Please confirm details with event organizers or venues in case of changes or cancellations.
ONGOING
Daily
Mini Golf
Ramrod Key: This kid-friendly 18-hole course boasts a fun caveman theme with two giant waterfalls and four fountains. And get this: If you’re 21+, you and your friends can have a cocktail or glass of wine while you putter around. Happens daily from 10 am – 10 pm at Boondocks Grille & Draft House at 27205 Overseas Hwy (MM 27.5). Info: 305-872-4094; boondocksfloridakeys.com.
Miniature Golf
Marathon: The Keys’ newest and largest mini-golf attraction is a full-size, 18-hole course that challenges the best of the best. Lush landscaping and an impressive local coral rock waterfall makes it one of the Middle Keys’ “Must See” destinations. Top it all off with a variety of snacks, slushies, frozen daiquiris, or cold beer. Open daily from 10 am – 10 pm at Porky’s Bayside, 1410 Overseas Hwy. Info: 305-731-7592; porkysbaysidebbq.com.
Snook’s Bayside Sunset Celebration
Key Largo: Kick back with a rum punch on Snook’s 5,000-square-foot waterfront patio, listen to some great live music, and enjoy an unobstructed panoramic view of the sun sinking into Florida Bay. The nightly event is ceremoniously marked by the “Sunset Horn” bellowing just before the fiery ball disappears into the horizon. The fun continues well after dark with live entertainment and dancing under the palms. Daily Happy Hour from 4 – 6 pm. Takes place at Snooks Bayside & Grand Tiki at MM 99.8, Southbound Lane, behind the Sandal Factory outlet. Info: 305-453-5004; snooks.com.
Bayside Sunset Celebration
Key Largo: Located on the first floor of the Bayside Grille, the Bayside Sunset Bar is regaled for having the “Most Photographed Sunset in Key Largo.” The daily Sunset Celebration here features a lively Happy Hour, tropical libations, a fun menu, top performers, and a grand finale beachside Conch Shell Blowing. FYI: On select nights, you can also catch some powerful beats from internationally renowned blues bands. Takes place at Bayside Sunset Bar, 99540 Overseas Hwy (MM 99.5 Bayside, Behind DiGiorgio’s Cafe Largo). Info: 305-451-3380; baysidegrill.com.
Lor-e-Lei Sunset Celebration
Islamorada: As that big ball of fire starts to sink into the horizon, the live music kicks in, and the bar crowd spills onto the beach for some serious toes-in-the-sand revelry. On most nights, just after sunset, magician Michael Trixx, who was featured on “America’s Got Talent,” performs a “Rock-N-Roll Magic Show” that will blow your mind. Daily Happy Hour from 4 – 6 pm with Well Drinks for just $4, Domestic Drafts at only $3, and the island’s best Margarita menu. It all happens at Lorelei Restaurant & Cabana Bar, 96 Madeira Rd. FYI: Look for the giant mermaid at MM 82, Bayside. Info: 305-664-2692; loreleicabanabar.com.
Key West Sunset Celebration
Key West: Each evening, about two hours before sunset, flocks of people gather at Key West’s Mallory Square and on the docks behind the Opal Resort & Marina to watch the sun slowly sink into the Gulf of Mexico and revel in the colorful street performers, local artists, psychics, and food vendors who have made Key West’s spectacular Sunset Celebration a world-famous, multicultural happening. Info: sunsetcelebration.org.
Nightly
Aquaplex
Key West: With three reinvented venues all under one roof, Key West’s state-of-the-art entertainment complex also boasts a lovely outdoor garden bar, lively dance bar and the best drag shows in the Keys. But the crowning jewel of it all is the Birdcage Cabaret, which features the world-renowned female impressionist and singer, Christopher Peterson, and The Aquanettes, an outrageous troupe of talented drag queens. Find it all at the Aquaplex, 711 Duval St. Info: 305-294-0555; aquakeywest.com.
WEEKLY
Monday – Tuesday
Glow Hours: Rooftop Happy Hour on Hugh’s View
Key West: For a headier Happy Hour, head up to Hugh’s View, where the bar is open, admission is free, and everyone looks great in golden twilight. The rooftop happening offers panoramic vistas across Old Town — from the Gulf of Mexico on one side to the Atlantic on the other. Takes place from 5 pm through sunset at The Studios of Key West, 533 Eaton St. Info: 305-296-0458; tskw.org.
