4th Street Bar & Grill brings a brick-lined, game-day-friendly vibe with a full menu of American eats and a fully stocked bar. The…
132 N 4th St #1200 (Lake Mary)
“4th Street Bar & Grill brings a brick-lined, game-day-friendly vibe with a full menu of American eats and a fully stocked bar. The pet-friendly patio lined with palm trees plus weekly trivia, music bingo, and live music make it an easy go-to just over in Lake Mary.”
From the Winter Springs newsletter, September 7, 2026
When you want a spot that handles both taco cravings and roll-wrapped fixes, Selva Rosa Cocina & Bar delivers with fire-touched plates,…
901 S Orlando Ave (Maitland)
“When you want a spot that handles both taco cravings and roll-wrapped fixes, Selva Rosa Cocina & Bar delivers with fire-touched plates, bright chilled bites, and cocktails that actually earn their garnish. Expect arrachera tacos, bao buns, and a Taco Tuesday plus Happy Hour that make lingering the default.”
From the Winter Park newsletter, September 13, 2026
Ten10 Brewing Company keeps it un-fussy with a DIY brew crew vibe, housemade beers, and the kind of bar snacks and sandwiches that…
1010 Virginia Dr
“Ten10 Brewing Company keeps it un-fussy with a DIY brew crew vibe, housemade beers, and the kind of bar snacks and sandwiches that disappear fast. Weekly run club and trivia nights, plus a "third-best in Orlando" nod, make it a laid-back spot that's an easy hop for Apopka locals.”
Permanent Vacation in Maitland is a cozy, immersive cocktail spot serving rum-centric drinks and tropical food in a cheeky nautical…
106 Lake Ave (Maitland)
“Permanent Vacation in Maitland is a cozy, immersive cocktail spot serving rum-centric drinks and tropical food in a cheeky nautical setting, perfect for those post-work evenings when you want island vibes without leaving the neighborhood, just a short hop from Winter Park and dangerously easy to make a habit.”
From the Winter Park newsletter, September 5, 2026
Living Vitalitea Brewery brews raw, unfiltered kombucha the traditional way, cold brewed with 100% real organic ingredients and whole-plant…
6270 Edgewater Dr Unit 4600
“Living Vitalitea Brewery brews raw, unfiltered kombucha the traditional way, cold brewed with 100% real organic ingredients and whole-plant botanicals. Central Florida based and big on community, they source local when possible, brew weekly, and deliver a crisp probiotic kick that actually tastes like a treat.”
Looking for that easy night near home, Ivanhoe Park Brewing Company pours an award-winning lineup like the Best Florida Beer gold medalist…
1300 Alden Rd
“Looking for that easy night near home, Ivanhoe Park Brewing Company pours an award-winning lineup like the Best Florida Beer gold medalist Park Hopp’r Pilsner, plus rotating food trucks and community-friendly events. Sip local, swap stories, and find a new favorite from Joyland IPA to Guavacation Sour.”
Florida's Largest Oyster Bar, family-owned since 1979, Victorio's Oyster Bar & Grille keeps it simple with the best oysters money can buy,…
300 Dog Track Rd (Longwood)
“Florida's Largest Oyster Bar, family-owned since 1979, Victorio's Oyster Bar & Grille keeps it simple with the best oysters money can buy, freshly prepared seafood, and homemade sauces and pizza dough. Longwood folks, consider this your midweek easy choice when craving something coastal and comforting.”
From the Altamonte Springs newsletter, August 28, 2026
Founded in 2015 by longtime friends Bobby Bowen and Kevin Wigen, Bowigens Beer Company channels their east coast music scene creativity…
1014 FL-436 (Casselberry)
“Founded in 2015 by longtime friends Bobby Bowen and Kevin Wigen, Bowigens Beer Company channels their east coast music scene creativity into seriously good craft brews at the nearby Casselberry taproom and Avalon Park outpost. Check the What's On Tap and Events pages when you're plotting your next Winter Park pint.”
