Festivals, Flavor & Tons of Island Fun - The Florida Keys & Key West Signature Events for 2026
FLORIDA KEYS (December 16, 2025) – Sun-soaked days, toasty tropical breezes, and a year-round lineup of unique offerings await curious travelers in the Florida Keys & Key West. From funky festivals and mouthwatering culinary events to quirky island traditions you won’t find anywhere else, this destination blends full-on festive with tons of flavor 365 days a year. Welcome to America’s southernmost island...where creativity thrives, community shines, and every moment is delivered with a dash of Florida Keys magic. Ready to turn up the adrenaline on your social schedule? You’ve come to the right place. Here’s what’s on tap for 2026:
CULTURE, MUSIC & ISLAND VIBES
Key West Literary Seminar — January
www.kwls.org
Start the year with stories by the sea. The Key West Literary Seminar brings renowned authors and passionate readers together for four days of readings, workshops, and literary magic in the island that inspired Ernest Hemingway and Tennessee Williams. (January 8-11, 2026)
Florida Keys Celtic Festival — January
www.floridakeyscelticfestial.com
A family-friendly celebration of Celtic music and culture featuring Celtic rock and traditional Irish and Scottish music, dancing, food and highland athletics. (January 10-11, 2026)
Mile 0 Fest — January
www.mile0fest.com
Texas Red Dirt meets turquoise water at Mile 0 Fest, a five-day blend of Americana music, beachfront stages, live music sails, and the kind of sunsets musicians write songs about. (January 27-31, 2026)
Presidential Families Weekend – February
www.trumanlittlewhitehouse.org
Join descendants of U.S. presidents during Presidents Day weekend as they share stories about their relatives’ service as Presidents of the United Sates. (February 14-16, 2026)
Gigantic Nautical Market — February
www.rotarynauticalmarket.com
This huge outdoor market, boat show and food truck rally takes place throughout the expansive Founders Park in Islamorada. (February 21-22, 2026)
Island Fest — March
www.islamoradachamber.com/island-fest
Islamorada’s annual juried art fest along with live music, great food, classic cars and live entertainment. (March 28-29, 2026)
Key West Songwriters Festival — April/May
www.keywestsongwritersfestival.com
The world’s biggest songwriter festival spreads across 30+ venues — from boats to beach bars — giving fans a front-row seat to the stories behind the songs. Past performers include stars like Kacey Musgraves and Florida Georgia Line. (April 29 – May 3, 2026)
Key West Pride — June
www.gaykeywestfl.com/pride
Celebrate love, joy, and Key West’s famous “One Human Family” spirit with a week of drag shows, pool parties, comedy nights, and the dazzling Pride Parade featuring the island’s giant Sea-to-Sea rainbow flag. (June 3-7, 2026)
Hemingway Days — July
www.hemingwaydays.com
With Hemingway look-alike contests, a ‘Running of the Bulls’ (the Key West version!), marlin fishing, and birthday bashes, Hemingway Days honors the legendary author’s bold, mischievous spirit with five days of fun. (July 22-26, 2026)
Womenfest — September
www.gaykeywestfl.com/womenfest
One of the world’s premiere LGBTQ+ celebrations for women, Womenfest brings sun, sea, themed parties, and empowering connection to the island known for its warm, welcoming vibes. (September 2-6, 2026)
REEF Fest — October
www.reef.org/REEFfest
Divers, snorkelers and ocean lovers unite at REEF Fest in Key Largo to celebrate their love of marine life and learn about the latest in conservation, with plenty of time for Florida Keys adventures that bring those lessons to life! (October 15-18, 2026)
Key West Film Festival — November
www.keywestff.com
Lights, camera, island action! With screenings at historic theaters and breezy outdoor venues, the Key West Film Festival showcases standout films, documentaries, shorts, and Florida talent. (November 11-15, 2026)
FOOD & DRINK EVENTS: A TASTE OF THE TROPICS:
Key West Food & Wine Festival — January/February
www.keywestfoodandwinefestival.com
Celebrate food and wines from the Pacific Coast in tropical Key West settings including the Grand Tasting at Audubon House and Tropical Gardens. (January 28-Feb 1, 2026)
Marathon Seafood Festival — March
www.marathonseafoodfestival.com
Find fabulous fresh seafood, live entertainment and family fun at this annual festival at Marathon Community Park. (March 14-15, 2026)
Key Lime Festival — July
www.keylimefestival.com
Meet Key West’s zestiest celebration. Expect pie tastings, cocktail competitions, the famous Pie Drop from the lighthouse, and the Key Lime Pie Eating Championship, all with a tart tropical twist. (July 1-5, 2026)
Key West Lobsterfest — August
www.keywestlobsterfest.com
