Florida Keys Pack the Fall Calendar with Festivals, Flavors and Fun
Signature Events and Island Traditions Unfold from Key Largo to Key West
FLORIDA KEYS & KEY WEST, Fla. (September 8, 2026) - Ditch your sweater and break out the flip-flops. Fall in the Florida Keys & Key West means warm days, island vibes and a calendar packed with events you just won’t find anywhere else. Swim eight miles through open water. Play a round of golf by boat. Savor the flavors of the Upper Keys. Or head to Key West for the roar of powerboats and the colorful, anything-goes spirit of Fantasy Fest. From September through November, fall in the Florida Keys is less about changing leaves and more about changing your latitude.
And this fall comes with a little extra value. A new initiative from Visit Florida Keys & Key West offers deals and savings across the island chain. Through Oct. 31st, Keys Season spotlights a variety of lodging partners, restaurants, watersports operators and attractions with value offerings. Learn more at VisitFloridaKeys.com/KeysSeason.
Why visit The Florida Keys & Key West this fall?
- Great Weather – Warm days, balmy breezes and comfortable temperatures set the stage for effortless exploring.
- Award-Winning Dining – MICHELIN recognition of two Key West restaurants adds a new distinction to the culinary scene, earning praise for its fresh seafood, inventive chefs and mouthwatering local flavors.
- Stone Crab Season – Stone crab season kicks off Oct. 15, bringing sweet, locally harvested claws to plates and palates from Key Largo to Key West.
- Outdoor Adventures – Milder temperatures make fall ideal for snorkeling, boating and biking.
- World-Class Fishing – Fall brings excellent opportunities for anglers to catch a variety of prized game fish in the waters surrounding the Florida Keys. From sailfish to bonefish, permit, tarpon, snook and redfish, the opportunities are endless.
- Added Value – Keys Season brings extra perks to maximize your stay through Oct. 31.
Fall also brings an array of events and experiences to the Florida Keys & Key West, including:
Swim for Alligator Lighthouse
Sept. 12 | Islamorada, Fla. Adventure seekers take on one of the Florida Keys' most iconic athletic challenges during the eight-mile Swim for Alligator Lighthouse. This is tropical open-water swimming at its purest, drawing participants from around the world for the challenging journey to the historic offshore lighthouse and back. Swimmers compete individually or as part of two-, three- or four-person teams, with kayakers providing support along the course. Learn more.
Conch Scramble Charity Golf Tournament
Sept. 25 - 26 | Islamorada, Fla. Only in the Florida Keys can a golf tournament swap out golf carts for boats. The unique, island-style experience brings the bravado with floating greens, foursomes traveling by boat and biodegradable golf balls. Creative costumes, decorated boats, along with food, festivities and awards add to a day where watching the fun unfold is even better than being in the tournament. Learn more.
Lower Keys Fall Migration Mania Birding & Nature Adventure
Sept. 27 | Lower Keys, Fla. At the Key West Tropical Forest & Botanical Garden, birders, butterfly enthusiasts, and nature lovers can explore one of the Lower Keys' premier wildlife habitats during the peak of fall migration. The day includes early access to the Garden, self-guided exploration, and optional guided birding and butterfly tours led by local experts. Learn more.
Taste the Keys
Oct.1 - 31 | Upper Keys / Key Largo, Fla. Savor the flavors of paradise during Taste the Keys, a month-long culinary celebration showcasing the restaurants, chefs and culinary creativity of Key Largo and the Upper Keys. Throughout October, participating restaurants offer specially pricedprix-fixed menus inspired by local ingredients and island culture. Visitors will also enjoy signature dining experiences, chef-led events, trolley tours featuring tastings and cocktails, and the Signature Dish Showdown, where diners vote for their favorite culinary creation. The celebration is timed perfectly with Keys Season savings across the Upper Keys. Learn more.
Celebrate Sunset on the Old Seven Mile Bridge
Oct. 10 | Marathon, Fla. Celebrate America’s 250th birthday with a spectacular sunset gathering at the historic Seven Mile Bridge. This uniquely Florida Keys event will bring residents and visitors together for an evening of local food, live music, history, culture, and community spirit, featuring culinary creations from the Marathon High School Culinary Program alongside fresh offerings from Grimal Grove. Learn more.
