island. There will be raffle prizes benefiting the Florida Keys SPCA. Food and beverages will be available for purchase, with raffle proceeds supporting local animal welfare efforts.
Oceans Edge Resort & Marina🧘 Meditation with Allen 🧘
Settle into stillness with Meditation with Allen, a calming session in the MCC Key West Sanctuary that offers a gentle pause in a welcoming setting. Open to everyone, it provides a quiet space for reflection, grounding, and renewal. Arrive as you are, breathe deeply, and take a moment to restore your focus.
MCC Key WestOne Piece TCG - Thursday Night League!
This weekly One Piece trading card game tournament awards a promo pack to every participant, and the player with the best overall record earns an exclusive winner pack.
The BIG Pride Fundraiser
The BIG Pride Fundraiser brings the community together at The Birdcage Cabaret for an evening centered on Pride, connection, and celebration. The gathering focuses on uplifting and inspiring attendees while uniting people around a shared vision for Key West. Special guest Senator Shevrin "Shev" Jones, a Florida State Senator and educator known as the first LGBTQ person elected to the Florida Senate, will take part. Recognized for consensus-building and a commitment to expanding pathways to opportunity for communities in Tallahassee, he brings that spirit to Key West. The event is hosted by Chris Massicotte, Chris for Key West.
The Birdcage CabaretFRLA Monroe Chapter - Meeting & Mixer
The FRLA Monroe Chapter hosts a meeting and mixer at Casa Marina Resort. The program begins with a board-only session, then transitions into a chapter meeting with presentations. Highlights include a keynote from Key West Mayor DeeDee Henriquez and a special presentation by Expedia Group. A networking reception follows the talks. Admission is $12 for FRLA members, $20 for a two-member discount, and $15 for non-member guests.
Plant Bingo in Marathon
Plant Bingo with the Florida Keys SPCA brings a relaxed evening where each game awards plants rather than cash, creating a lighthearted outing for plant lovers, bingo fans, and anyone interested in supporting animals. The event takes place at Courtyard by Marriott Faro Blanco Resort; check in at the Courtyard lobby and staff will guide you to the Coral Sands room. A $25 ticket includes five rounds of play plus a 25% discount on food and beverages from the on-site Bluewater Bar and Grill. Additional bingo cards are available for $5 each. Space is limited, so advance registration is recommended. Grow your collection with new greenery while backing the lifesaving work of the Florida Keys SPCA.
Courtyard by Marriott Faro Blanco ResortPokemon League
Meet other fans of the Pokémon Trading Card Game in a welcoming league environment. Use your own cards to enjoy casual matches, trade with fellow collectors, and aim for prizes while spending time with players who share your enthusiasm for Pokémon.
Game GridThursday Night Pokemon League
An event focused on Pokémon for fans to enjoy together.
Game GridKaraoke Nights
This summer brings a new twist as karaoke steps in for SINGO, hosted by Jacob Roman. All ages are welcome. For anyone seeking a little extra courage, $5 Green Tea Shots are available during karaoke. Feedback on the change is invited as the new format gets rolling.
Boondocks Grille and Draft HouseKiki's Live Music - John Andrews
Kiki’s Sandbar’s Thirsty Thursday features John Andrews performing smooth, island-inspired live music. Enjoy chilled drinks and tasty bites while taking in waterfront views and that easygoing Keys vibe. A welcoming mix of good food, refreshing sips, and mellow tunes creates a simple way to unwind.
Kiki's Sandbar & GrilleWicked Bingo
Back for another round, this music trivia bingo night challenges players to recognize artists and song titles from curated sets of songs. Correct identifications can lead to rewards selected by a wheel of prizes.
The Retro RoomTaking Back Thursday's!
22&Co and Joe present a nostalgic celebration inspired by 2001, creating a playful party atmosphere with early-2000s energy.
Yoga for All
Located next to the beach volleyball courts beneath a large shade tree, this session meets in a shaded outdoor setting. Mats are available to borrow, and it operates on a donation basis.
Sombrero Beach Marathon, FLSummer Reading: Monroe County Sheriff's Animal Farm
Animals from the Monroe County Sheriff's Animal Farm will visit the Big Pine Library for an educational program. Attendees can discover what makes each creature unique and meet the farm’s furry residents. This event is part of Summer Reading and is open to everyone.
Big Pine Key LibraryTruman Waterfront Farmers Market
A weekly open-air market brings a friendly buzz to Truman Waterfront Park in Key West. It continues throughout the year.
Truman Waterfront ParkRock -n- Read Summer Reading
The American Society for the Prevention of Cruelty to Animals visits the Marathon Library Branch to introduce some animals and share information about its mission in the Florida Keys. Children can browse and select books to record in their Summer Reading logs, giving them additional chances to win prizes.
Marathon LibraryTruman Waterfront Market Key West
An open-air community market where area farmers, food vendors, artists, and artisans come together, offering fresh produce, a variety of foods, and handcrafted goods.
Truman Waterfront ParkJoe the Show
Joe the Show brings a performance to Rick's Bar in Key West.
Rick's BarFlorida Keys PBA Dolphin Tournament
This is a competitive offshore fishing tournament. Anglers come together for two days of fishing, weigh-ins, and friendly competition. Cash prizes are awarded to the top anglers, including categories for junior, female, and PBA members. The event benefits the Autism Society of the Keys and The Love Fund, Inc., which support community initiatives throughout the Florida Keys.
Oceans Edge Resort & MarinaHanks
Nick Norman appears at Hank’s in Key West, Florida.
Hank's Hair Of The Dog SaloonGator’s at Geiger Key
A live performance by The Gator Nate takes place at Geiger Key in Key West. On site overnight rentals are available.
Mamey & Mojitos Ice Cream Social
This Conch-style ice cream social at the Alex Vega Key West Firehouse Museum honors 115 years of the historic mamey tree. Guests can enjoy freshly made mamey ice cream and cool off with mojitos prepared with Key West’s First Legal Rum and fresh mint. Author Ernesto Vildostegui will be on hand to celebrate the release of his new book, The Life We Had At The End of the Road. Music is provided by DJ Arson, and a Bolita number drawing is planned. Admission to the museum is free. Friends and family are welcome to experience a Key West tradition.
Alex Vega Key West Firehouse MuseumKIKI'S LIVE MUSIC- DJ KHAOTIC
DJ Khaotic brings a live set to Kiki’s Sandbar, filling the space with upbeat music, dancing, and relaxed island vibes. Expect a steady flow of crowd favorites and fresh beats that keep the energy high and the dance floor moving.