Every Thursday
Key West Waterfront Farmers Market
Key West: This traditional farmers’ market includes a huge variety of seasonal produce and other goodies. You can also shop for local arts & crafts, flea market finds, jewelry, clothing, cigars, and CBD products. Takes place from 2 – 7 pm at Truman Waterfront Park (end of Southard St). FYI: Make sure to bring your own bags. Info: 305-731-3385; keysartisanmarket.com
Select Sundays
Key West Artisan Market
Key West: This juried market celebrates the best of the Keys’ creative community with a curated selection of fine crafts, art, jewelry and more. Rotating themes feature local non-profits, live remotes, musicians, and local authors, as well as food and drink options. Takes place from 10 am – 2 pm on select Sundays at the Sony McCoy Indigenous Park, 1801 White St. Info: 305-731-3385; keysartisanmarket.com.
MONTHLY
Last Wednesday
Dolphin Sunset Celebration
Marathon: What’s better than a margarita at sunset? How about sharing a non-alcoholic Jello shot with a dolphin! This totally unique Sunset experience is your opportunity to interact with dolphins, chat with experts, and discover what it means to build meaningful relationships with these special animals. As the sky turns gold, you can enjoy a champagne toast to the setting sun, surrounded by playful dolphins, an ocean breeze, and unforgettable island beauty. Space is limited, so reserve early! The fun begins at 6:45 pm (May – July) at the Dolphin Research Center, 58901 Overseas Hwy (MM 59 Gulfside) on Grassy Key. Info: 305-289-1121; dolphins.org.
Third Saturday
Native Plant Sale
Key West: Peruse over 2,000 native, rare, and endangered plants from the Keys, Cuba, and the Western Caribbean at this terrific monthly plant sale. Takes place from 9 am – Noon at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.
First Fridays
First Fridays on Fleming
Key West: This monthly “shop local” evening stroll along historic Fleming St showcases vibrant boutiques, galleries, antique stores, artist studios, eateries and other creative businesses. Lots of cool special events, too! Takes place from 6 – 9 pm along the 500 Block of Fleming St, all the way to Grinnell St. Info: 305-304-9001; fabflemingkw.com.
SPECIAL EVENTS
May 24
Schooner Wharf Bar Minimal Regatta
Key West: Known as “the only boat race you can view from start to finish from shore,” this wacky regatta is also a race to stay afloat. Savvy sailors use minimal materials, including plywood and duct tape, to build their tiny vessels. Races begin at 1:30 pm at Schooner Wharf Bar, 202 William St in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.
May 30
19th Annual Key West Follies
Key West: A precursor to Key West’s annual Pride Celebration, this campy variety show includes an array of unforgettable comedy, singing, dancing, and lots of belly busters. Hosted by Domini Paolillo and Claire Caplan, it’s an outrageous show that gets better and better every year!. Full bar service. Showtime: 6:30 pm. FYI: Always a “sell out,” so get your tickets early! Takes place at the Key West Theater, 512 Eaton St. Info & tickets: 305-985-0433; thekeywesttheater.com.
June 3 – 7
Key West Pride 2026: Color the Island — A Celebration of Identity Through Color and Creativity”
Key West: This year’s dynamic Pride Celebration showcases self-expression, artistry, and authenticity in a full-on tribute to Key West’s legendary “One Human Family” philosophy. The immersive five-day festival boasts an exciting roster of signature events including lively dance parties, sunset sails, daytime pool parties, drag spectaculars, themed bar crawls, live entertainment, and the return of the beloved Pride Street Fair, as well as an electrifying performance by Bertha: Grateful Drag that blends iconic music, high-energy performance, and unapologetic queer artistry. Info and a full event schedule: 305-294-4603; gaykeywestfl.com/pride.
June 5 – 7
33rd Annual Lower Keys Chamber Dolphin Tournament
Little Torch Key: Anglers contend for over $35,000 in cash prizes and awards. Register for the tournament and enjoy appetizers and a cash bar on F, June 5 starting at 5 pm during the special Kick Off Party at Kiki’s Sandbar, 183 Barry Ave. Kiki’s will also host a lively Dinner and Awards Party at 6 pm on Su, June 7. Info: 305-872-2411; lowerkeyschamber.com.