SOMO Half Marathon & 10K
Oct. 11 | Key West, Fla. Runners and walkers are invited to experience the Conch Republic with a scenic race route along the waterfront. Whether chasing a personal best or a slice of Key lime pie after crossing the finish line, this tropical race offers breathtaking island views and a festive atmosphere that make it a bucket-list event for athletes and vacationers alike. Learn more.
REEF Fest
Oct. 15 - 18 | Key Largo, Fla. REEF Fest is a must-attend gathering for anyone who loves the ocean and all its creatures. The eco-conscious festival combines educational marine conservation programming with immersive outdoor adventures, social events and opportunities to connect with the underwater world that makes the Florida Keys a globally renowned destination for reef exploration. Learn more.
Fantasy Fest
Oct. 16 - 25 | Key West, Fla. For more than four decades, Fantasy Fest has transformed Key West into a colorful hub of self-expression and island spirit. The world-famous, 10-day extravaganza features more than 60 events, including themed parties, masquerade balls, art walks, street fairs and the spectacular Fantasy Fest Parade along Duval Street. From the Zombie Bike Ride and Pet Masquerade to the Royal Coronation Ball and Goombay Festival, Fantasy Fest offers a one-of-a-kind cultural experience where imagination takes center stage. Learn more.
Trop Rock'N Duval
Oct. 28 - Nov. 1 | Key West, Fla. Island music fans can experience five unforgettable days of live performances during Trop Rock'N Duval. More than 60 artists perform across 23Key West venues, creating a walkable, island-wide celebration of the sounds inspired by life on the water. With intimate bar performances, sunset sessions, sold-out theater shows and sing-along favorites, this annual event captures the welcoming spirit that defines Key West. Learn more.
Race World Offshore Key West World Championship
Nov. 1 - 8 | Key West, Fla. The waters surrounding Key West become a high-speed playground during the Race World Offshore Key West World Championship. As the season finale of offshore powerboat racing, the event attracts elite teams from around the world for a thrilling showcase of innovation, teamwork and raw horsepower. Learn more.
9/11 Exhibit, Army Knights and Drone Shows
November 18 & 20| Islamorada & Big Pine Key, Fla. America’s 250th celebration continues across the Florida Keys this November with a powerful mix of remembrance, patriotism and only-in-the-Keys moments. Experience the Tunnel to Towers “Never Forget” traveling 9/11 exhibit, look to the skies for a U.S. Army Knights paratrooper drop-in and catch a spectacular drone show Nov. 18 at Founders Park in Islamorada. The celebration continues Nov. 20 at Big Pine Key Community Park with an evening of patriotic programming, followed by a 5K run the next day. Learn more.
Key West Film Festival
Nov. 18 - 22 | Key West, Fla. Named one of MovieMaker Magazine's “25 Coolest Film Festivals in the World,” the Key West Film Festival brings cinematic excellence to paradise. The five-day event features premieres, filmmaker discussions, documentaries, feature films, student shorts, critics panels and awards presentations, all set against Key West's historic architecture, tropical beauty and vibrant arts scene. Learn more.
Tour de Keys
Nov. 21 | Key Largo/Islamorada/Marathon/Lower Keys/Key West, Fla. Join riders from across the country for a stunning charity ride from either Key Largo (100 miles) or Marathon (50 miles) to Key West. Tour de Keys is a journey through paradise with purpose, benefitting MARC House, a Monroe County organization that supports adults with developmental disabilities. Learn more.
FISHING EVENTS
Anglers of all skill levels can join in at these fall tournaments.
Herman Lucerne Memorial Backcountry Fishing Championship
Sept. 18 - 20 | Islamorada, Fla. Honoring “Mr. Everglades” himself, this tournament challenges anglers to catch seven specific species within Everglades National Park waters. Learn more.
Take Stock in Children Backcountry Challenge
Sept. 25 - 27 | Key Largo, Fla. This catch-and-release tournament in Key Largo focuses on trout, snook, and redfish, all to support local vocational programs and scholarships for Upper Keys youth. Learn more.
IGFA Permit Invitational
Sept. 29 - Oct. 2 | Lower Keys, Fla. This premier tournament celebrates world-class inshore game fish, the sport of fly fishing, the ethics and the programs of the International Game Fish Association. Learn more.