Kiki's Sandbar & GrilleFollow The Rabbit... (6PM)
Follow The Rabbit Bar presents an immersive, speakeasy style show in the Back Stage Listening Room at Key West Theater. Step into a Wonderland themed setting for two hours of spontaneous entertainment that blends burlesque, dance, circus artistry, and vivid light performances. Creative cocktails and mocktails are part of the experience, with performers serving drinks one moment and surprising the room with live acts the next. This event is for ages 21 and over. Tickets include a password that grants access to this intimate show.
Key West TheaterFabulous Spectrelles
Enjoy a lively salute to classic Motown and doo-wop as The Fabulous Spectrelles deliver tight harmonies, choreography, and favorites from the 1950s and 1960s. Recognized as Key West’s longest running musical revue, the group has entertained audiences for more than 43 years. The show is now in residence at KAYA Key West EmPOURium, with performances in the Karaoke Lounge at The Key West EmPOURium.
Kaya Island EatsTea & Poetry | DONATION-BASED with Bliss
Tea and Poetry is a donation-based gathering co-led by Bliss and Taylor that offers a quiet refuge for presence, connection, and creative expression. Through shared tea, original poetry, spoken word, and open-hearted listening, participants shape a ceremonial open mic where stories, songs, prayers, and even silence are welcome. The focus is to open the heart, let go of what does not serve, and reconnect with authentic essence while inviting creativity and intuition to guide the experience. Every voice is honored, and the simple act of being seen and heard is held as part of the healing. Contributions are pay what you desire, and presence is the only requirement.
Early Bird Clean Up Higgs Beach
This community cleanup focuses on White Street, Atlantic Boulevard, and Higgs Beach in preparation for the 250th Fourth of July celebration. Participants will remove litter and freshen up these areas so they are ready for the festivities. Look for the green neon trailer in the parking lot by the Bocce courts to check in and pick up provided buckets, vests, and pickers. Those who are new to plogging should plan to arrive a little early and bring a valid ID to complete City of Key West paperwork. Even a single hour of participation can make a big difference.
Key West Wildlife Center & Indigenous ParkKaraoke Night
At Boardwalk Bar & Grill in Big Pine Key, karaoke takes center stage with Nick and drink specials. Attendees can step up to the mic and sing their favorite songs in a lively setting.
Boardwalk Bar & GrillJoe the Show & His Wheel of Musical Destiny
Joe the Show turns the night into a spin-powered soundtrack as a wheel decides what plays next. The outcome might be Taylor Swift singalongs, a burst of 80s hits, possible freebies like tots and shots, and the kind of choices that make for next-day stories, sometimes all in a single go. Expect a lively, anything-can-happen vibe at Mary Ellen’s, with surprises revealed on every spin.
Mary Ellen's Bar & KitchenFollow The Rabbit... (9PM)
Follow The Rabbit Bar presents an immersive speakeasy-style show in the Back Stage Listening Room at Key West Theater. Over two hours, surprise pop-up moments blend burlesque, dance, circus artistry, and playful light displays with creative cocktails and mocktails. Performers serve specialty drinks, then pivot into high-energy numbers, keeping the room full of unexpected turns. A password is provided for this intimate Wonderland-inspired experience. Guests must be 21 and over.
Key West TheaterDJ Sanaris Rocks Tiki House!
DJ Sanaris brings a lively dance party to Tiki House Key West, spinning crowd-pleasing hits to keep the floor moving. A high-energy soundtrack sets the tone for a fun night of dancing.
Tiki HouseAndy Westcott
Rams Head Southernmost welcomes Andy Westcott for an event.
Rams Head SouthernmostJonathan Williams at Pier House Resort & Spa on Friday, Jun 26, 2026
Philadelphia native Jonathan Williams, now based in Key West, performs at the Caribbean Spa at Pier House Resort. A versatile musician with nearly 15 years of experience, he offers a set of iconic hits that spans five decades.
Caribbean Spa at Pier House ResortEric Culberson
Eric Culberson makes a much-anticipated comeback to Green Parrot Bar with three extended sets, each about ninety minutes. This engagement is part of an entire weekend of lively performances at the venue.
Green Parrot BarPatrick Garrity
Patrick Garritys Never Ending tour continues! For over 20 years, Garrity has toured the country building a following with his witty takes on current events, hardships, and ironies. He performs solo or with other talented comedians, offering comedy entertainment that audiences enjoy.
Comedy Key WestKaraoke w/ Jason on Saturday, Jun 27, 2026
Enjoy karaoke with Jason at Rick's Bar.
Rick's BarFord and Friends Dinner
Salt + Ash hosts a one night collaboration as Chef Jeremy Ford and Chef Kyle Campbell team up with guest chefs Paula DaSilva and Carissa DaSilva. A five course menu highlights produce from Ford’s Farm alongside local seafood, with each course shaped by the combined creativity of all four chefs. The result is an intimate, chef driven experience that places fresh ingredients and thoughtful technique at the center of the table.
Salt + AshKiki's Live Music
Kiki’s Sandbar hosts the Pierce August Band for a live performance loaded with high-energy country and Americana favorites. Dance with your toes in the sand, enjoy cold drinks, and take in an upbeat atmosphere throughout the show.
Kiki's Sandbar & GrilleFGHC Fishing Charter
Enjoy a six hour fishing charter with a welcoming group of women, aimed at reaching catch limits and taking a shot at trophy catches. The $400 fee includes fishing licenses, rods and reels, bait, tackle, fuel, food, and drinks for a low stress day on the water. Expect friendly company, memorable fishing, and the chance to head back with a well stocked cooler. Space is limited and spots are available.
Coco Plum BeachMonthly Community Yard Sale
Browse bargains and hidden treasures at a community yard sale hosted at the MARC Plant Store. Sellers can book a vendor space with a $15 donation, and advance reservations are required. To reserve, call the store or drop in to sign up. Shop, sell, and lend support to the local community.
MARC Plant StoreMango Fest
Mango Fest returns to Bayview Park in Key West with a one-day celebration of the island’s mango season. The festival features mango-inspired bites paired with tropical flavors and island-style food and drinks. Local artists and makers showcase handmade creations while live music fills the park with an easy Key West groove. The experience is family friendly and highlights sunshine, good food, and the community spirit that defines tropical life in Key West.
Bayview ParkJazz Brunch
After a strong kickoff last weekend, the Jazz Brunch Series returns to Conchiglia with live music by The Hoagy’s featuring Claire Caplan, Larry Smith, and Skipper Kripitz. Enjoy handcrafted brunch cocktails, Italian brunch favorites, wood fired pizza, and fresh pasta in a tropical garden setting. Reservations are recommended.
