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

Daily
Green Pineapple Key West Yoga
Key West: Whether you’re a beginner or a seasoned practitioner, this Hatha-based yoga studio offers daily classes designed for every skill level. Based on the foundations of traditional yoga practices, categories include Vinyasa, Yin, Restorative, Gentle, Breath and Mindful Movement, Pilates, and Meditation. The Green Pineapple Yoga Shala also offers workshops to feed your body, mind, and soul. Private or Group Classes are also available. Come early or stay after class for fresh juice, tea, or a super healthy Zen bite in the plant-based Wellness Cafe. Find it nestled inside The Green Pineapple Wellness Center, 1130 Duval Street, Key West. Info: 305-509-7378; greenpineapplewellness.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 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
Key West Artisan Market
Key West: Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, a wide variety of food and libations, and local musicians and authors. Takes place from 10 am – 2 pm at Higgs Beach, 1801 White St. Info: 305-731-3385; kwartisanmarket.com.

Monthly

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; kwartisanmarket.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 between the Gates Key West Hotel and 24 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

November TBD
Bacon Fest & Vendor Show
Islamorada: Take a Sunday stroll on Islamorada’s historic Old Highway, where you can shop local and regional artists and vendors and indulge in lots of tasty bacon creations. Takes place from 8am – 2pm outside the Islamorada Moose Lodge, 81573 Old Highway (MM 81) oceanside. Info: 305-664-8120.

November 13 – 17
2024 Key West Film Festival
Key West: Named one of the top 25 coolest film fests by Moviemaker magazine, this annual “must-see” event showcases films that exhibit excellence in storytelling. Enjoy screenings, visiting filmmakers, workshops, and special events at landmark venues throughout Key West. Info: keywestff.com.

November 23
Annual Light Up Key Largo!
Key Largo: For one magical night, you can ice skate in the “Diving Capital of the World” as Key Largo lights Monroe County’s tallest Christmas tree. The celebration includes an Ice Skating Rink, Santa’s Workshop, Carolers, lots of Holiday goodies, and more. Tree Lighting at 6 pm. Takes place from 4 – 8 pm at the Murray Nelson Government Center, 102050 Overseas Hwy, MM 102 Bayside. Info: 305-451-1414; keylargochamber.org.

November 27 – December 31
Key West Holiday Fest
Key West: A merry range of celebrations during Key West’s busy holiday season includes the Lighting of the Key West Bight, The Harbor Walk of Lights, Holiday Historic Inn Tours, a spectacular lighted boat parade, and lots of good cheer. Other events that you won’t want to miss: the annual hometown holiday parade, festive island lights tours on the Conch Tour Train and Old Town Trolley, seasonal artisan markets, bazaars, and multiple New Year’s Eve “drops” that spoof New York City’s annual Times Square Ball Drop. Info: keywestholidayfest.com.

November 27
Lighting of the Bight
Key West: The Key West Harbor lights up the waterfront with a dazzling display that includes a 16′ fresh pine Nautical Christmas Tree, a Fishing Buoy Tree, the original 20′ Key West Lobster Trap Tree, and a special tribute to Jimmy Buffet. Stays lit nightly through New Year’s Eve, stretching along the Key West Historic Seaport and Key West Bight Marina. Festive music starts at 5 pm, with the lighting at 6 pm. Gather on the Harbor Walk Plaza at Greene and Elizabeth St. for the best viewing. For more details on other holiday events happening in Key West, go to keywestholidayfest.com.

November 27 – December 31
Key West Harbor Walk of Lights
Key West: This “Harbor Walk of Lights” honors the maritime history of the Key West waterfront and stays lit nightly through New Year’s Eve. Stretches along the seawall past Greene, William, and Margaret Streets to the Key West Ferry Terminal. For more details on other holiday events happening in Key West, go to keywestholidayfest.com.

November 29
Black Friday Shopping Extravaganza
Key West: Find one-of-a-kind gifts, unique handmade items, exquisite art, as well as delicious culinary delights, yummy beverages, and views you won’t find at any mall. Takes place from 10 am – 6 pm along Weech Way at Truman Waterfront Park, 21 E Quay Rd. Info: 305-731-3385; keywestartisanmarket.com.

November 30
Big Pine & The Lower Keys Island Art Festival
Big Pine: This fun annual holiday event always draws a big crowd and includes live music, exhibits, arts and crafts, food vendors, and more. It takes place from 9 am to 3 pm at the Lower Keys Chamber of Commerce, MM 31, oceanside. Info: 305-872-2411; lowerkeyschamber.com.