Commemorate the opening of the Florida Spiny Lobster season with an island-wide party. From the savory kickoff Lobster Boil to the massive Duval Street Fair with live music, this is the ultimate crustacean celebration. (August 5-9, 2026)
Rum Fest Key West — August
www.rumfestkeywest.com
Sip, savor, and celebrate Caribbean culture with premium rum tastings, a Rum Cake Competition, Ti Punch Brunch, and even optional Day Trips to Cuba. (August 12-16, 2026)
Key West BrewFest — September
www.keywestbrewfest.beer
Cheers from the shoreline! Over Labor Day Weekend, enjoy more than 225 craft beers at beachside tastings, pool parties, and flavorful pairing events. (September 5-7, 2026)
Taste the Keys — October
www.tastethekeys.com
The month-long culinary celebration of the Upper Keys returns with prix-fixe menus, Foodie Trolley Tours, chef showdowns, and dreamy beachfront dinners. (October 1-31, 2026)
ADVENTURE & SPORTS IN PARADISE
Seven Mile Bridge Run — April
www.7mbrun.com
Run above the sea on one of the most scenic races in the world, a 6.8-mile journey over brilliant blue water supporting local youth athletics. (April 11, 2026)
Florida Keys Lionfish Derby — April
https://www.reef.org/derby
Hosted by Reef Environmental Education Foundation (REEF), this hands-on conservation event invites divers and snorkelers to help remove invasive lionfish from Keys waters. (April 23-26, 2026)
KEYS100 Ultramarathon — May
www.keys100.com
For the truly adventurous: 100 miles from Key Largo to Key West (plus 50-mile and 50K options), finishing steps from the sand at Higgs Beach. (May 16-17, 2026)
Key Largo Triathlon — August
www.trisignup.com
This Key Largo race sanctioned by USA Triathlon takes place at John Pennekamp Coral Reef State Park and surrounding areas in Key Largo. (August 16, 2026)
Swim for Alligator Lighthouse — September
www.swimalligatorlight.com
Swimmers take on an eight-mile open-water challenge to an offshore lighthouse and back, all to support reef conservation. (September 10-12, 2026)
Race World Offshore Key West World Championship — November
www.raceworldoffshore.com/key-west
High-speed, heart-thumping offshore powerboat racing electrifies Key West with the sport’s biggest teams and boldest maneuvers. (November 6-13, 2026)
First State Bank Key Largo Bridge Run — December
www.keylargobridgerun.com
Challenge your best time in the 15th Annual First State Bank Key Largo Bridge Run. Run or walk our bridge on the 18-mile stretch, "The Gate Way to the Keys"! It's an awesome course, flat and fast with one big challenging bridge, Jewfish Creek Bridge, and gorgeous views of the Florida Bay and Barnes Sound. (2026 dates: TBD)
Key West Triathlon — December
www.keywesttriathlon.com
A “tri-cation” favorite, this event mixes competition with vacation, offering multiple race distances along Key West’s sparkling shoreline. (2026 dates: TBD)
ICONIC, QUIRKY & TOTALLY UNIQUE: ONLY IN THE KEYS
Conch Shell Blowing Contest — March
www.oirf.org/our-events
A Key West tradition for more than 60 years, the “Conch Honk,” sees contestants of all ages tried their best to make beautiful (or sometimes not-so-beautiful) sounds with the iconic conch shell. (March 7, 2026)
Conch Republic Independence Celebration — April
www.conchrepublic.com
Relive Key West’s tongue-in-cheek secession with a week of irreverent fun, including the Great Sea Battle, the World’s Longest Parade, and the Schooner Wharf Wreckers Cup Race. (April 17-26, 2026)
Coralpalooza — June
www.coralrestoration.org/coralpalooza
Divers from across the globe join the Coral Restoration Foundation® for reef restoration dives during this internationally recognized ocean conservation event. (June 7, 2026)
Underwater Music Festival — July
www.lowerkeyschamber.com/product/underwater-music-festival
Grab your fins and a snorkel for a whimsical underwater concert at Looe Key Reef, complete with “sea creature” costumes and coral-friendly messaging. (2026 dates: TBD)
Fantasy Fest — October
www.fantasyfest.com
Key West’s legendary 10-day costume extravaganza celebrates creativity with themed parties, Tutu Tuesday, the Zombie Bike Ride, and a spectacular parade that lights up the island. (October 16-25, 2026)
New Year’s Eve Red Shoe Drop — December
www.visitfloridakeys.com
Ring in the new year Key West–style as a local drag queen descends from the sky in a giant red high heel, a fabulously tropical twist on the Times Square ball drop. (December 31, 2026)
WORLD-CLASS FISHING TOURNAMENTS
Ladies, Let’s Go Fishing! Islamorada Women’s Sailfish Tournament —January/February
www.ladiesletsgofishing.com
Perfect for beginners, this supportive weekend blends hands-on learning, friendly competition, and the unbeatable thrill of fishing in the Florida Keys. (January 30 – February 1, 2026)