ConchigliaJeff Clark
Enjoy a live appearance by Jeff Clark at Schooner Wharf Bar & Grill.
Schooner Wharf BarAmerica Celebrates 250 Years
Key West marks the nation’s 250th anniversary with a lively parade along Duval Street that concludes with a community celebration at the Truman Waterfront. Leading up to the festivities, the county is encouraging businesses on U.S. 1 to display American flags, with community partners bringing out giant flags so travelers see plenty of red, white, and blue, and to keep them flying through Flag Week. The county also highlights the strong tradition of early July celebrations hosted by local rotaries and chambers across the Keys, with continued support from Key West International Airport.
Duval StreetPatrick Garrity
Patrick Garrity performs live at Comedy Key West.
Comedy Key WestFarm Open House
The farm welcomes public visitors with free entry. Donations are always appreciated.
Monroe County Sheriff's Office Animal FarmTarot & Tea | DONATION-BASED with Jolie
At Evolve Key West Temple, a donation-based gathering with Jolie blends tarot exploration with a calming tea ritual. The atmosphere is warm and supportive, creating space for intuition to unfold and meaningful insight to emerge. Expect guidance that reflects your current path, a deeper connection with inner wisdom, heartfelt sharing in a respectful circle, and the soothing rhythm of tea to ground and open the spirit. Suitable for all experience levels, with an emphasis on curiosity and an open heart.
Evolve Key WestJack Fivecoate
Reggae Sundays at Kiki’s Sandbar features Jack Fivecoate performing a mix of reggae favorites alongside his own original songs. Move to the rhythm in the sand while enjoying a drink and an easygoing vibe.
Kiki's Sandbar & GrilleCutting Energetic Cords: Release & Let Go | DONATION-BASED with Debbi
This donation-based ceremony offers a gentle space for energetic release and renewal. In a quiet, nurturing setting touched by lunar light, participants are supported in letting go of emotional attachments, outgrown relationship patterns, and energetic imprints that have run their course. The experience weaves guided visualizations, intentional breathing, and meditative ritual to bring awareness to the subtle cords that keep energy tied to the past. With compassion and clear intention rather than force, these bonds soften and unwind so what once felt heavy becomes light, what was bound grows free, and what is ready transforms into wisdom. As layers clear, a steadier sense of clarity, personal sovereignty, and inner peace emerges. It can be especially supportive during times of transition, for emotional healing, for setting healthy boundaries, or when beginning a new chapter with greater alignment and space. Arrive as you are, and step away feeling lighter, clearer, and more deeply connected to yourself.
Evolve Key West80s & 90s Trivia Night!
Rediscover the 80s and 90s at a live team trivia night at the Retro Room. Pop culture questions from both decades set the stage as teams of up to six players compete for prizes. Held every Sunday, it is a chance to team up, test your recall, and enjoy some friendly competition.
The Retro RoomQueens of Havana
Experience a lively Key West brunch where drag performances by the water meet Cuban-inspired style, creating a bold celebration in the middle of the day.
Flama CabanaJeff Clark
Enjoy an appearance from Jeff Clark at Schooner Wharf Bar & Grill.
Schooner Wharf BarSummer with the Symphony
South Florida Symphony presents its chamber music series in Key West with a candlelit performance that offers a cool respite on a summer afternoon. The concert features music by Farrenc and Pejačević in an intimate setting that invites close listening.
Tennessee Williams TheatreKiki's Live Music
Gary Hempsey brings a live performance to Kiki's Sandbar Bar & Grille in a waterside setting as the sun sets. Cold drinks and an easygoing atmosphere accompany the music.
Kiki's Sandbar & GrilleClass: Fused Glass Art Open Workshop
Explore the art of fused glass in a fast paced introductory class focused on creating wall art. Beginners will learn essential techniques, while experienced participants have access to equipment and basic glass. The session covers cutting, preparing pieces for the kiln, and firing. Each person can work within an 8x8 area, with finished pieces ready for pickup the following week. Choose from a wide range of colors and design templates, or create your own. All materials are included. Specialty glass and add ons for items such as key rings, wine bottle stoppers, and jewelry are available for purchase. Class size is limited to 6. The fee is $75. Only paid registrations are guaranteed a seat. Bring reading glasses if you need them.
SuzDesign StudioJay Klein
Jay Klein performs a live music set at Schooner Wharf Bar & Grill.
Schooner Wharf BarTrivia Night Mondays at Key West Cooking Show
Challenge both your mind and your palate at Trivia Night at the Key West Cooking School. This lively gathering blends food-focused fun with friendly competition as teams take on trivia in a welcoming setting.
Key West Cooking ShowCharles Miller
Enjoy an appearance by Charles Miller at Rick's Bar in Key West.
Rick's BarKey Lime Festival
Set in Key West, Florida, and hosted at First Flight Island Restaurant & Brewery, this five-day Key Lime Festival is promoted as America's favorite celebration of citrus. It blends citrus, creative moments, and the island's freewheeling spirit to create a distinctive experience.
First Flight Island Restaurant & BreweryClass: Fused Glass Art Open Workshop (Big Pine)
Explore fused glass in a lively, hands-on workshop where beginners create a piece of wall art while learning essential techniques. More experienced participants can make full use of the studio’s tools and basic glass. Instruction covers cutting, preparing projects for the kiln, and the firing process. Each person designs within an 8-by-8 inch space and can include as many pieces as will fit, with finished work available for pickup the following week. Choose from a wide range of colors and design templates, or craft an original idea. All standard materials are provided, and specialty glass plus add-ons like key rings, wine bottle stoppers, and jewelry components are available for purchase. Class size is limited to six. The cost is $75, and seats are guaranteed once payment is received. Bring reading glasses if helpful. To register, contact the organizer directly.
Big Pine Key, FloridaNick Brownwell
Schooner Wharf Bar & Grill presents a performance by Nick Brownwell. Settle in and enjoy the show.
Schooner Wharf BarJimmy Buffett Tribute Show
A live lunchtime tribute to Jimmy Buffett takes the stage at Comedy Key West in central Key West. This mid-day performance celebrates his music onstage. Reservations are recommended.
Comedy Key WestJesse Lee
Part of the Key West live music schedule, this event appears alongside listings for festivals and events, happy hour specials, and the area’s bars and saloons. It is included within a broader guide to Key West that also features casual restaurants, boat rentals, campgrounds and RV parks, and deep sea fishing.