From the Winter Park newsletter, September 1, 2026
RusTeak Ocoee is a fun, polished casual New American restaurant and wine bar run by Culinary Institute of America grads since 2012, pairing…
1681 Amazing Way (Ocoee)
“RusTeak Ocoee is a fun, polished casual New American restaurant and wine bar run by Culinary Institute of America grads since 2012, pairing quality meals made with fresh local ingredients with diverse wines, craft cocktails, and hyper local beer... a reliable go-to when weeknights need a little shine.”
Packwoods nails the classy-meets-cozy vibe with a menu that reads like a story, plus an on-site liquor store so your favorite pour can ride…
360 E Horatio Ave #500 (Maitland)
“Packwoods nails the classy-meets-cozy vibe with a menu that reads like a story, plus an on-site liquor store so your favorite pour can ride home with you. Keep an eye on their events calendar for expert-led classes, exclusive tastings, and a legit Whiskey Club.”
From the Winter Garden newsletter, September 15, 2026
When you want a fresh pour without the fuss, Windermere Brewing Company keeps small-batch beer flowing, plus guest taps, cider and a shaded…
111 W 5th Ave (Windermere)
“When you want a fresh pour without the fuss, Windermere Brewing Company keeps small-batch beer flowing, plus guest taps, cider and a shaded porch that insists you linger. Live music, trivia, food trucks, yoga and a run club make it your easy midweek reset and weekend vibe... go claim your spot this week.”
Cork & Olive in nearby Lake Mary pairs freshly made pastas with a Wine Spectator recognized list, plus OpenTable and Nextdoor kudos. They…
1061 S Sun Dr Ste 1009 (Lake Mary)
“Cork & Olive in nearby Lake Mary pairs freshly made pastas with a Wine Spectator recognized list, plus OpenTable and Nextdoor kudos. They have been part of the community for over 16 years and can custom build vegan, vegetarian, or gluten free plates, so your whole crew can linger over dinner and a great pour.”
From the Winter Springs newsletter, September 5, 2026
Brewlando Maitland brings its signature craft beer experience to a laid-back spot with tasty bites, community events, and enough range for…
160 Independence Ln Ste B (Maitland)
“Brewlando Maitland brings its signature craft beer experience to a laid-back spot with tasty bites, community events, and enough range for a quiet pint or a lively meetup. This week, if your schedule needs a no-fuss reset, their brews and weekend brunch lineup will absolutely do the trick.”
From the Altamonte Springs newsletter, August 24, 2026
Alestone Brewing Co. pours handcrafted ales and lagers in Historic Downtown Longwood, with a lineup that swings from crisp Czech pils to…
351 N Ronald Reagan Blvd #1055 (Longwood)
“Alestone Brewing Co. pours handcrafted ales and lagers in Historic Downtown Longwood, with a lineup that swings from crisp Czech pils to fruited sours and the decadent Daath imperial stout series, plus artisan pizza and toasted sandwiches that make sticking around for a flight feel mandatory.”
From the Winter Garden newsletter, September 1, 2026
Toll Road Brewing Company, Ocoee’s first and finest craft brewery, is pouring award-winning house beers alongside a rotating mix of guest…
101 W McKey St (Ocoee)
“Toll Road Brewing Company, Ocoee’s first and finest craft brewery, is pouring award-winning house beers alongside a rotating mix of guest taps in an inviting taproom. Peek their events calendar for trivia, live music, and food trucks, then snag your favorites to-go for an easy weeknight win.”
Bounce House Social Eats is serving refined cocktails and seriously fun comfort food, from Drunken Taters and Larry Curds to jumbo wings in…
12100 Challenger Pkwy
“Bounce House Social Eats is serving refined cocktails and seriously fun comfort food, from Drunken Taters and Larry Curds to jumbo wings in Buffalo, Lemon Pepper, or Korean Buffalo. Grab a friend for weekend brunch or a low-key night out, then eat, drink and bounce.”
Sun On the Beach keeps Four Corners buzzing with karaoke, live music, Latin Sundays, surprise pro wrestling and legit comedy nights, plus…
5770 W Irlo Bronson Memorial Hwy (Kissimmee)
“Sun On the Beach keeps Four Corners buzzing with karaoke, live music, Latin Sundays, surprise pro wrestling and legit comedy nights, plus patio parties at Gilligan's Tiki. Handcrafted cocktails and craveable bites fuel the fun, so snag your crew and make some gloriously questionable memories.”