December 1
Schooner Wharf Bar’s Annual
Tree Trimming Party & Toy Drive
Key West: Bring your nautical ornament for Schooner Wharf Bar’s big beautiful 8′ Christmas Tree or an unwrapped kids’ gift and enjoy a complimentary holiday cocktail — rum eggnog, Swedish Glog, or hot applejack. Prizes for most original, most nautical, and most popular with the crowd. Schooner Wharf’s annual Toy Drive benefits a variety of children’s organizations. FYI: Be sure to visit Santa’s Southernmost Schooner Workshop, where local artists and authors sign and sell original works for holiday gift-giving. Local musicians are also on hand playing festive holiday tunes, Reggae, and Calypso with the island sound of Steel Drums. Takes place at 6 pm at the Schooner Wharf Bar at the foot of Williams St in Key West’s Historic Seaport. Info: 305-292-3773; schoonerwharf.com.

December 5 – 8
December 13 – 15
Nutcracker Key West
Key West: Performed every other year, this Christmas spectacular is one of the largest, most elaborate stage productions ever to hit the Florida Keys and a perfect way to ring in the holidays. Set to the music of Tchaikovsky, this island interpretation of the fabled holiday ballet was written and initially produced by Key West arts patron Joyce Stahl. Elaborate costuming, national and local dancers, and an imaginative assortment of Key West icons make it a major highlight of the holiday season. Showtimes vary. Takes place at the Tennessee Williams Theater, 5901 College Road on Stock Island/Key West. Tickets: 305-295-7676; keystix.com.

December 6
20th Annual Islamorada Holiday Festival
Islamorada: A 35′ holiday tree blows magical snow at this spirited night of holiday fun, which includes a snow mountain, festive parade, community tree lighting, caroling, holiday gift bazaar, delicious food, live music, and a silent auction of masterpiece ornaments created by local artists. Takes place from 4 – 10 pm on the Great Lawn at Founders Park, MM 87, Bayside. Info: 305-664-4503; islamoradachamber.com

December 6
4th Annual Wesley House Holiday Village & BeLighted Bike Ride
Key West: This fun annual “pre-party” kicks off Key West’s annual BeLighted Bike Ride. A magical Holiday Village includes photos with Santa, community booths, games, crafts, food vendors, music, local performances, and more! The year’s event also features rides and large holiday-themed inflatable obstacle courses for the kids! Takes place from 5 – 9 pm with the festively creative “Best Bike Contest” at 7:30 pm. The BeLighted Bike Ride follows at 8pm from the Coffee Butler Amphitheater. It all takes place at Truman Waterfront Park, 21 E Quay Rd. Tickets & info: 305-809-5000; wesleyhouse.org.

December 6 & 13
Holiday Historic Inn Tours
Key West: Enjoy two enchanted self-guided tours of five different decorated inns and a sampling of holiday treats and cheer at each property. Takes place on Friday and Saturday from 6 – 8 pm. Info and tickets: 305-296-4959.

December 7
Key West Hometown Holiday Parade
Key West: The most charming hometown parade you’ll ever see, with lots of holiday floats and tons of kids of all ages. Of course, Santa will make a guest appearance! The festivities kick off at 7 pm on Truman Ave at White St. The parade then proceeds down to Duval and ends at Eaton. Info: 305-809-3881; keywesthistoricseaport.com.

December 8
Eaton Street Christmas Stroll
Key West: Keys Choral Arts presents a short program of sacred and secular music for this festive season at 3:30 pm at St Paul’s Episcopal Church, 401 Duval St. Group Stroll follows at 4 pm along Eaton Street in Old Town. Info: stpaulskeywest.org

December 8
Annual Holiday Tree Lighting
Key Colony Beach: Wear your ugliest Christmas sweater and high-tail it over to the annual lighting of Key Colony’s giant Christmas Tree “Under the Tiki.” Make a donation to “Presents in Paradise” and add an ornament to the tree. There is lots of egg nog and hot chocolate to get you into the spirit, live music, a 50/50 raffle, food, drinks, and a visit from Santa himself. Kicks off at 5 pm with a tree lighting at 7 pm at Havana Jack’s Oceanside, 401 E Ocean Dr, Key Colony Beach. Info: 305-743-4849; HavanaJacksOceanside.com.

December 8
Eaton Street Holiday Stroll at The Studios of Key West
Key West: During this holiday tradition on Eaton Street, neighborhood venues host short Christmas-themed performances. At The Studios of Key West, you can sip on Christmas cocktails on the rooftop of Hugh’s View and do some holiday shopping at the Member’s Show, displayed throughout all four gallery spaces. It takes place from 3:30 pm to 7:30 pm at The Studios of Key West, 533 Eaton St. Info: tskw.org.