Rick's BarTransformational Breathwork — KeysTix.com
This free session uses conscious breathing techniques to help you move stagnant energy. The goal is to integrate emotional and physical experiences to facilitate healing and personal growth. You will be guided through the process of releasing tension, resetting your nervous system, and reconnecting with yourself.
Queer Keys Community CenterFLO-RAW
FLO-RAW performs live at Sloppy Joe's Bar in Key West. Tickets are available for this show.
Sloppy Joe's BarThe Key Lime Festival Kick Off Party
At The Avalon, the Key Lime Festival opens with live music, tropical cocktails, and plenty of lime-themed fun. A welcome keynote by festival co-founder, historian, and cookbook author David L. Sloan sets the tone, with festival merchandise on hand and a full cash bar. The celebration features the second annual Key Lime SPIRIT Pageant, where contestants compete for the titles of Key Lime Festival Emperor and Empress in a high-energy showcase of personality, creativity, and Key West flair. Admission is free. To enter the pageant, email aandrade@southernmostresorts.com.
The AvalonCafe Sole Key Lime Inspired Menu
Cafe Sole is featuring a Key Lime inspired menu that celebrates bright, citrusy flavors. Build a three course experience by selecting one appetizer, one entree, and one dessert, and receive $10 off the set. A glass of Sancerre is suggested as a pairing. Appetizer options include Ultimate Conch Salad, with thin slices of conch lightly dressed in key lime and olive oil, plus a touch of Asiago, red bell pepper, Bermuda onion, and capers. Another choice features gruyere cheese puffs filled with grilled local pink shrimp and finished with a beurre blanc made from shallots, Sancerre, key lime, and butter. For entrees, Key Lime Hogfish is pan seared and served with a handmade hollandaise infused with key lime and roasted red peppers. There is also pistachio crusted ahi tuna accompanied by a light wasabi cream lifted with key lime. Desserts continue the theme. Key Lime Zabayon blends key lime juice with white wine and eggs into a warm, whipped custard. Key Lime Pie offers a cream cheese mousse flavored with fresh key limes and topped with house made marshmallow and Chantilly cream. The full regular menu is available as well. Reservations are recommended.
Cafe SoleKey Lime Tiramisu & Key Limecello!
At Better Than Sex, savor Key Lime Tiramisu with Key Limecello in a romantic setting lit by candlelight, created for memorable moments and sweet indulgence.
Better Than Sex - A Dessert RestaurantSummer Bingo Night
Enjoy a lively bingo night at Key West Theater with DJ Sanaris keeping the energy up between rounds. Expect games paired with music, fun giveaways including gift certificates, and a comfortably air conditioned setting. Entry is free, bingo cards cost $5, and a two drink minimum applies. Attendees must be 21 or older.
Key West TheaterBusiness Before Hours
Connect with business leaders from Key West and nearby communities at a before-work networking gathering held at the Greater Key West Chamber of Commerce. Everyone is welcome to attend, and Chamber membership is not required. It is a helpful way for those considering membership to get a feel for the Chamber community. This event is sponsored by First State Bank. Registration is available.
Greater Key West Chamber of CommerceThe Key Lime Festival 2026
Celebrate the flavors and quirks of the Florida Keys at a lively tribute to citrus, community, and the pie that put this island on the map. Set in Key West, Florida, this multiday festival features five days of culinary experiences for every palate, including returning highlights like the Key Lime Cocktail Sip & Stroll and the Key Lime Pie Hop, along with new additions for devoted key lime fans. Expect playful, offbeat fun and plenty of chances to savor the signature dessert where it all began. Ticket information is coming soon, and updates will be shared on social media.
The Key Lime FestivalKey Lime Rum Tasting
Explore the craft of rum at Key West First Legal Rum Distillery with tours that let you see the distilling process up close. Enjoy complimentary tastings of rums and other spirits, including key lime rum. It is a welcoming way to learn, sample, and experience craft distilling in one visit.
Key West First Legal Rum DistilleryDJ Todd at Rick's Bar Key West on Wednesday, Jul 1, 2026
Rick's Bar in Key West hosts DJ Todd for a live DJ performance.
Rick's BarFLO-RAW
FLO-RAW appears at Sloppy Joe's in Key West for a ticketed event.
Sloppy Joe's BarSloppy Joe's Ultimate Key Lime Pie Smash Party
At Sloppy Joe’s Bar, a lighthearted fundraiser turns Key Lime pies into hilarious splats for a good cause. Donate and vote to choose which local notables and Sloppy Joe’s staffers get pied, with contributions benefiting The Sloppy Joe’s Foundation. Admission is free.
Sloppy Joe'sClass: Fused Glass Art Open Workshop (Big Pine)
Explore the art of glass fusing in a fast paced introduction where beginners create fused glass wall art while learning cutting, kiln preparation, and firing. Glass fusing joins multiple pieces of glass in a kiln using heat. Advanced students have access to all studio equipment and basic glass. Specialty glass and accessories for key rings, wine bottle stoppers, and jewelry are available for purchase. Each participant can work within an 8 by 8 area and include as many pieces as will fit, with finished work available for pickup the following week. Choose from many design options and colors or design your own, and all standard materials are included. The fee is $75, and the session is limited to 6 students. Seats are guaranteed only for paid registrations. If you use reading glasses, bring them. To sign up, contact the organizer directly.
Big Pine Key, FloridaMinions and Monsters
In 1920s Hollywood, the Minions hunt for real terrors to fuel a monster movie, team up with a mysterious green creature, and then race to save the world after the monsters they unleash spiral out of control. What begins as a search for cinematic thrills turns into a planet-sized predicament. Rated PG, running 1 hour and 30 minutes.
Marathon Community CinemaA Pirate Looks Back: Jimmy Buffett Tribute Show
Experience a lunchtime tribute to the music of Jimmy Buffett, performed live at Comedy Key West in the heart of Key West. Reservations are recommended.
Comedy Key WestTruman Waterfront Market Key West
At the Truman Waterfront Farmers Market, local farmers, culinary vendors, artists, and makers gather in an outdoor community setting. Explore their offerings and connect with the people behind the work in a welcoming, open-air atmosphere.
Truman Waterfront ParkTBA at Rick's Bar Key West on Thursday, Jul 2, 2026
Rick's Bar in Key West is set for live music, with details to be announced. This listing connects to the wider calendar of local festivals and events within the area’s bars and saloons.
Rick's BarJuly 4th Festivities
A seaside Fourth of July sets an inviting tone that feels like a gateway to paradise. This coastal-themed celebration captures the spirit of the sea for a holiday escape.