From the Four Corners newsletter, September 9, 2026
Orlando Comedy Club packs a true comedy room inside Calypso Bar & Grill near I-Drive with stand-up shows, local showcases, weekly open…
6300 Parc Corniche Dr
“Orlando Comedy Club packs a true comedy room inside Calypso Bar & Grill near I-Drive with stand-up shows, local showcases, weekly open mics, cocktails, and easy dinner-then-laughs momentum. Shake off the week, bring a buddy, and let the punchlines do the heavy lifting.”
When you need easygoing bites, a legit beer menu, and live music that gets a little jiggy, Vanbarry's Public House nails the casual vibe.…
4120 S Orange Ave
“When you need easygoing bites, a legit beer menu, and live music that gets a little jiggy, Vanbarry's Public House nails the casual vibe. Great for gametime or familytime, it’s the kind of spot you slide into with friends and somehow stay longer than planned.”
Slip into Ale & Compass Lounge for a cozy, nautical nook serving lively libations and savory snacks. Think beers, wines, top-shelf pours,…
1700 Epcot Resorts Blvd (Lake Buena Vista)
“Slip into Ale & Compass Lounge for a cozy, nautical nook serving lively libations and savory snacks. Think beers, wines, top-shelf pours, plus playful cocktails like the Spicy Pomegranate Margarita or the Captain’s Mai Tai when you need a low-key escape close to home.”
Craving a midweek vibe check, Alafaya? Formaggio & Friends pairs a deep bench of global wines with Florida craft brews and ridiculously…
4745 S Orange Ave
“Craving a midweek vibe check, Alafaya? Formaggio & Friends pairs a deep bench of global wines with Florida craft brews and ridiculously good cheese and charcuterie boards. Drop in this week for a Take Flight tasting or let their sommeliers steer you toward your new favorite bottle.”
Brewlando Brewing keeps Central Florida’s pint game strong with award-winning staples and fun seasonals, so your weekend is basically…
6820 Hoffner Ave
“Brewlando Brewing keeps Central Florida’s pint game strong with award-winning staples and fun seasonals, so your weekend is basically planned. Sip a smooth Altstadt Märzen, dive into the juicy Hop Patriot hazy DIPA, or keep it light with Coupe d’Or, their Belgian-style table beer.”
480 N Wine Bar keeps things lively with a thoughtfully curated lineup of champagne, wine and cocktails, then layers in music and movement…
480 N Orlando Ave Ste 133 (Winter Park)
“480 N Wine Bar keeps things lively with a thoughtfully curated lineup of champagne, wine and cocktails, then layers in music and movement for a night that’s anything but ordinary. Slide in for bubbles, stay for the electric vibe and that deceptively-long-chat-with-a-friend energy.”
Where classic meets iconic, Still Lounge by Dre and Snoop brings a polished cocktail scene with hip-hop swagger, spinning live DJs and…
9101 International Dr #2210
“Where classic meets iconic, Still Lounge by Dre and Snoop brings a polished cocktail scene with hip-hop swagger, spinning live DJs and throwback playlists. Sip a Platinum Negroni, OG-OF, or G-Thang, then settle into the high-style vibe that makes even a random Thursday feel like an event.”
From the Winter Garden newsletter, September 8, 2026
Mulligan's Irish Pub brings easygoing Irish pub vibes, solid pub grub and properly poured pints for after-work decompression. Grab your…
39 Blake Blvd (Kissimmee)
“Mulligan's Irish Pub brings easygoing Irish pub vibes, solid pub grub and properly poured pints for after-work decompression. Grab your crew for trivia, karaoke or jukebox bingo and pretend it’s just “one drink” while you accidentally make midweek plans you’ll actually keep. Check it out.”
