What’s Up
So you’ve reached your final Florida destination, now what? Well, hold tight because this is one Florida destination where the fun never stops! In fact, there are probably more events and festivals going on in the Florida Keys & Key West than in any other Florida destination. Here’s a quick list of fun Keys’ happenings that you won’t want to miss! However be aware that due to COVID-19, we recommend that you check ahead.
Please confirm details with event organizers or venues in case of changes or cancellations.
ONGOING
Daily
Mini Golf
Ramrod Key: Come play the southernmost mini-golf course in the Florida Keys. This kid-friendly 18-hole course is a perfect family adventure. It 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) on Ramrod Key. Be sure to check out their special party packages and tournaments. Info: 305-872-4094; boondocksus.com.
Daily
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. A fun tropical theme, lush landscaping and an amazing 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 beers and you’ve got yourself a great day — not at the beach! Special event packages and tournaments, too! Open daily 10am – 10pm at Porky’s Bayside, 1410 Overseas Hwy in Marathon. Info: 305-731-7592; porkysbaysidebbq.com
Nightly
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 the Florida Bay. You can also get Happy Hour prices from 4 – 6 pm on various libations and appetizers. The nightly event is ceremoniously marked by the “Sunset Horn” bellowing just before the fiery ball disappears into the horizon. The celebration continues well after dark with live entertainment and dancing under the palms. Takes place at Snooks Bayside & Grand Tiki at MM 99.8, Southbound Lane, behind the Sandal Factory Outlet. Info: 305-453-5004; snooks.com.
Nightly
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. You can find the Lorelei Restaurant & Cabana Bar at 81925 Overseas Hwy. (MM 82, Bayside). Info: 305-664-2692; loreleicabanabar.com.
Nightly
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 pier behind the Opal Key Resort & Marina on Front Street 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 Sunset Celebration a world-famous, multicultural happening.
Nightly
Aquaplex
Key West: With three reinvented venues all under one roof, Key West’s state-of-the-art entertainment complex is where it’s all happening. This world-class dance club, with high-tech lighting and an industrial vibe, also boasts a lovely outdoor garden bar called the Back Bar as well as 22&Co, heralded as the best drag bar in the Keys. But the crowning jewel of it all is the Birdcage Cabaret featuring the world-renowned female impressionist and singer Christopher Peterson, backed by The Aquanettes, an outrageous troupe of talented drag queens who sing and dance the night away. This is THE place to go for “not-to-be-missed” entertainment. Find it all at 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, there is free admission, and everyone looks great in the golden twilight. Hugh’s View sits on the roof of The Studios of Key West. It offers panoramic vistas across the rooftops of Old Town, from the Gulf of Mexico on one side to the Atlantic on the other. Takes place from 6 – 8 pm at The Studios of Key West, 533 Eaton St. Info: tskw.org.
Every Tuesday
Farmers Market
Key Colony Beach: Stock up on all of your favorite local produce, fruits, baked goods, and more at this home town favorite outdoor market. Takes place from 9 am – 2 pm on the corner of 7th St and W Ocean Dr. Info: 305-289-1212 ext 2; keycolonybeach.net.
Every Thursday
Key West Waterfront Farmers Market
Key West: This traditional farmer’s market includes produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh bread, hot sauces, and more. You can also shop for local arts & crafts, flea market goods, jewelry, clothing/t-shirts, cigars, and CBD. It takes place from 2 pm – 7 pm at the Truman Waterfront (end of Southard St). FYI: Bring your own bags. Info: 305-731-3385; keysatisanmarket.com.
Every Saturday
Open-Air Market
Ramrod Key: Forget about driving miles to find local Florida Keys art, handmade jewelry, one-of-a-kind creations, fresh organic produce, greens, and flowers. You’ll see all that and more right at Boondocks. Takes place from 9 am – 2 pm in the parking lot of Boondocks Plaza, 27205 Overseas Hwy (MM 27.5). Info: 305-872-4094; boondocksus.com.
Every Sunday
Jazz in The Gardens
Key West: Enjoy some hot jazz amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne, and fabulous wines. Takes place from 5:30 – 8 pm at the Gardens Hotel, 526 Angela St, Key West. Info: 305-294-2661; gardenshotel.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! Takes place at 4 pm on Nov 26 and Dec 17 at the Dolphin Research Center, 58901 Overseas Hwy (MM 59 Gulfside) on Grassy Key. Info: 305-289-1121; dolphins.org.
First Friday
First Fridays on Fleming
Key West: “The Fabulous 500 Block of Fleming Street” showcases boutiques, galleries, and eateries with all kinds of cool events, including jewelry trunk shows, art openings, book signings, tastings, and libations. Takes place from 6 – 9 pm. Info:305-304-9001; Info:305-304-9001; fabflemingkw.com.
First Saturday
Market on the Green
Key West: Shop some fantastic local arts at this fun artisan market. Takes place from 10 am – 2 pm at the Sunset Green Event Lawn located between the Gates Key West Hotel and 24 Deg. North Hotel, 3852 N Roosevelt Blvd. Info: 305-400-4117; thekeyscollection.com.
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. It takes place from 9 am to noon at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.