The Reach Key West, Curio Collection by HiltonKey Lime Sip & Stroll
This Key Lime cocktail stroll invites participants to check in at First Flight Island Restaurant & Brewery, then visit participating bars as they compete for the top Key Lime drink on the island. Guests can sample everything from classic margaritas to inventive specialty cocktails and cast a vote for their favorite. The cost is $55 per person and includes cocktail samples at multiple locations.
First Flight Island Restaurant & BreweryOceanfront Weekend Brunch at Four Marlins
Weekend brunch at Four Marlins brings coastal-inspired cuisine together with beautiful water views in Key West. Choose an oceanfront patio table or settle into a comfortable indoor spot while live music sets a laid-back tone. The atmosphere is relaxed and unhurried, making it easy to savor the experience at your own pace.
Four Marlins Oceanfront Dining5-Alarm Pie Challenge
At The Alex Vega Key West Firehouse Museum, visitors can sample a complimentary spicy take on Key lime pie created by cookbook author David L. Sloan, featuring a cayenne-spiced graham crust, habanero cream, and a jalapeño garnish. The museum highlights both its historic roots and haunted lore, with a smartphone-accessible audio tour that explores haunted history alongside the legacy of firefighting in Key West. Guests can also view the family flag of former festival founder David Sloan, created for the 1876 centennial. Admission is free, and donations help support the museum.
The Alex Vega Key West Firehouse MuseumViva's Key Lime Brunch
Viva Argentine Steakhouse presents a Key Lime themed brunch filled with tropical tastes, a relaxed island vibe, and limited-time food and drink specials. The kitchen adds its own twist to a beloved citrus, bringing bright, zesty flavors to the menu. Enjoy good food with friends and a little extra zing, with brunch-only specials available while the event is underway.
Viva Argentine SteakhouseFLO-RAW at Sloppy Joes Key West
FLO-RAW, recognized as Best of the Bay's Best Pop Band, returns to the historic Sloppy Joes Key West with a high-energy performance that spans genres and decades.
Sloppy Joe's Bar3rd of July Cookout at the Harry S. Truman Little White House
A free, family-friendly cookout on the lawn of the Truman Little White House in Key West celebrates America’s 250th, with BBQ, a cash bar, and patriotic activities. Red, white, and blue attire is encouraged.
Truman Little White HouseRicky Cruz at Comedy Key West
A comedy lineup includes the Key West Comedy Competition and a separate show featuring Tom Arnold. One evening centers on a competition format, while another highlights a single performer for a night of laughs.
Comedy Key WestFLO-RAW
FLO-RAW will perform live at Sloppy Joe's Bar in Key West. This is a ticketed event.
Sloppy Joe's BarJuly 4th Star Spangled Fireworks Cruises
Celebrate Key West’s Star Spangled Spectacular from the water aboard modern vessels, with cruises offering sweeping views of fireworks over the Atlantic. Skip the crowds and watch the show unfold from an on-the-water vantage point.
Sunset Watersports Key WestSplish, Splash & Sparkle!
Celebrate Independence Day at Morning Joint with the Florida Keys SPCA during a playful gathering that welcomes both people and pups. Dogs can cool off in splash pads and pools, enjoy pup cups, and pop bacon-scented bubbles. Kids can take on a water balloon toss, with the winner earning free ice cream from Morning Joint’s Ice Stream. Pick up retro sparklers to keep the festivities going later. Themed professional photos with children or pets are available for a suggested $20 donation, provided by Photo Design by Natalie.
Morning JointRotary Club of Key West 4th of July 5K Run/Walk
This annual Key West tradition features a scenic 5K run and walk at Edward B. Knight Pier, hosted by the Rotary Club of Key West. Proceeds benefit the Edward B. Knight Scholarship Fund, supporting vocational students in Monroe County. Registration is $30 for children 12 and under, with adult rates ranging from $45 to $50 depending on the registration period. Every participant receives a race T-shirt and a commemorative metal.
White Street Pier4th of July Fireworks Watch Party
A festive evening on the water blends Key West highlights into one seamless experience. It begins with cocktails and hand-passed small bites while taking in the famous sunset, then continues with a leisurely sail along the island's south side before anchoring near White Street Pier to watch fireworks shimmer over the sea. The outing takes place aboard S/V Argo Navis, the sole 75-foot luxury catamaran yacht in Key West. Expect chef-prepared small plates, tray-passed appetizers, sweet bites, and signature cocktails, plus a selection of premium wines, craft beer, straightforward cocktails, mocktails, and other nonalcoholic options. The price is $219 per person.
S/V Argo NavisMarathon Rotary 4th of July Parade and Picnic
Mark America’s 250-year anniversary with a beachside celebration that starts with a patriotic parade traveling from Marathon High School to Sombrero Beach. After the procession, the party continues on the sand with hot dogs, hamburgers, a cornhole tournament, live music, kids’ games, and more. The City of Marathon caps the day with a fireworks show accompanied by patriotic music on US1 Radio 104.1. Boaters are encouraged to watch from the beach or just offshore of Sombrero Beach. Admission is free.
Sombrero Beach4th of July Allstars at 5:30, 9:00 & 11:00 at Green Parrot Bar on Saturday, Jul 4, 2026
An extended program unfolds across three consecutive sets, each lasting 90 minutes, offering a sustained experience from the opening to the close.
Green Parrot BarMichael Corelto at Rick's Bar Key West on Saturday, Jul 4, 2026
Live music fills Rick's Bar in Key West when Michael Corelto performs.
Rick's Bar2026 Key Lime Pie Drop
At the Key West Lighthouse, teams and tinkerers put their creativity to the test by dropping a Key Lime Pie from the top and trying to keep it intact. Expect clever contraptions, surprising splats, and a spirited dose of pie-fueled chaos. It is free to attend, and competitors may enter at no cost, but registration is required. Only one entry is allowed per team or contraption. Teams can include up to four people, and costumes are encouraged. Prizes include a cash award and trophy for first place, along with honors for most creative design, best splat, and best Key Lime theme. Devices must follow the rules: no motors, weights, rocks, metal, slime, or other goo; nothing can be permanently attached to the pie; parachutes are permitted; the container must be in free fall with no bungees or tethers; and it must weigh no more than three pounds. Balloons are strongly discouraged.
Key West LighthouseKey West Artisan Market
This vibrant open-air marketplace highlights local artists, makers, and food vendors in a laid-back island setting. Browse handcrafted items and original artwork as you explore the Key West Artisan Market and enjoy the easygoing atmosphere.