Need an easy win this week? Tooting Otter keeps it simple with local craft brews and curated wine on tap, riverside views that do the heavy…
1014 Miami Springs Dr (Longwood)
“Need an easy win this week? Tooting Otter keeps it simple with local craft brews and curated wine on tap, riverside views that do the heavy lifting, and live music on weekends. Swing by Wekiva Island, grab a seat, and let the vibes outwork your to-do list.”
When it’s sticky out and you want something cold and fun, Fat Tuesday at Old Town serves frozen cocktails like the legendary 190 Octane,…
5770 W Irlo Bronson Memorial Hwy Suite 115 (Kissimmee)
“When it’s sticky out and you want something cold and fun, Fat Tuesday at Old Town serves frozen cocktails like the legendary 190 Octane, Cat 5 Hurricane, and Miami Vice, plus those souvenir cups you’ll totally justify keeping... perfect for a midweek chill or weekend wander.”
Casa Vieja - Orlando Florida hits the spot when abuela-level flavors are calling and your kitchen is on strike. Traditional Puerto Rican…
7101 S Orange Ave
“Casa Vieja - Orlando Florida hits the spot when abuela-level flavors are calling and your kitchen is on strike. Traditional Puerto Rican specialties in a vibrant, easygoing setting, plus handy Catering To Go if you need to feed a crowd... consider this your midweek Kissimmee cheat code.”
Quicksand Wine Bar keeps it neighborhood-friendly with a cozy bar vibe, pouring natural wines that lean interesting without getting…
1903 E Colonial Dr
“Quicksand Wine Bar keeps it neighborhood-friendly with a cozy bar vibe, pouring natural wines that lean interesting without getting precious. It’s the kind of spot for an easy catch-up or date night, and yes, they’ve got gift cards when you need a clutch last-minute present.”
From the Winter Park newsletter, September 7, 2026
Orlando’s first meadery, Zymarium Meadery, pours 20+ meads from dry to dessert, traditional to modern, all gluten-free and made with local…
1121 N Mills Ave
“Orlando’s first meadery, Zymarium Meadery, pours 20+ meads from dry to dessert, traditional to modern, all gluten-free and made with local unheated honey. An easy day trip treat for New Smyrna, and yes, they were named among the top meaderies in the world.”
Craving a cozy spot for British pub classics, a proper pint, and some live tunes or trivia close to home? The Fox & Hounds Public House…
3514 W Vine St (Kissimmee)
“Craving a cozy spot for British pub classics, a proper pint, and some live tunes or trivia close to home? The Fox & Hounds Public House delivers a true taste of Britain in Kissimmee since 1984, with game-day gatherings, crowd-pleasing specials, and an easygoing vibe locals actually claim as theirs.”
Whether you’re chasing the mic or just the jukebox, Rockin' Rhonda's delivers a low-key neighborhood hang with beer, wine, cocktails and…
2617 S Orlando Dr (Sanford)
“Whether you’re chasing the mic or just the jukebox, Rockin' Rhonda's delivers a low-key neighborhood hang with beer, wine, cocktails and plenty to do. Weekly trivia, darts, pool tournaments and karaoke with Rhonda keep the energy fun and familiar, plus they’ve got TVs for the game and occasional live music.”
Wine O'Clock Bistro makes wine fun, not fussy, with self-serve tasting machines that let you explore rare pours or find your new weeknight…
110 W McKey St (Ocoee)
“Wine O'Clock Bistro makes wine fun, not fussy, with self-serve tasting machines that let you explore rare pours or find your new weeknight go-to. Pair your picks with curated cheeses, charcuterie, and a signature flatbread, then snag a bottle for later... future you will be thrilled.”
Eola Wine Company keeps it relaxed with boutique wines poured 50-deep by the glass, easygoing flights of four, and light bites like…
430 E Central Blvd · ✓ checked Aug 20
“Eola Wine Company keeps it relaxed with boutique wines poured 50-deep by the glass, easygoing flights of four, and light bites like charcuterie and flatbreads. Grab a seat outside, sample around, then commit to a favorite pour your weeknight will thank you.”