June 8 – 21
Summer Solstice Celebration
Key West: As a unique precursor to this year’s June 20 Solstice — which marks the official first day of summer, a colorful series of special events and performances will take place each evening leading up to the big event. Takes place nightly, starting at 7 pm at Key West’s Mallory Square, 400 Wall St, and on the pier behind the Opal Key Resort & Marina at 245 Front St. Info: sunsetcelebration.org.
June 14 — 21
I Love Stock Island Festival
Key West/Stock Island: This off-beat, annual celebration of music, food and culture also includes a fun, diverse line-up of one-of-a-kind Stock Island-inspired activities. Kick back with great live performances from top artists, indulge in some terrific local culinary creations, and immerse yourself in a wide array of art exhibits and workshops. Various times and locations. It all takes place on Key West’s historic Stock Island. Info: 305-295-9112; ilovestockisland.org.
July 1 – 5
Annual Key Lime Festival
Key West: This long limey holiday weekend includes a full menu of activities, including a Key Lime Sip & Stroll, Key Lime Pie Hop, a gravity-defying Key Lime Pie Drop from the top of the Key West Lighthouse, and the World-Famous Key Lime Pie Eating Championship. It’s one tasty, lip-smacking weekend! Complete event schedule at keylimefestival.com.
July 10 – 11
42nd Annual Underwater Music Festival
Big Pine & The Lower Keys: This world-famous quirky underwater concert for divers, snorkelers, and the occasional mermaid is the summer’s splashiest event! The annual shindig, which promotes reef conservation and preservation, kicks off on F from 6 – 8 pm with live music, lite bites, and beverages at Mote Marine, 24244 Overseas Hwy on Summerland Key. The submerged songfest, which is also broadcast on US Radio104.1 FM, takes place Sa from 10 am – 2 pm at Looe Key Reef in the Florida Keys National Marine Sanctuary, approximately 5 miles south of Big Pine Key. Transportation is available from local diving shops. Info: 305-872-2411; lowerkeyschamber.com.
July 17 – 19
Mel Fisher Days Celebration
Key West: This annual charity event tributes to rum-and-coke drinking, gold-chain-adorned Keys character Mel Fisher. Celebrated as “the world’s greatest treasure hunter,” Fisher’s 1985 discovery of the Nuestra Señora de Atocha shipwreck and whose motto of “Today’s the Day” inspired people worldwide to follow their dreams. The event includes live music, a chance to win a piece of authentic treasure, live and online silent auctions, and more. Festivities kick off on Friday at 4 pm at Schooner Wharf Bar, 202 William St in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.
July 22 – 26
Hemingway Days
Key West: Writers, anglers, and fans of the late author Ernest Hemingway come together for five days of some one-of-a-kind Key West antics. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Highlights include a three-day Marlin Tournament, the raucous Hemingway® Look-Alike Contest, a Caribbean Street Fair, and the hysterical “Running of the Bulls” down Duval St. Capping it all off is the Papa’s Birthday Bash replete with cake, cocktails, and celebration at historic Sloppy Joe’s Bar, 201 Duval St. Info: 305-294-5717; keywestlookalikes.com.
COMING SOON
September 3 – 7
Just A Few Friends
Key West: Favorite Son Celebration
Key West: This 2nd annual celebration honors Key West’s favorite son, Jimmy Buffett, who passed away in 2024. Pre-Party events kick off early on W, Sept 2 with a special Jimmy Buffett Tribute Show at Comedy Key West and a Welcome Pre-Party at The Pier House’s famous Chart Room Bar. The festival officially kicks off on Th, Sept 3 with a jam-packed weekend lineup that includes foodie events, street, beach & pool parties, sailing adventures, bar strolls and more. On Su, Sep 6, you can enjoy the epic Second Line Walking Parade, which culminates with a huge party and concert on the waterfront. Come Monday, the weekend wraps up with even more activities, including the now- famous Pencil Thin Mustache Contest, an Island Tiki Sunset & Music Cruise, and a fierce bayside concert with Caymen & The Mango Men on Sunset Pier. For more info, event badges and a full list of happenings, hit up justafewfriendskeywest.com.