Clarence S.Higgs Memorial BeachHarley Ray at Rick's Bar Key West on Sunday, Jul 5, 2026
Harley Ray appears at Rick's Bar in Key West.
Rick's BarKaraoke w/ Chris at Rick's Bar Key West on Monday, Jul 6, 2026
Live Music Schedule Festivals & Events Happy Hour Specials Bars & Saloons Bed & Breakfast - Key West Boat Rentals | Key West Campgrounds & RV Parks Casual Restaurants Deep Sea Fishing Dry Tortuga...
Rick's BarSPANISH 1: BEGINNERS LEVEL WITH SARAH ANFINSON
Build a foundation in Spanish with a three-week beginner course that gets you speaking simple, practical phrases from day one. Guided by Sarah Anfinson, a high school Spanish teacher with 30 years of experience, you will explore essential vocabulary, pronunciation, and everyday expressions at a comfortable pace. This level is designed for learners with little or no prior experience. Classes meet on Mondays and Wednesdays. A student workbook is included in the price, and participants are asked to bring a notebook and pencil. Workshop price: $150.
Williams HallSPANISH 2: INTERMEDIATE LEVEL WITH SARAH ANFINSON
Designed for learners with a basic foundation in Spanish, this three week class refreshes core skills and moves into everyday conversation. Taught by Sarah Anfinson, a high school Spanish teacher with 30 years of experience, it expands on material from level 1. A student workbook is included in the price, and participants should bring a notebook and pencil. The workshop price is $150.
Williams HallFLO-RAW at Sloppy Joes Key West
Recognized by Best of the Bay as Best Pop Band, FLO-RAW returns to the historic Sloppy Joe's Bar with a high-energy performance that blends music from many genres and decades.
Sloppy Joe's BarFLO-RAW at Sloppy Joes Key West
FLO-RAW, recognized by Best of the Bay as Best Pop Band, returns to the historic Sloppy Joe's Key West with a high-energy performance that blends music across genres and decades.
Sloppy Joe's BarJesse Lee at Rick's Bar Key West on Tuesday, Jul 7, 2026
Jesse Lee takes the stage at Rick's Bar in Key West for a live performance.
Rick's BarCarson Lowe at Rick's Bar Key West on Wednesday, Jul 8, 2026
Carson Lowe takes the stage at Rick's Bar for a performance.
Rick's BarSummer Reading: Ranger Katy at the big Pine Library
Ranger Katy from the National Key Deer Refuge returns to the Big Pine Library for a Summer Reading program. Explore the natural world just beyond your window, then wrap up with an interactive activity. Everyone is welcome.
Big Pine Key LibraryA Pirate Looks Back: Jimmy Buffett Tribute Show
Comedy Key West presents a lunchtime tribute to Jimmy Buffett performed live on stage in central Key West. This midday show makes it easy to work a bit of live entertainment into the day. Reservations are recommended.
Comedy Key WestJoe the Show at Rick's Bar Key West on Friday, Jul 10, 2026
Joe the Show performs at Rick's Bar in Key West.
Rick's BarKaraoke w/ Jason at Rick's Bar Key West on Saturday, Jul 11, 2026
Jason hosts karaoke at Rick's Bar, featuring a lively, casual atmosphere with the spotlight on the crowd.
Rick's BarDel Brown Invitational Permit Tournament
Leading anglers and their guides converge in Sugarloaf Key, Florida for the Del Brown Invitational Permit Tournament, a fly fishing competition focused on permit. Competitors vie for top honors in the longest standing permit fly fishing tournament worldwide.
South of the SevenJust George at Rick's Bar Key West on Monday, Jul 13, 2026
Rick's Bar in Key West hosts Just George.
Rick's BarTrivia Night Mondays at Key West Cooking Show
Put your knowledge and your taste buds to the test at a lively trivia night at the Key West Cooking School. Enjoy food, plenty of fun, and friendly competition as participants answer questions throughout the evening.
Key West Cooking ShowComedy Key West Open Mic
Key West’s lone open mic brings together comedy, music, variety, and a hint of impropriety in a welcoming showcase. The stage welcomes performers of every kind, from stand-up comics and musicians to poets and people who may not yet realize they are performers.
Comedy Key WestPlant Bingo in Big Pine!
At Pop’s Smoke Shed, a relaxed plant-themed bingo night replaces cash payouts with plant prizes. It welcomes plant lovers and bingo fans alike while supporting the lifesaving work of the Florida Keys SPCA. Each $25 ticket covers five rounds, and extra bingo cards are available for $5 each. Space is limited, so advance registration is recommended. Spend an easygoing evening, try your luck at growing your collection, and contribute to animal care through the Florida Keys SPCA.
Pop's Smoke ShedLive at Margaritaville Key West
A three-hour live performance unfolds at Margaritaville Restaurant in Key West, delivering a continuous set from start to finish.
Margaritaville RestaurantLive at Margaritaville Key West
A three-hour set takes place at Margaritaville Key West.
Margaritaville RestaurantEarly Bird Clean Up
Roll up your sleeves for a quick neighborhood spruce-up on Lower Duval. Organized by Irish Kevin's and the Key West Military Affairs Committee, volunteers will meet behind Irish Kevin's at the green neon trailer in the parking lot to pick up buckets, safety vests, and litter pickers before heading out to clean the area for Hemingway Days. Just one hour of effort can make a meaningful difference.
Irish KevinsSummer Reading: Mosquito Control visits the Big Pine Library
Learn what goes into mosquito control when Mosquito Control is at the Big Pine Library. Explore facts about these flying insects and examine specimens through microscopes. This program is part of Summer Reading and is open to everyone.
Big Pine Key LibraryJonathan Williams at Schooner Wharf Bar & Grill on Friday, Jul 17, 2026
Philadelphia-born Jonathan Williams is a versatile, Key West based musician with nearly 15 years of experience who performs iconic hits that cover five decades. Audiences can look forward to a broad mix of well known songs from across the years.
Schooner Wharf BarLive at Margaritaville Key West
Experience a three hour set at Margaritaville Key West.
Hemingway Days & Hemingway Look-Alike Contest
Key West hosts a lively five-day celebration of Ernest “Papa” Hemingway, honoring his life, legacy, and time on the island. The festivities combine literary tributes with a playful spirit. The Hemingway Look-Alike Contest takes place at Sloppy Joe’s Bar.