If your group chat needs a new go-to, Lamp & Shade Craft Kitchen and Cocktails mixes playful, Asian-leaning small plates with cocktails…
1336 N Mills Ave
“If your group chat needs a new go-to, Lamp & Shade Craft Kitchen and Cocktails mixes playful, Asian-leaning small plates with cocktails worth lingering over. Set in a former lamp store locals remember, it nails the 'let's throw some shade' vibe and turns out lively brunch, too.”
Scratch-made favorites, from fresh fish and prime cuts to what they proudly call Orlando's best burger, pair with 30+ wines, cocktails, and…
549 W Par St
“Scratch-made favorites, from fresh fish and prime cuts to what they proudly call Orlando's best burger, pair with 30+ wines, cocktails, and plenty of taps at The Tap Room at Dubsdread this week. Grab a seat on the verandah with fairway views or cozy up inside and make a regular night feel special.”
Craving a spot that actually blends good plates, strong cocktails, and a scene? Euphoria Kissimmee brings the nightlife energy with live…
2783 N Orange Blossom Trail (Kissimmee)
“Craving a spot that actually blends good plates, strong cocktails, and a scene? Euphoria Kissimmee brings the nightlife energy with live entertainment, party-ready events, chef-driven bites, and a vibe that turns a random Tuesday into a story, so grab your crew and make it your midweek reset.”
From the Celebration newsletter, September 16, 2026
Wine 4 Oysters Bar & Bites turns weeknights into mini vacations with raw flights topped with Prosecco or beer granita, sesame seaweed and…
1957 S Alafaya Trail
“Wine 4 Oysters Bar & Bites turns weeknights into mini vacations with raw flights topped with Prosecco or beer granita, sesame seaweed and caviar, plus baked beauties like Rockefeller and Kilpatrick. Pair it with a glass of something crisp, then keep snacking on house-smoked tuna dip or a seafood boil.”
Crooked Can Brewing Company keeps the taps lively with core classics, seasonals, and small-batch creativity, all brewed with serious…
426 W Plant St (Winter Garden)
“Crooked Can Brewing Company keeps the taps lively with core classics, seasonals, and small-batch creativity, all brewed with serious passion. Grab a fresh pour, wander Plant Street Market for artisan bites, and if you’re feeling curious, hop a brewery tour this week.”
From the Winter Garden newsletter, September 19, 2026
The Crazy Cork Wine Bar brings Italy to Oviedo with a 21+ calm vibe, handpicked boutique wines, and seasonal, scratch-made plates including…
on the lake, across from dog park, 940 City Plaza Way (Oviedo)
“The Crazy Cork Wine Bar brings Italy to Oviedo with a 21+ calm vibe, handpicked boutique wines, and seasonal, scratch-made plates including signature focaccia baked with imported Italian flour. Winner of a 2026 Orlando Sentinel Foodie Award, it’s the weeknight reset your palate and patience have been begging for.”
With 64 Enomatic self-pour wine taps, 18 PourMyBeer drafts, sommelier recommendations, and shareable small plates, Curious Cork Wine &…
14383 Narcoossee Rd
“With 64 Enomatic self-pour wine taps, 18 PourMyBeer drafts, sommelier recommendations, and shareable small plates, Curious Cork Wine & Provisions makes weeknights feel special. Go swirl, sip by the ounce, learn a thing or two, and reconnect with your crew this week without waiting in line.”
Mathers Social Gathering is where Orlando gathers for vintage libations, live entertainment, and timeless hospitality in a setting inspired…
3 Phoenix Building, 30 S Magnolia Ave
“Mathers Social Gathering is where Orlando gathers for vintage libations, live entertainment, and timeless hospitality in a setting inspired by a bygone era inside the historic Phoenix Building. Treat yourself to a night that feels special, then text the group chat like a hero.”
With seasonal dishes built on bold, modern flavors and a menu of handcrafted drinks that actually pair well with dinner, The Imperial On…
136 S Park Ave (Winter Park)
“With seasonal dishes built on bold, modern flavors and a menu of handcrafted drinks that actually pair well with dinner, The Imperial On Park makes an easy go-to for Winter Park nights. Book a table or wander in, and keep them in mind when you need catering or a polished private gathering.”