December 13
8th Annual Holiday Concert & Bazaar
Key West: One of Key West’s most popular holiday celebrations boasts some of the island’s finest artisans, musicians, and choirs; lots of great food, eggnog, and other festive libations, as well as a holiday light show projected on the face of the Custom House. You’ll also have an opportunity to shop for lots of unique gifts, including handcrafted jewelry, clothing, textiles, home decor, and more. FYI: Santa will be on hand for last-minute requests and “selfie” photos. Takes place from 5 – 9 pm on the historic porch of the Custom House and spills out onto the street in front of the Museum at 281 Front St. Info and tickets: 305-295-6616; kwahs.org.

December 14
Schooner Wharf Bar Lighted Boat Parade
Key West: A magical nautical display of lights and creativity is the hallmark of this enormous holiday maritime event in Key West’s Historic Seaport. The boats come very close to the docks of the Schooner Wharf Bar, where the Judge’s Stand is located, which makes it a great vantage point. Festivities kick off at 6 pm; the parade starts at 8 pm, followed by a big Awards Party at Schooner Wharf Bar, located at the foot of William St. Info: 305-292-3773; schoonerwharf.com.

December 14
Key Largo Lighted Boat Parade
Key Largo: The waters of Blackwater Sound in Key Largo shimmer as decorated boats put on “A Cartoon Christmas” along the shoreline to celebrate the holiday season. Boats line up at 6:30; the parade kicks off at 7:30 pm. The top spots for viewing are between MM 103 and 104. Info: 305-451-4502; keylargoboatparade.com.

December 14
Boot Key Harbor Lighted Boat Parade
Marathon: Marathon gets all decked out with their own festive Lighted Boat Parade. It sets sail at 6 pm from the West end of Boot Key Harbor (7 Mile Bridge side) and slowly winds its way east into the harbor towards Sombrero Marina Dockside. The parade continues until 8 pm. Best views include the Marathon Marina, Lazy Days South, Burdines, and Dockside Lounge.

December 15
Key Colony Beach Lighted Boat Parade
Key Colony Beach: Key Colony’s Lighted Boat Parade shoves off at 6 pm from the 7th Street Canal and makes three passes by the Judges’ Stand before heading up and down the 8th – 12th Street canals. Info: 305-743-7214; kcbca.org

December 15 – 30
Waterfront Winter Wonderland
Key West: Coffee Butler Amphitheater transforms into an amazing winter wonderland with ice skating, rides, games, music, holiday lights, a vendor village with food and local artisans, and more. Takes place at Truman Waterfront Park, 21 Quay Rd.

December 25
Christmas Day Brunch Sail
Key West: Dreaming of a crystal clear, blue Christmas? Then, spend Christmas morning aboard the Schooner America 2.0 for a brunch sail that you’ll never forget! This two-hour sail includes a fully catered brunch starting with complimentary Mimosas and Bloody Marys or champagne. Departs from Key West’s Historic Seaport. Info & tickets: 305-292-7245; sail-keywest.com.

December 27 – December 28
Annual Key West Home Tours
Key West: Festively dressed Key West homes and gardens take center stage during this much anticipated annual event, which showcases exquisite restorations, creative renovations, and delightful interiors and exteriors. The self-guided tours take place from 1 – 4 pm and benefit the Old Island Restoration Foundation. Info: 305-294-9501; Tickets & schedules at OIRF.org.

December 31
New Year’s Eve Fireworks on Blackwater Sound
Key Largo: The Back Bay is the setting for the annual midnight New Year’s Eve fireworks extravaganza that’s set to live music performed at Sundowners, MM 104 bayside. Info: 305-664-4651.

December 31
New Year’s Eve Celebrations in Key West
Key West: Ring in 2025 with a “Conch Shell Drop” at Sloppy Joe’s Bar, 201 Duval St; the descent of a super-sized red high-heel shoe (replete with a renowned local female impersonator) at the Bourbon St Pub/New Orleans House Complex, 724 Duval St; a big New Year’s Eve Bash at the Schooner Wharf Bar, 202 William St; and a massive replica of a Key lime wedge splashing down into a larger-than-life margarita glass at Ocean Key Resort & Spa, 0 Duval St.

December 31
New Year’s Eve at Cheeca Lodge & Spa
Islamorada: This ultra-chic beachside resort hosts a midnight fireworks display over the Atlantic Ocean with tasty libations and live music. Takes place at Cheeca Lodge & Spa at MM 82 oceanside. Info: 305-664-4651; cheeca.com.

January 11 – 12
Annual Florida Keys Celtic Festival
Marathon: Break out your kilts and dancing shoes because this festive Gaelic celebration will have you kicking up your heels. Enjoy top acts by international Celtic bands, Celtic food and beer, Highland Athletics, a Children’s Glen, and a Celtic Marketplace. The festival begins on Sa from 10 am – 7 pm and on Su from 11 am – 5 pm at Marathon Community Park, MM 49. Tickets & info: 305-743-6412; floridakeyscelticfestival.com.