Marathon Premiere Sailfish Tournament — April
www.marathonsailfish.com
This competitive fishing tournament is also a non-profit supporting fishing and recreational opportunities for disadvantaged children. (April 17-18, 2026)
Marathon Offshore Bull and Cow Dolphin Tournament — May
www.marathonoffshoretournament.com
This competitive tournament pays a guaranteed $20,000 for the largest bull and cow dolphin combined weight – or $30,000 with 100 or more boat entered. (May 1-3, 2026)
Key West Marlin Tournament — July
www.keywestmarlin.com
Fish the waters Hemingway loved while teams compete for $50,000 in prizes chasing marlin, spearfish, and fun-fish species. (2026 dates: TBD)
Take Stock in Children Backcountry Challenge — September
www.keylargorotary.org
Anglers fish around the clock from Friday night to Sunday afternoon in search of seatrout, snook and redfish in this annual contest that supports scholarships. (September 25-27, 2026)
Sugarloaf Showdown – November
www.sugarloafshowdown.com
Anglers vie for awards in multiple divisions including fly, spin and youth while targeting bonefish, permit and barracuda. (November 12-14, 2026)
High-resolution images, photo credits, and captions are available at this link.
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Female impersonator Randy Roberts hangs in a giant replica of a woman's red high-heel shoe over Duval Street late Tuesday, Dec. 31, 2024, at the Bourbon St. Pub complex in Key West, Fla. The Red Shoe Drop, a Key West New Year's Eve tradition, is one of several Florida Keys warm-weather takeoffs on New York City's Times Square ball drop marking the arrival of the new year. (Andy Newman/Florida Keys News Bureau)
Competitors in the Seven Mile Bridge Run make their way across the longest of 42 bridges over water that help to comprise the Florida Keys Overseas Highway Saturday, April 13, 2024, in Marathon, Fla. The annual race attracted 1,500 participants. Collin Wainwright, 28, of Philadelphia, Penn., was first across the finish line with a time of 40 minutes and 33 seconds and also claimed the top spot in the overall men’s division. Joanna Stephens, 29, of Dallas, Ga., repeated as overall women’s winner finishing in 43:13. (Andy Newman/Florida Keys News Bureau)
Competitors in the Seven Mile Bridge Run make their way across the longest of 42 bridges over water that help to comprise the Florida Keys Overseas Highway Saturday, April 13, 2024, in Marathon, Fla. The annual race attracted 1,500 participants. Collin Wainwright, 28, of Philadelphia, Penn., was first across the finish line with a time of 40 minutes and 33 seconds and also claimed the top spot in the overall men’s division. Joanna Stephens, 29, of Dallas, Ga., repeated as overall women’s winner finishing in 43:13. (Andy Newman/Florida Keys News Bureau)
Halfway home: swimmers round the historic Alligator Reef Lighthouse during the 2025 Swim for Alligator Lighthouse in Islamorada in the Florida Keys on Saturday, September 13, 2025. The 8-mile open-water race draws hundreds of athletes each year to test their endurance while raising funds to preserve the 152-year-old landmark. (Christjen Johnson/Florida Keys News Bureau).
Kayak support teams guide swimmers around the base of the historic Alligator Reef Lighthouse during the 2025 Swim for Alligator Lighthouse in Islamorada in the Florida Keys on Saturday, September 13, 2025. More than 300 athletes competed in the grueling 8-mile open-water race, which raises funds to preserve the 152-year-old lighthouse and provide scholarships. (Steve Panariello/Florida Keys News Bureau).
A group of creatively costumed divers hits all the right notes at this makeshift concert on Looe Key Reef in the Florida Keys during the Underwater Music Festival on July 12, 2025. (Front row from left, Donna Whitney, Kristen Livengood. Back row from left, Jason Samuse, Ricky Allen and Monroe County Commissioner, Holly Merrill Raschien.) Frazier Nivens/Florida Keys News Bureau)
Hemingway Look-Alike Winner, Tim Stockwell of Key West, Florida, celebrates his victory with a group of past winners. The contest took place in Key West on July 26, 2025, at Sloppy Joe’s Bar, a frequent hangout of Ernest Hemingway. (Mark Hedden/Florida Keys News Bureau)
On your mark! Hundreds of Hemingway Look-Alikes pack Duval Street in Key West, Florida, on Saturday, July 26, 2026, for the city’s 44th Annual Running of the Bulls. The event, a spoof on the real running of the bulls in Pamplona, Spain, pays homage to legendary author Ernest Hemingway, who ran with the real bulls in Spain. Ownby has joined in the fun of the Hemingway Days Festival for the past 10 years and is a semi-finalist in the final round of the Hemingway Look-Alike contest. (Mark Hedden/Florida Keys News Bureau).