Whether your fantasy lineup is winning or you just need an excuse to eat wings, Froggers Grill and Bar brings Apopka the classic combo of…
1601 Rock Springs Rd (Apopka) · ✓ checked Aug 19
“Whether your fantasy lineup is winning or you just need an excuse to eat wings, Froggers Grill and Bar brings Apopka the classic combo of saucy wings, big burgers, pizza, and sports on wall-to-wall TVs, plus pool tables and dartboards. Rally the crew this week, this is your game-night home base.”
Bar Hops pours a rotating lineup of craft beers, seltzers, and easygoing beverages inside Launch Orlando, so you can unwind while the…
610 N Alafaya Trail
“Bar Hops pours a rotating lineup of craft beers, seltzers, and easygoing beverages inside Launch Orlando, so you can unwind while the action plays out around you. Sip like a champ while laser tag, bowling, and trampoline heroics provide the built-in floor show this week.”
For a low-key night and bottles you won’t see at Publix, Digress Wine is College Park’s relaxed wine bar and shop with off-the-beaten-path…
1215 Edgewater Dr
“For a low-key night and bottles you won’t see at Publix, Digress Wine is College Park’s relaxed wine bar and shop with off-the-beaten-path gems worth the short hop from Winter Garden. Ask about the Digress Cellar, where the temperature stays cool and the selections run delightfully deep.”
From the Winter Garden newsletter, September 10, 2026
Whether you’re wrapping up the workday or eyeing a low-key date spot, Imperial Wine Bar nails the relaxed neighborhood vibe with boutique…
1800 N Orange Ave
“Whether you’re wrapping up the workday or eyeing a low-key date spot, Imperial Wine Bar nails the relaxed neighborhood vibe with boutique wines, microbrews, and legit classic cocktails, all tucked inside a stylish furniture store that makes every sip feel like you discovered a secret.”
From the Winter Park newsletter, September 6, 2026
The Egret Bar @ Hall's On 5th is pouring clever signatures and well-made classics, from the hometown-worthy Apopka Spritz to a silky…
15 E 5th St (Apopka)
“The Egret Bar @ Hall's On 5th is pouring clever signatures and well-made classics, from the hometown-worthy Apopka Spritz to a silky Espresso Martini and a confident Hall's Old Fashioned. Slide in, ask the bartenders for a favorite, then act like you discovered it first.”
The Ravenous Pig is brewing its own beer right in Winter Park, pouring everything from crisp golden ales to juicy IPAs and tangy sours,…
511 W Fairbanks Ave (Winter Park) · ✓ checked Aug 21
“The Ravenous Pig is brewing its own beer right in Winter Park, pouring everything from crisp golden ales to juicy IPAs and tangy sours, while the seasonal menu keeps the food game sharp. Grab a spot in the beer garden and make it your midweek treat.”
Grape and the Grain Wine Bar is Orlando’s laid-back spot where global wines meet Florida craft beer, funky art and a backyard scene made…
1110 Virginia Dr
“Grape and the Grain Wine Bar is Orlando’s laid-back spot where global wines meet Florida craft beer, funky art and a backyard scene made for catching live tunes or trivia with friends. They even lean into low or no-alc options, so your weeknights can still feel festive.”
Fiddler's Green Irish Pub & Eatery has been serving the community since 1996 with fresh-from-the-kitchen pub fare, proper pours, and…
544 W Fairbanks Ave (Winter Park)
“Fiddler's Green Irish Pub & Eatery has been serving the community since 1996 with fresh-from-the-kitchen pub fare, proper pours, and regular live entertainment that turns a casual drop-in into a session. It’s the most highly-awarded Irish pub in Central Florida, so rally the crew for ceol, craic agus comhrá.”
Need a reset after a long week in Deltona? Bonkerz Comedy Club - Orlando brings in comedians you’ve seen on TV and in the movies, with…
4270 Aloma Ave (Winter Park)
“Need a reset after a long week in Deltona? Bonkerz Comedy Club - Orlando brings in comedians you’ve seen on TV and in the movies, with handpicked lineups on select Friday and Saturday nights inside The Corner, so you can grab a couple friends, laugh hard, and feel lighter by Monday.”