Backcountry Fly Championship Series
Oct. 2 - 3 | Islamorada, Fla. Compete to catch the most inches of snook and redfish in a challenge where one-inch equals one point. Learn more.
Casting for Cats Backcountry Tournament
Oct. 16 - 17 | Islamorada, Fla. This formerly all-female tournament is now open to everyone, with a co-ed division and a new junior division. The event is a major fundraiser to help control the feral cat population in the Upper Keys. Learn more.
“Ladies, Let’s Go Fishing!” Florida Keys Saltwater Seminar and Fishing Tournament
Oct. 16 - 18 | Islamorada, Fla. Female fishing fans can learn or polish angling skills during the award-winning weekend seminar with two days of optional charter fishing and the Fishing Fever Fun Tournament. Learn more.
Cheeca Lodge & Spa All American Backcountry Tournament
Nov. 12 - 14 | Islamorada, Fla. Honor war heroes during Veterans Day weekend with this all-release tournament targeting snook, redfish, bonefish, tarpon, and permit. The event benefits the Bonefish & Tarpon Trust. Learn more.
Sugarloaf Showdown
Nov. 12 - 14 | Lower Keys, Fla. Fish for bonefish, permit, and barracuda in this catch-and-release challenge hosted by the Lower Keys Guides Association. Proceeds support the Florida Keys Guides Trust Foundation. Learn more.
Ready to plan your next trip? Get inspired at visitfloridakeys.com. Supporting high-resolution images and associated credit information are available HERE.
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Golf gets an island-style twist as a costumed participant takes aim at a floating green during the Conch Scramble Charity Golf Tournament in Islamorada in the Florida Keys. Foursomes trade golf carts for boats and traditional fairways for the water, teeing up biodegradable golf balls during the one-of-a-kind tournament, returning Sept. 25-26, 2026. (Courtesy of Conch Scramble)
Fantasy takes flight as Daniel Bitnar, center, leads a blue-winged group depicting the U.S. Navy's Blue Angels Flight Demonstration Squadron during a Fantasy Fest Masquerade March in Key West, Fla. The island city's anything-goes celebration of costuming, creativity and self-expression returns Oct. 16-25, 2026. (Andy Newman/Florida Keys News Bureau)
Things get wonderfully weird as colorful extraterrestrials and other out-of-this-world characters parade through Key West, Fla., during a Fantasy Fest Masquerade March. The island city's 10-day celebration of costuming, creativity and self-expression returns Oct. 16-25, 2026. (Carol Tedesco/Florida Keys News Bureau)
Only in Key West could the Kentucky Derby inspire a unicorn race. A group depicting an offbeat “Conch-tucky Derby” for unicorns performs on Duval Street during the Fantasy Fest Parade in Key West, Fla. The elaborate procession of fantastical floats and costumed marchers highlights the 10-day Fantasy Fest celebration, set for Oct. 16-25, 2026. (Andy Newman/Florida Keys News Bureau)
Duval Street gets a glow up after dark as participants in elaborate neon-accented costumes light up the Fantasy Fest Parade in Key West, Fla. Fantastical floats, marching groups and over-the-top characters fill the street during the signature procession of the 10-day celebration, set for Oct. 16-25, 2026. (Carol Tedesco/Florida Keys News Bureau)
Talk about a powerhouse pair. A costumed duo channels celebrity pals Martha Stewart and Snoop Dogg during the Fantasy Fest Pet Masquerade in Key West, Fla. Pets and their people share the spotlight in coordinated and themed costumes during the 10-day Fantasy Fest celebration, set for Oct. 16-25, 2026. (Carol Tedesco/Florida Keys News Bureau)
The undead hit the road as thousands of costumed cyclists take over the streets of Key West, Fla., for the annual Fantasy Fest Zombie Bike Ride. The wildly imaginative, family-friendly ride is among more than 60 events planned during the island city's 10-day Fantasy Fest celebration, set for Oct. 16-25, 2026. (Carol Tedesco/Florida Keys News Bureau)
The Tour de France meets the afterlife as Ryan Stachurski, left, and Tony Lopez pedal their Tour de France-inspired “Tour de Mort” creation during the Fantasy Fest Zombie Bike Ride in Key West, Fla. The quirky ride is among more than 60 events planned during the island city's 10-day Fantasy Fest celebration, set for Oct. 16-25, 2026. (Carol Tedesco/Florida Keys News Bureau)