Sloppy Joe's BarBusiness After Hours
Connect with fellow professionals at a casual, monthly Greater Key West Chamber of Commerce networking gathering. Typically 50 to 75 member business professionals take part, creating easy opportunities to make connections, exchange ideas, and talk business in a relaxed social setting. This edition is hosted at Key West Cooking Show. Admission is $10 for Chamber members and $20 for non members. Each month a different Chamber business showcases its workplace as host, providing food, beverages, and at least one door prize, while the Chamber spreads the word through its media channels.
Key West Cooking ShowFish Out of Water - Live in Marathon, FL!
Fish Out of Water brings the Can't Stop, Won't Stop Tour to Dockside Boot Key Harbor for a live set in Marathon Key. The performance blends rock, funk, reggae and hip hop with acoustic elements, highlighting the band's RoPhunkRaeHop style.
Dockside Boot Key HarborFish Out of Water - Brunch in Key West, FL!
Fish Out of Water brings its Can't Stop, Won't Stop Tour to Blue Heaven for a live brunch set in Key West. The performance features a blend of rock, funk, reggae, and hip hop with acoustic elements.
Blue HeavenSummer Reading: Bahia Honda State Park
Meet the rangers who make the state park a fun place for adventure as they share insights about its waters, plant life, and the animals that live in the park.
Big Pine Key LibraryJust George at Rick's Bar Key West on Monday, Jul 20, 2026
A live music performance in a classic Key West bar and saloon setting, part of the area’s mix of festivals and events. The wider Key West scene includes casual restaurants, boat rentals, deep sea fishing, and access to the Dry Tortugas, along with lodging choices that range from bed and breakfasts to campgrounds and RV parks.
Rick's BarTrivia Night Mondays at Key West Cooking Show
Participants challenge both their knowledge and their taste buds at a trivia night presented by the Key West Cooking School. The event brings together food and a team-based contest for a culinary twist on classic trivia.
Key West Cooking ShowSloppy Joe’s Annual Hemingway Days
A playful celebration in Key West honors Ernest “Papa” Hemingway with a hallmark tribute to one of literature’s greats. The tone is light and imaginative, offering an affectionate salute to his enduring legacy.
Sloppy Joe's BarFish Out of Water - Brunch in Key West, FL!
Fish Out of Water brings the Can't Stop, Won't Stop Tour to Blue Heaven for a live brunch set in Key West, Florida. The performance blends rock, funk, reggae, hip hop, and acoustic sounds, featuring their signature RoPhunkRaeHop style.
Blue HeavenComedy Key West Open Mic
Described as Key West's only open mic for comedy, music, variety, and a bit of impropriety, this night at Comedy Key West welcomes performers of every stripe, from comedians and musicians to poets and people who are brand new to the mic.
Comedy Key WestKey West Marlin Tournament (2026)
The Key West Marlin Tournament features high-level sportfishing in the Florida Keys, bringing together spirited competition, opportunities for cash awards, and memorable adventures on the ocean. Participants can expect action on the water and a setting that highlights the thrill of the catch.
DoubleTree Resort by Hilton Hotel Grand Key - Key WestItalian Heritage Wine Dinner
At The Rhum House, a five course Italian wine dinner pairs each course with wines from celebrated regions including Tuscany and Sicily. The menu centers on seasonal ingredients, classic Italian techniques, and a contemporary presentation. Each pairing is curated to amplify the character of both dish and glass, creating a flavorful tour of Italy over the course of the evening. Seating is limited, and reservations are required.
The Rhum HouseJoe the Show at Rick's Bar Key West on Thursday, Jul 23, 2026
Joe the Show performs at Rick's Bar in Key West.
Rick's BarKaraoke w/ Jason at Rick's Bar Key West on Friday, Jul 24, 2026
Karaoke with Jason takes place at Rick's Bar in Key West. It is part of the local live music and festivals and events scene among the area's bars and saloons.
Rick's BarSpred The Dub @ The Green Parrot
Spred The Dub returns to The Green Parrot in Key West for a three day run of live jams. The run includes three sets on each of the first two days and a single closing set on the last day.
SESSION 1 of Big Pine Summer Reading: Dinosaur Hatching
Session 1 of Big Pine Summer Reading features Dinosaur Hatching at Big Pine Library, led by Beakers and Bugs. Participants explore what it means for an animal to be oviparous and how dinosaurs hatch, then learn about the stages of a dinosaur’s life cycle. Everyone will create and paint a dinosaur egg, inspired by a cute plush baby dinosaur to take home. Space and materials are limited, and participants are asked to sign up for only one session, either session 1 or session 2.
Big Pine Key LibrarySESSION 2 of Big Pine Summer Reading: Dinosaur Hatching
Session 2 of Big Pine Summer Reading features Dinosaur Hatching at the Big Pine Library, presented by Beakers and Bugs. Explore which animals come from eggs and what oviparous means, and learn that dinosaurs hatch from eggs. Create and paint a dinosaur egg inspired by a plush baby dinosaur that you can take home, with a look at the dinosaur life cycle included. Spots and supplies are limited, and participants should sign up for either session 1 or session 2.
Big Pine Key LibraryA Pirate Looks Back: Jimmy Buffett Tribute Show
A lunchtime tribute takes the stage in the heart of Key West, presented live for a midday audience. With so many places to eat lunch nearby, it adds a touch of live performance to the middle of the day. Reservations are recommended.
Comedy Key WestJonathan Williams at Schooner Wharf Bar & Grill on Friday, Jul 24, 2026
Originally from Philadelphia and now based in Key West, Jonathan Williams brings nearly 15 years of experience to the stage at Schooner Wharf Bar. His performance features a wide-ranging set of hits that spans five decades, highlighting his range and seasoned musicianship.
Schooner Wharf BarHemingway Adventure
Set out from Higgs Beach in Key West for a bike ride to Baby's Coffee and back, covering about 30 miles round trip. Spend some time around town afterward, then take part in the Hemingway 5K near Southernmost Beach Cafe. Bring your own bike or rent one, and register for the 5K individually.
Higgs BeachSummer Reading: Rocking Through Space
Participants can build a model asteroid, handle a meteorite estimated to be about 4,700 years old, watch a comet created in a live demonstration, and learn a surprising detail about lunar rocks. The focus is on hands-on space science activities.