Over 60 curated wines plus Brewlando’s signature beers on tap make The Winery & Tasting Room by Brewlando an easy yes when you want…
8395 International Dr
“Over 60 curated wines plus Brewlando’s signature beers on tap make The Winery & Tasting Room by Brewlando an easy yes when you want options. Post up at ICON Park, build a flight, and pair it with flatbreads or pizza while the Orlando Eye steals the show.”
Craving a Whose Line-style free-for-all, but with zero filters? Mama's Comedy Show is right nearby with razor-sharp improvisers who riff on…
1010 Virginia Dr
“Craving a Whose Line-style free-for-all, but with zero filters? Mama's Comedy Show is right nearby with razor-sharp improvisers who riff on your wild suggestions, get gleefully inappropriate, and somehow turn chaos into tears-of-laughter moments locals keep quoting all week.”
If you crave inventive, beautifully balanced drinks in a cool speakeasy setting, The Courtesy delivers with Orlando’s first dedicated…
1288 N Orange Ave (Winter Park)
“If you crave inventive, beautifully balanced drinks in a cool speakeasy setting, The Courtesy delivers with Orlando’s first dedicated cocktail bar pedigree and a warm, swanky vibe. They even run a hands-on class where you build three cocktails from scratch... perfect for leveling up your home bar game.”
From the Winter Garden newsletter, September 12, 2026
Craving no-fuss comfort food and a good pint? Ollie’s Public House is a casual neighborhood spot with live music energy, a big menu that…
3400 Edgewater Dr
“Craving no-fuss comfort food and a good pint? Ollie’s Public House is a casual neighborhood spot with live music energy, a big menu that runs from stacked sandwiches to pizza, and a dedicated beer menu to back it up. Rally the crew and make a night of it this week.”
If your week needs a little speakeasy kick, Morse Code Lounge delivers plush vibes, a curated wine list, shareable bites, and DJ nights…
163 E Morse Blvd (Winter Park)
“If your week needs a little speakeasy kick, Morse Code Lounge delivers plush vibes, a curated wine list, shareable bites, and DJ nights that actually feel grown up. Reserve a table, gather a few friends, and turn an ordinary evening into something you’ll talk about all week.”
Leather-seat lounging, crafty cocktails, and a legit bourbon lineup make Oviedo Park Pub an easy after-work default. It lives inside The…
888 City Walk Ln #1024 (Oviedo)
“Leather-seat lounging, crafty cocktails, and a legit bourbon lineup make Oviedo Park Pub an easy after-work default. It lives inside The Food Factory, so you can pair your pint with sushi, pizza, or whatever you’re craving, plus trivia, music, and big-game energy keep the nights lively.”
Whether you're pre-show, post-errands, or just craving a low-key hang, 98Forty Tapas & Tequila serves shareable Mexican bites with legit…
9840 International Dr
“Whether you're pre-show, post-errands, or just craving a low-key hang, 98Forty Tapas & Tequila serves shareable Mexican bites with legit freshness, think ceviches, salsas, and fresh-cut guac plus a lineup of forty premium tequilas. Inside Rosen Centre, it’s a solid spot for small plates that actually satisfy.”
The Wine Room on Park Avenue lets you explore 100+ wines from their machine dispensers, then graze on artisanal cheeses and tapas. A comfy…
270 S Park Ave (Winter Park) · ✓ checked Sep 10
“The Wine Room on Park Avenue lets you explore 100+ wines from their machine dispensers, then graze on artisanal cheeses and tapas. A comfy rustic-casual spot for Winter Park folks who like to try a little of everything, chat, and find a new favorite.”
From the Winter Park newsletter, September 16, 2026
Whether you're wine-curious or just need a midweek reset, Open Container Wine Bar pours adventurous Armenian varietals in an out-of-the-box…
8200 Vineland Ave Unit 281
“Whether you're wine-curious or just need a midweek reset, Open Container Wine Bar pours adventurous Armenian varietals in an out-of-the-box tasting led by professionally trained sommeliers, with options by the glass or bottle after. Book a private tasting or jump into their interactive events.”