Setting their sights on one of the Florida Keys' most recognizable landmarks, swimmers round the historic Alligator Reef Lighthouse during the 2025 Swim for Alligator Lighthouse off Islamorada. The eight-mile open-water challenge, which raises funds to help preserve the landmark, returns Sept. 12, 2026. (Christjen Johnson/Florida Keys News Bureau)
Kayak support teams are in it to win it as they guide swimmers past the historic Alligator Reef Lighthouse during the 2025 Swim for Alligator Lighthouse off Islamorada in the Florida Keys. The eight-mile open-water challenge combines endurance with a mission to celebrate and preserve the beloved offshore landmark and returns Sept. 12, 2026. (Steve Panariello/Florida Keys News Bureau)
A sure sign that fall has arrived in the Florida Keys: fresh Florida stone crab claws hit the table at Key Largo Fisheries. Stone crab season begins Oct. 15, bringing the sweet, locally harvested delicacy back to menus throughout the island chain. (Mary B. Haban/Florida Keys News Bureau)
Hollywood meets the subtropics as leading film critics gather to dish about movies and industry trends during the 2024 Key West Film Festival Critics Panel at Hank's Hair of the Dog Saloon in Key West, Fla. From left are moderator Shirrel Rhoades of The Key West Citizen, David Rooney of The Hollywood Reporter, David Fear of Rolling Stone, Stephanie Zacharek of Time and Lovia Gyarkye of The Hollywood Reporter. The five-day festival returns Nov. 18-22, 2026. (Larry Blackburn/Key West Film Festival)
Speed, spray and serious horsepower take over Key West Harbor as Stock 450-class raceboats make the turn during the 2023 Key West Offshore World Championship. The high-speed season finale, produced by Race World Offshore and featuring elite teams from around the world, roars back into Key West Nov. 1-8, 2026. (Andy Newman/Florida Keys News Bureau)
A prized permit provides a picture-perfect moment for an angler competing in the Sugarloaf Showdown in the Lower Keys. The catch-and-release challenge targeting bonefish, permit and barracuda returns Nov. 12-14, 2026, with proceeds supporting the Florida Keys Guides Trust Foundation. (Courtesy of Lower Keys Guides Association)
Hot from the oven, a wood-fired Neapolitan pizza draws smiles at Italian Food Company during a Taste the Keys trolley tour in Key Largo in the Florida Keys. The month-long culinary celebration is proudly presented by the Key Largo Chamber of Commerce and offers a variety of special menus and dining experiences throughout Key Largo and the Upper Keys Oct. 1-31, 2026. (Doug Finger/Florida Keys News Bureau)
Entrees like this herb-crusted shrimp at Sundowners restaurant are just some of the mouthwatering meals that have been offered during a Taste the Keys Foodie Trolley Tour in Key Largo. The month-long culinary celebration, presented by the Key Largo Chamber of Commerce, serves up a variety of special menus and dining experiences throughout Key Largo and the Upper Keys Oct. 1-31, 2026. (Doug Finger/Florida Keys News Bureau)
A 35.5-pound cobia earned Donna Jocelyn of Miami, Fla., left, Top Offshore honors during a previous Ladies, Let’s Go Fishing! event aboard Sea Horse with Capt. Rick Rodriguez. The Florida Keys Saltwater Seminar and Fishing Fever Inshore/Offshore Tournament returns Oct. 16-18, 2026, in Islamorada. (Photo courtesy of Ladies, Let’s Go Fishing)
Janet Steiner of St. Augustine, Fla., celebrates her first inshore fishing experience with a 33.5-inch snook release during a previous Ladies, Let’s Go Fishing! event. The catch earned her Top Inshore honors with Capt. Chris Hanson of Scales2Tales. The Florida Keys Saltwater Seminar and Fishing Fever Inshore/Offshore Tournament returns Oct. 16-18, 2026, in Islamorada. (Photo courtesy of Ladies, Let’s Go Fishing)
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 Florida Keys stretch over 125 miles, are 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, Public Relations
Visit Florida Keys & Key West
(305) 394-3142
Visit Florida Keys & Key West PR Agency (TURNER)