Big Pine Key Library🌿 Celebrate World Mangrove Day with Coastlove & the Key West Aquarium! 🌎
At Island Farms on Stock Island, a World Mangrove Day community cleanup and mangrove propagule collection invites volunteers to remove marine debris and gather viable baby mangroves for restoration work. This shoreline is one of the few remaining undeveloped stretches in the Lower Keys, where tides naturally deposit both floating litter and propagules, making it a valuable place for hands-on conservation and learning. A large share of the propagules used in Coastlove’s restoration projects last year came from this effort, helping power future outplanting throughout the Keys. Participation directly supports healthier coastlines, improved water quality, expanded wildlife habitat, and stronger island resilience while highlighting the essential role mangroves play in protecting the Florida Keys. Attendees are encouraged to bring sun protection, insect repellent, shoes suitable for getting wet and muddy, and a reusable water bottle. This effort is made possible with support from the Key West Aquarium.
Island Farm on Cow Key, Stock Island, FLTommy Patrick at Tiki House Key West!!
Tommy Patrick brings an acoustic set to Tiki House Key West, with a possible guest spot from his brother Oscar on percussion. Expect lively energy and a relaxed vibe throughout the performance.
BINGO @ The Green Parrot Bar
A bingo night at The Green Parrot Bar brings together the community’s creative and artistic spirit to raise funds for local nonprofits. This event supports Reef Relief’s programs. Cards cost $1, prizes are awarded after each round, and 100 percent of the money raised goes to Reef Relief.
Just George at Rick's Bar Key West on Monday, Jul 27, 2026
Just George brings live music to Rick's Bar in Key West.
Rick's BarSummer Reading: Painting Workshop
Explore painting in a free, hands-on workshop where you can learn as you go and finish a personal work of art. Everyone is welcome, from first-time painters to those looking for a creative break with brushes and color.
Big Pine Key LibraryComedy Key West Open Mic at Comedy Key West on Tuesday, Jul 28, 2026
Comedy Key West presents an open mic that bills itself as the only one in Key West spanning comedy, music, variety, and a hint of impropriety. Performers of all kinds are welcome, including comedians, musicians, poets, and anyone still figuring out where they fit. Participants take the stage at Comedy Key West, with signups part of the process for those seeking a turn at the mic.
Comedy Key WestDolphin Sunset Celebration at Dolphin Research Center
Dolphin Research Center presents a new after-hours experience offered once each month. After the gates close, stay for an intimate evening that centers on connection with the dolphins and the experts who care for them. Take part in the animals’ evening enrichment by hand-feeding a favorite treat, dolphin-safe jello, for a close-up interaction. Continue the night with relaxed conversations as marine mammal professionals answer questions about dolphin intelligence, training, behavior, and conservation. As the sky shifts from golden hour to twilight, enjoy a champagne toast while the colors of sunset spread across the water and the sounds of the dolphins and nearby waves set the scene in the Florida Keys. Availability is limited due to the small-scale format. Members should check email for the monthly booking code to access member pricing.
Dolphin Research CenterSummer Bingo Night (Free Entry)
Enjoy a lively summer bingo night at Key West Theater with music from DJ Sanaris. Play for prizes and gift certificates while relaxing in cool air conditioning. Admission is free, bingo cards are $5, and a two drink minimum applies. This event is for ages 21 and over. Bring friends and a lucky charm for extra fun.
Key West Theater2026 Mini Lobster Season - Stay at Sun Outdoors Marathon
Two action packed days on the water mark the start of the Florida Mini Lobster Season around Sun Outdoors Marathon. Clear coastal waters become a destination for lobster seekers from across the Keys, welcoming experienced divers with tickle sticks as well as first timers eager to try their hand. Set in the heart of the action, Sun Outdoors Marathon serves as a convenient base with quick access to many favored Middle Keys lobster locations. After time on the boat, the marina provides a spot to clean the day’s catch and unwind by the water. A friendly community vibe rounds out the experience, with plenty of chances to trade stories and share tips with fellow hunters at the resort.
Summer Reading: End of Summer Party at the Big Pine Library
Celebrate the close of summer and the completion of Summer Reading at Big Pine Library. This finale features games, creative arts and crafts, and additional prizes, all centered on recognizing the reading you accomplished. The celebration is open to everyone.
Big Pine Key LibraryName the Bar/Blessing of the Fleet
An annual tradition at Keys Fisheries invites the community to choose the name of the upstairs tiki bar for the year ahead. The “Shannon’s” portion remains in honor of Keys Fish family member Shannon Gosselin. The current name is Shannon’s Shuck Shack, and fresh ideas are welcome for the next chapter. Entries cost $1, every dollar supports local charities, and the winning submission earns naming rights for one year along with a $100 gift card, a t-shirt, and bragging rights for the year. Suggestions can be funny, bold, tiki themed, or seafood inspired. Submit entries upstairs, enjoy a cocktail, and help shape what everyone will be calling the bar next year. The chosen name will be revealed during the annual Blessing of the Fleet Party, a celebration with DJs, a buffet, fireworks, cold drinks, and the lobster fleet heading out to kick off another season in the Keys.
Marathon's America-Fest - Celebrating 250 Years of Independence
Marathon Community Park sets the stage for a patriotic celebration of 250 years since the signing of the Declaration of Independence. The event blends history, adventure, and classic summer fun across the grounds and at the amphitheater. Festivities begin with games and music, followed by an interactive treasure hunt that invites all ages to explore the park in search of clues and history themed surprises. After the hunt, the amphitheater hosts an outdoor screening of National Treasure for a fitting finale to a day of discovery. Complimentary hot dogs, chips, and drinks are available, and kids can enjoy a bounce house and dedicated games area. A live DJ keeps the crowd dancing with upbeat music. One or more City Council members may be in attendance.
Marathon Community ParkCommunity Back to School Festival/Festival Comunitario de Regreso a Clases
The second annual community back to school festival at Kirk of the Keys features crafts, activities, animals, a bounce house and water slide, raffle prizes, food, drinks, and more. On arrival, guests can go inside to pick up a raffle ticket and a pencil bag with supplies, then head to the back to enjoy the festivities. The festival is free and encourages attendees to gather school supplies as they get ready for the new school year, all in a spirit of community appreciation.
Kirk of the KeysLobsterfest 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 ResortBusiness 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 CommerceAugust'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 ResortBusiness 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 DermatologyRum Fest Key West 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.
Jesse 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 TheaterBuckcherry
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 TheaterDolphin Sunset Celebration at Dolphin Research Center
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 CenterFriends 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.
Through the Lens – Early Buffett Concert Photography Exhibit Meet & Greet
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 & SpaBubba 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.
Margaritaville 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 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.
Through the Lens – Early Buffett Concert Photography Exhibit
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 & SpaKeep 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.
Party In The Park: Tribute to Bubba
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 ParkTales 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 Adventures Key WestNew 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 West