A sailfish explodes from the water off Islamorada, showcasing the acrobatic power that draws anglers to the Ladies, Let's Go Fishing! Islamorada Women's Sailfish Tournament, Jan. 30-Feb. 1, 2026. The tournament welcomes beginners and experienced anglers alike in a supportive weekend of hands-on learning, friendly competition and conservation, with all sailfish released. Women compete for top angler and team honors while fishing from their own boats or charters in the waters off Islamorada, known as the sportfishing capital of the world. (Andy Newman/Florida Keys News Bureau)
Goggles. Check! This accessory wasn’t just for fashion. Beth of Wheaton, Illinois (right), and Camryn of Magnolia, Texas, (left), sported them to compete in the Key Lime Pie Eating Championship in Key West, Fla., on July 4, 2025. The contestants dove head-first into Florida’s most iconic dessert in the messy, hands-free contest that headlines the annual Key Lime Festival, running through Sunday, July 6. (Mark Hedden/Florida Keys News Bureau).
Audience members listen as, from left, author Dani Shapiro and Key West Literary Seminar Executive Director Arlo Haskell discuss Shapiro’s memoir Inheritance during the “Inheritance and Family Secrets” session at the 2025 Key West Literary Seminar, held Jan. 9–12 at the San Carlos Institute in Key West, Fla. Shapiro reflected on identity, truth, and family revelations in the digital age. (Nick Doll/Key West Literary Seminar)
Performers costumed as oceanic sirens smile for the crowd during Saturday night’s Deep Eddy Vodka Fantasy Fest Parade in Key West, Fla., Oct. 25, 2025. The pair were part of the “Sirens & Sea Monsters” entry, which transformed Duval Street into an underwater dreamscape for this year’s “Bedtime Stories and Magical Monsters”–themed celebration. The procession marked the finale of the island city’s 10-day costuming festival. (Mark Hedden/Florida Keys News Bureau)
Factory Stock-class boats surge off the starting line Friday, Nov. 7, 2025, during the Race World Offshore Key West World Championship in Key West, Fla. Say Less MF (21, foreground) finished second in Friday’s race and is tied with GC Racing MTI at 205 points heading into Sunday’s championship finale. (Bert Budde/Florida Keys News Bureau)
Platinum-selling country music duo, LOCASH entertains throngs of music lovers packed onto Duval Street in Key West, Fla., on May 3, 2025. The free concert was part of the 29th Annual Key West Songwriters Festival. (Larry Blackburn/Florida Keys News Bureau)
Music fans got a double dose of satisfaction with this brilliant backdrop at the 29th Annual Key West Songwriters Festival kickoff concert. Hundreds of fans swayed to the music written by emerging artists on Ocean Key’s Sunset Pier in Key West, Fla., on April 30, 2025. (Mark Hedden/Florida Keys News Bureau)
A wood-fired Neapolitan pizza fresh from the oven at Italian Food Company draws smiles during the Taste the Keys trolley tour Sept. 2 in Key Largo. The progressive dining experience took participants to multiple Upper Keys restaurants, offering chef-curated small plates and paired beverages that showcased the region's culinary diversity. (Doug Finger/Florida Keys News Bureau)
ABOUT THE FLORIDA KEYS & KEY WEST
The Florida Keys & Key West is a premier getaway destination located at the southernmost tip of Florida and the continental United States. The Keys stretch over 125 miles connected by 42 bridges and bordered by the Atlantic Ocean and the Gulf. Discover the spectacular array of diverse activities offered in the Florida Keys like fishing, diving, natural wonders, fine dining and cultural heritage. From large resorts, secluded waterfront hideaways and courtyard guest houses, visitors can uncover the perfect place for their vacation. Restoration, renovation and preservation have become a way of life in the Florida Keys. Whether you’re driving or flying into the Keys, one thing is for sure: there’s simply no place quite like it. Want more reasons to visit The Florida Keys & Key West? Get inspired at visitfloridakeys.com and follow us @thefloridakeys on social media.
MEDIA CONTACTS
Mary B. Haban
Senior Director of Public Relations
Visit Florida Keys & Key West
(305) 394-3142
Visit Florida Keys & Key West PR Agency Team (TURNER)