What’s Unfolding in the Florida Keys Fall of 2026

by Noreen Kompanik
Last updated: 7:00 AM ET, Fri September 11, 2026

Fall in the Florida Keys offers warm days, balmy breezes, island vibes and a calendar packed with festivals, flavors and fun.

A new initiative from Visit Florida Keys & Key West offers deals and savings across the island spotlighting a variety of lodging, restaurants, watersports operators and attractions. Two local eateries, Blue Heaven and Moondog Café & Bakery in Key West both earned Michelin Guide recognition. Stone crab season kicks off October 15, anglers can take advantage of world-class fishing and milder temperatures are ideal for snorkeling, boating and biking.

Florida Keys and Key West fall events and experiences include:

Swim for Alligator Lighthouse, 9/12, Islamorada: One of the Florida Keys' most iconic athletic challenges features an eight-mile swim drawing participants from around the world for the challenging journey.
Conch Scramble Charity Golf Tournament 9/25-9/26, Islamorada: The unique, experience brings the island bravado with floating greens, foursomes traveling by boat, biodegradable golf balls, creative costumes, decorated boats, food, festivities and awards.
Lower Keys Fall Migration Mania Birding & Nature Adventure 9/27, Key West: At the Key West Tropical Forest & Botanical Garden, birders, butterfly enthusiasts, and nature lovers can explore this premier wildlife habitat during the fall migration peak.
Taste the Keys, 10/1-31, Upper Keys / Key Largo: The culinary celebration showcases the restaurants, chefs and creativity of Key Largo and the Upper Keys. Participating restaurants offer specially prix-fixed menus inspired by local ingredients and island culture.
Celebrate Sunset on the Old Seven Mile Bridge 10/10, Marathon: This uniquely Florida Keys event brings residents and visitors together for an evening of local food, live music, history, culture, and community spirit.
SOMO Half Marathon & 10K, 10/11, Key West: Experience the Conch Republic with a scenic race route along the waterfront with breathtaking island views and a festive atmosphere.
REEF Fest, 10/15 - 18 | Key Largo: 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 renowned destination for reef exploration.
Fantasy Fest 10/16 - 25 | Key West: The world-famous 10-day extravaganza features more than 60 events, including themed parties, masquerade balls, art walks, street fairs, the spectacular Fantasy Fest Parade along Duval Street, Zombie Bike Ride and Pet Masquerade to the Royal Coronation Ball and Goombay Festival.
Trop Rock'N Duval, 10/28 – 11/1 Key West: Five days of live performances with over 60 artists performing across 23 Key West venues.
Race World Offshore Key West World Championship 11/1- 8 Key West: 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.
9/11 Exhibit, Army Knights and Drone Shows, 11/18 & 20, Islamorada & Big Pine Key: Includes Experience the Tunnel to Towers “Never Forget” traveling 9/11 exhibit, a U.S. Army Knights paratrooper drop-in and spectacular drone show 11/18 at Founders Park in Islamorada and patriotic programming at Big Pine Key Community Park on 11/20 followed by a 5K run.
Key West Film Festival, 11/18 – 22, Key West: Named one of MovieMaker Magazine's “25 Coolest Film Festivals in the World,” the festival brings cinematic excellence to paradise in a five-day event.
Tour de Keys, 11/21, Key Largo/Islamorada/Marathon/Lower Keys/Key West: Charity ride from either Key Largo (100 miles) or Marathon (50 miles) to Key West benefitting MARC organization that supports adults with developmental disabilities.

Fall Fishing events include:

Herman Lucerne Memorial Backcountry Fishing Championship, 11/18 – 20, Islamorada: Honoring “Mr. Everglades,” the tournament challenges anglers to catch seven specific species within Everglades National Park waters.
Take Stock in Children Backcountry Challenge, 11/25 – 27, Key Largo: Catch-and-release tournament in support of local vocational programs and scholarships for Upper Keys youth.
IGFA Permit Invitational, 9/29 – 10/2, Lower Keys: Premier tournament celebrating world-class inshore game fish, fly fishing, the ethics and the programs of the International Game Fish Association.
Backcountry Fly Championship Series, 10/2 – 3, Islamorada: Compete to catch the most inches of snook and redfish in a challenge where one-inch equals one point.
Casting for Cats Backcountry Tournament, 10/16 – 17, Islamorada: The formerly all-female tournament is now open to everyone, with a co-ed division and a new junior division as a major fundraiser to help control the Upper Keys feral cat population.
“Ladies, Let’s Go Fishing!” Florida Keys Saltwater Seminar and Fishing Tournament, 10/16-18, Islamorada: 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.
Cheeca Lodge & Spa All American Backcountry Tournament, 11/12 – 14, Islamorada: Honor war heroes during Veterans Day weekend with this all-release tournament benefitting the Bonefish & Tarpon Trust.
Sugarloaf Showdown, 11/12 -14 Lower Keys: A catch-and-release challenge hosted by the Lower Keys Guides Association to support the Florida Keys Guides Trust Foundation.