SPECIAL EVENTS
February 13 – 14; March 13 – 14
66th Annual Key West Home Tours
Key West: One of America’s oldest and longest-running home tours showcases five lovely homes and gardens on each day’s self-guided tour. Each stop reflects the varied tastes and originality of its owners. Takes place from 1 – 4 pm. Info &tickets: 305-294-9501; OIRF.org.
February 14 – 15
20th Annual Florida Keys Seafood Festival
Key West: Local commercial fisherman pull out all of the stops during this two day feeding frenzy that celebrates our local seafood and maritime heritage. Indulge in Key West pink shrimp, succulent spiny lobster, stone crab claws, just-off-the-boat-fish preparations, and lots of landlubber options. Back dropping it all is and array of top live entertainment, local artisans and lots of immersive kids’ activities. Takes place, rain or shine, on Sa from 11 am – 8 pm; and on Su from 11 am – 8 pm at Truman Waterfront Park, 21 E Quay Rd. Info: floridakeysseafoodfestival.com.
February 21 – 22
61st Annual Key West Art & Craft Festival
Key West: This nationally recognized juried fine art show attracts over 100 fine and skilled artists from across the country and includes painters, sculptors, photographers, collage artists, and other non-functional fine arts. Takes place from 10 am – 5 pm at Truman Waterfront Park, 21 E Quay Rd. Info: 305-294-1241; keywestartcenter.com. Greater South Miami-Dade
South Miami-Dade
WEEKLY
Every Thursday – Sunday
Redland Market Village
Redland: Part flea market, part farmers market, part food emporium; this bustling marketplace is the place to shop for great bargains and fresh local produce. With almost two dozen International Food Trucks, live entertainment, and lots of fun seasonal events, visiting this 27-acre attraction is always a fun jam. Takes place on Th – F from 11am – 6 pm and on Sa & Su from 7 am – 6 pm at 24420 S Dixie Hwy. FYI: Be sure to check out the great weekend Flea Market! Info: 305-257-4335; redlandmarketvillage.com.
Every Thursday – Sunday
Wynwood Marketplace
Miami: Nestled in the heart of the Wynwood Arts District, this bustling blockbuster bazaar is home to one of Miami’s most fun (and pet-friendly) Haps. Each week, hundreds of vendors gather together in Miami’s coolest neighborhood to offer a unique selection of art, fashion, food, libations, live music, and more. The Marketplace is also home to several gourmet food trucks, pop-up eateries, craft beer and specialty cocktail bars, as well as some great entertainment and live performances. Lots of special events, too! It’s truly a unique and immersive experience. Takes place on Th from 4 pm – 3 am; Fri & Sa from Noon – 3 am; and on Su from Noon – 2 am, in Miami’s Wynwood Arts District, 2250 NW 2nd Ave, Miami, FL. Info: 305-461-2700; wynwood-marketplace.com.
SPECIAL EVENTS
November 14 – March 7
Christmas Luminosa: A World of Enchantment
Miami: You’ll see more dragons than reindeer at this fantastical, fairytale-themed lights festival, which features 40+ scenes made of silk fabric lanterns, as well as some amazing animatronic knights. Takes place from 5:30 – 9:30 pm on Su – Th; and from 5:30 – 10:30 pm on F & Sa at Jungle Island, 1111 Parrot Jungle Tr. Info: 305-400-7000; luminosamiami.com.
January 24 – 25
International Chocolate Festival
Miami: Indulge in everything chocolate during this sweet “Willy Wonka” weekend. In addition to the artisan chocolatiers, innovative dessert makers, and several tasting stations, you can also enjoy interactive workshops, live demos, and more. Takes place from 10 am – 5 pm at Fairchild Tropical Botanic Garden, 1090 Old Cutler Rd. Info: 305-667-1651; fairchildgarden.org.
January 30 – February 1
77th Annual Homestead Rodeo
Homestead: Known as the “Southernmost Rodeo” in the continental US, this annual shindig is a huge draw for top wranglers from across the country. A PCA (Professional Rodeo Cowboys Association)- sanctioned competition, the rodeo kicks off an exciting 2026 season, which boasts 600 grueling competitions. Info & tickets: homesteadrodeo.com.
OTHER FLORIDA HAPPENINGS
February 6 – 8
Artfest Fort Myers
Fort Myers: Southwest Florida’s Premier Art Festival celebrates its 25th anniversary, showcasing the works of over 200 outstanding professional artists from across the country. The weekend also includes a high school art competition, children’s craft area, sidewalk chalk extravaganza, and more. Opening Night Party kicks things off on F from 6 – 9 pm and includes a special Pops Concert. The festival continues on Sa from 10 am – 5 pm and on Su from 10 am – 4 pm at Edwards Dr and Hendry St. It takes place throughout the historic downtown area. Info: ArtFestFortMyers.com.
February 15
68th DAYTONA 500
Daytona Beach: Don’t miss the 68th running of “The Great American Race!” Historic performances, spectacular racing, unforgettable memories, and being here in person will stay with you for a lifetime. Takes place at Daytona International Speedway, at 1801 W International Speedway Blvd. Info: 800-748-7467; daytonainternationalspeedway.com.