January 24 – 25
Annual Key West Home Tours
Key West: Festively dressed Key West homes and gardens take center stage during this much anticipated annual event, which showcases exquisite restorations, creative renovations, and delightful interiors and exteriors. The self-guided tours take place from 1 – 4 pm and benefit the Old Island Restoration Foundation. Info: 305-294-9501; Tickets & schedules at OIRF.org

January 25 – 26
21st Annual Big Pine & Lower Keys Nautical Expo
Big Pine: Get great deals on all things nautical and local arts and crafts, clothing, and jewelry. Live music, food, and beverages, too. Free admission and parking. Takes place on Sa from 8 am – 4 pm and on Su from 8 am – 2 pm at the Lower Keys Chamber, MM31, Oceanside grounds. Info: 305-872-2411; lowerkeyschamber.com.

January 26
Annual Schooner Wharf Wrecker’s Cup Race
Key West: This is the first leg of the spirited 7-mile race to Sand Key, where bragging rights are the top prize. The race kicks off at 1pm with an Awards Ceremony at 7 pm. Takes place at Schooner Wharf Bar in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.

January 26
Wrecker’s Race Aboard Schooner America 2.0
Key West: If you really want to enjoy the thrill of the Wrecker’s Cup Race, then climb aboard the fastest schooner in Key West: Schooner America 2.0. It starts at 1 pm with their firing of the cannon. Tickets include a round of beer, wine, champagne, and a boxed lunch. Info & tickets: 305-292-7245; sail-keywest.com.

Coming Soon

February 14 – 15
March 14 – 15
Annual Key West Home Tours
Key West: Festively dressed Key West homes and gardens take center stage during this much anticipated annual event, which showcases exquisite restorations, creative renovations, and delightful interiors and exteriors. The self-guided tours take place from 1 – 4 pm and benefit the Old Island Restoration Foundation. Info: 305-294-9501; Tickets & schedules at OIRF.org.

February 15 – 16
19th Annual Florida Seafood Festival
Key West: Lots going on for adults and kids, from feasting on fresh local seafood and shopping for marine-related crafts to face-painting, kids’ hands-on activities, raffles, and live music. Takes place on Sa from 11am – 8 pm and on Su from 11 am – 5 pm in Bay View Park at 1320 Truman Ave. Info: 305-619-0039; floridakeysseafoodfestival.com

February 22 – 23
60th 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 to 5 pm along the Quay at Truman Waterfront Park, 100 Southard St. Info: 305-294-1243; keywestartcenter.com.

Other Florida Happenings

January 25 – 26
Hoggetowne Medieval Faire
Gainesville: For one magical weekend, Depot Park transforms into “Hoggetowne” — a medieval marketplace where you can immerse yourself in the rich culture of the Middle Ages. A bastion of medieval revelry, this fantastical Faire showcases Olde World demonstrations and breathtaking staged combat shows, as well as Medieval music and dance, a living chessboard, royal knighting ceremonies, feasting on turkey legs and lots more! Takes place, rain or shine, from 10 am – 6 pm at Depot Park, 874 SE 4th Street in Gainesville. Tickets & info: 352-334-5084; HoggetowneMedFaire.com.

January 23 – 26
The 63rd Rolex 24 At DAYTONA Weekend
Daytona Beach: From sunrise to sunset and all through the night, witness North America’s most prestigious sports car race in this twice-around-the-clock marathon that kicks off the IMSA WeatherTech SportsCar Championship season. The Rolex 24 also features a pre-race grid and garage access, the famous Ferris wheel and fireworks, autograph sessions, live entertainment, and displays from the top manufacturers. Takes place at Daytona International Speedway, the “World Center of Racing” at 1801 W International Speedway Blvd. Info: 800-748-7467; daytonainternationalspeedway.com.

January 31 – February 2
Artfest Fort Myers
Historic Downtown Fort Myers: Southwest Florida’s Premier Art Festival celebrates its 25th anniversary on the spectacular downtown waterfront and showcases the works of 200+ outstanding professional artists from across the country. Also includes a high school art competition, children’s craft area, sidewalk chalk extravaganza and yummy food and beverage. Plenty of parking and trolley service. Opening Night Party kicks things off on F from 6 – 9 pm and includes a special Pops Concert; The weekend-long festival continues on Sa from 10 am – 5 pm and on Su from from 10 am – 4 pm at Edwards Dr and Hendry St. Get lots of extra perks when you sign up for VIP Club tickets. More info at ArtFestFortMyers.com.