SAK Comedy Lab has been turning audience suggestions into characters, scenes and songs since 1991, with shows like Duel of Fools and King…
55 W Church St #211
“SAK Comedy Lab has been turning audience suggestions into characters, scenes and songs since 1991, with shows like Duel of Fools and King of the Hill. Think Whose Line vibes, and yep, Wayne Brady got his start here, plus classes if you’ve been secretly rehearsing in the shower.”
Black Hammock Lazy Gator Bar Venue is your excuse to catch a Lake Jesup sunset with an ice-cold brew or cocktail, then crush some crispy…
2356 Black Hammock Fish Camp Rd (Oviedo)
“Black Hammock Lazy Gator Bar Venue is your excuse to catch a Lake Jesup sunset with an ice-cold brew or cocktail, then crush some crispy fried gator tail and catfish while airboats buzz the shoreline. It’s laid-back, a little wild, and exactly the midweek reset you’ve been needing.”
Set in a former Florida hardware landmark, 1881 Restaurant & Bar pairs a globally inspired menu with Kissimmee soul. Swing by this week for…
308 Broadway (Kissimmee)
“Set in a former Florida hardware landmark, 1881 Restaurant & Bar pairs a globally inspired menu with Kissimmee soul. Swing by this week for steaks, fresh seafood, and unexpected Eastern Uzbek dishes, then linger over thoughtful wine selections and handcrafted cocktails.”
Quantum Leap Winery, Florida's only sustainable winery, partners with sustainable and organic growers worldwide to pour quality wines with…
3201 Corrine Dr #106a
“Quantum Leap Winery, Florida's only sustainable winery, partners with sustainable and organic growers worldwide to pour quality wines with a lighter footprint.”
From the Titusville newsletter, September 13, 2026
Cozy and Tuscan-styled, Vintage Vino pours well-chosen wines, offers tasty cheeses, and keeps a few craft beers on deck, plus a retail wall…
310 Broadway (Kissimmee)
“Cozy and Tuscan-styled, Vintage Vino pours well-chosen wines, offers tasty cheeses, and keeps a few craft beers on deck, plus a retail wall so you can leave with the bottle you just fell for. That’s an easy midweek plan when you’re dodging grocery-aisle roulette.”
Hanson's Shoe Repair hides behind a daily password and rewards the curious with intimate speakeasy vibes, a rooftop perch, and cocktails…
27 E Pine St
“Hanson's Shoe Repair hides behind a daily password and rewards the curious with intimate speakeasy vibes, a rooftop perch, and cocktails that skew classic but never boring. Track the password on Twitter, then treat yourself to a proper nightcap this week.”
Skip the crowded bars and slip into The Vintage Speakeasy Bistro in Hunter's Creek, where a door password leads to handcrafted,…
13526 Village Park Dr Unit 208
“Skip the crowded bars and slip into The Vintage Speakeasy Bistro in Hunter's Creek, where a door password leads to handcrafted, prohibition-era cocktails, a house jazz band, and relaxed white-glove vibes. Perfect for Poinciana locals craving a low-key, grown-up evening that still feels special.”
Craving an easy hang that still feels a little special? Urban On Plant Kitchen & Bar brings brick-oven flatbreads, comforting American…
132 W Plant St (Winter Garden)
“Craving an easy hang that still feels a little special? Urban On Plant Kitchen & Bar brings brick-oven flatbreads, comforting American favorites, and craft cocktails to downtown Winter Garden, a lively spot to connect and unwind this week... think Buffalo Chicken flatbread, an Urban Burger, and a friend-worthy round.”
From the Winter Garden newsletter, September 18, 2026
Johnny's Fillin' Station has been the kind of family-run bar and grill that makes weeknights feel like a win since 1985. This week, think…
2631 S Ferncreek Ave
“Johnny's Fillin' Station has been the kind of family-run bar and grill that makes weeknights feel like a win since 1985. This week, think famous Patty Melt, jumbo wings, and dangerously snackable Mac & Cheese Bites, plus other comforting standbys that taste like home and pair perfectly with catching up.”
