Florida Keys & Key West Announce Signature Events for 2026

America’s most southernmost island, the Florida Keys, has released its lineup of festivals, flavors and island fun slated for 2026.

The yearly roundup includes sunny days, tropical breezes and unique offerings to include:

Culture, Music and Island Vibes

• Key West Literary Seminar (January 8-11). Features stories by the sea bringing 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. 
• Florida Keys Celtic Festival (January 10-11). A family-friendly celebration of Celtic music and culture featuring Celtic rock and traditional Irish and Scottish music, dancing, food and highland athletics.
• Mile 0 Fest (January 27-31). Texas Red Dirt meets turquoise water in a five-day blend of Americana music, beachfront stages, live music sails and sunsets.
• Presidential Families Weekend (February 14-16). Descendants of U.S. presidents share stories about their relatives’ service as Presidents of the United States.
• Gigantic Nautical Market (February 21-22). An outdoor market, boat show and food truck rally takes place throughout Founders Park in Islamorada.   
• Island Fest (March 28-29). Islamorada’s annual juried art fest with live music, food, classic cars and live entertainment.   
• Key West Songwriters Festival (April 29-May 3). The world’s biggest songwriter festival spreads across 30+ venues, giving fans a front-row seat to the stories behind the songs.  
• Key West Pride (June 3-7). Celebrate love, joy, and Key West’s famous “One Human Family” spirit with drag shows, pool parties, comedy nights, and the dazzling Pride Parade.
• Hemingway Days (July 22-26). With Hemingway look-alike contests, a ‘Running of the Bulls’ (Key West version), marlin fishing, and birthday bashes, the event honors the legendary author’s bold, mischievous spirit with five days of fun.   
• Womenfest (September 2-6). One of the world’s premier LGBTQ+ celebrations brings sun, sea, themed parties, and empowering connections to the welcoming island.
• REEF Fest (October 15-18). Divers, snorkelers and ocean lovers unite in Key Largo to celebrate their love of marine life and learn about the latest in conservation.
• Key West Film Festival (November 11-15). With screenings at historic theaters and breezy outdoor venues, the festival showcases standout films, documentaries, shorts, and Florida talent. 

Food & Drink Events: A Taste of the Tropics 

• Key West Food & Wine Festival (January 28-Feb 1). Celebrates food and wines from the Pacific Coast in tropical Key West settings, including the Grand Tasting at Audubon House and Tropical Gardens.
• Marathon Seafood Festival (March 14-15). Fresh seafood, live entertainment and family fun at Marathon Community Park.
• Key Lime Festival (July 1-5). Key West’s zestiest celebration with pie tastings, cocktail competitions, the famous Pie Drop from the lighthouse, and the Key Lime Pie Eating Championship.
• Key West Lobsterfest (August 5-9). Opens 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.
• Rum Fest Key West (August 12-16). A sip, savor, and celebrate Caribbean culture event with premium rum tastings, a Rum Cake Competition, Ti Punch Brunch, and optional Day Trips to Cuba.
• Key West BrewFest (September 5-7). Over Labor Day Weekend, enjoy more than 225 craft beers at beachside tastings, pool parties, and flavorful pairing events.
• Taste the Keys (October 1-31). The month-long culinary celebration of the Upper Keys returns with prix-fixe menus, Foodie Trolley Tours, chef showdowns, and beachfront dinners. 

 

Florida Keys Lighthouse Swim (Photo Credit: Andy Newman/Florida Keys News Bureau)

Adventure & Sports in Paradise 

• Seven Mile Bridge Run (April 11). One of the most scenic races in the world, a 6.8-mile journey over brilliant blue water, supports local youth athletics.
• Florida Keys Lionfish Derby (April 23-26). Hosted by Reef Environmental Education Foundation (REEF), this hands-on conservation event invites divers and snorkelers to help remove invasive lionfish from Keys' waters.
• KEYS100 Ultramarathon (May 16-17). Includes 100 miles from Key Largo to Key West (plus 50-mile and 50K options), finishing steps from the sand at Higgs Beach.
• Key Largo Triathlon (August 16). Sanctioned by USA Triathlon, the event takes place at John Pennekamp Coral Reef State Park and surrounding areas in Key Largo.
• Swim for Alligator Lighthouse (September 10-12). Swimmers take on an eight-mile open-water challenge to an offshore lighthouse and back to support reef conservation.
• Race World Offshore Key West World Championship (November 6-13). High-speed, heart-thumping offshore powerboat racing electrifies Key West with the sport’s biggest teams and boldest maneuvers.
• First State Bank Key Largo Bridge Run (Dates TBD). 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 Gateway to the Keys."   
• Key West Triathlon (Dates TBD). Mixes competition with vacation, offering multiple race distances along Key West’s sparkling shoreline. 

Iconic, Quirky & Totally Unique: Only in the Keys 

• Conch Shell Blowing Contest (March 7). A Key West tradition for more than 60 years, the “Conch Honk” sees contestants of all ages trying to create their best sounds with the iconic conch shell.
• Conch Republic Independence Celebration (April 17-26). 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.
• Coralpalooza (June 7). Divers from across the globe join the Coral Restoration Foundation for reef restoration dives during this ocean conservation event.
• Underwater Music Festival (Dates TBD). Grab fins and a snorkel for a whimsical underwater concert at Looe Key Reef, complete with “sea creature” costumes and coral-friendly messaging.
• Fantasy Fest (October 16-25). Key West’s legendary 10-day costume extravaganza with themed parties, Tutu Tuesday, Zombie Bike Ride, and a spectacular parade.   
• New Year’s Eve Red Shoe Drop (December 31). Ring in the new year Key West–style as a local drag queen descends from the sky in a giant red high heel, a tropical twist on the Times Square ball drop. 

World-Class Fishing Tournaments 

• Ladies, Let’s Go Fishing! Islamorada Women’s Sailfish Tournament (January 30 – February 1). Perfect for beginners, this weekend blends hands-on learning, friendly competition, and the unbeatable thrill of fishing in the Florida Keys.
• Marathon Premiere Sailfish Tournament (April 17-18). A competitive fishing tournament and a non-profit supporting fishing and recreational opportunities for disadvantaged children.
• Marathon Offshore Bull and Cow Dolphin Tournament (May 1-3). This competitive tournament pays a guaranteed $20,000 for the largest bull and cow dolphin combined weight, or $30,000 with 100 or more boats entered.
• Key West Marlin Tournament (Dates TBD). Teams compete for $50,000 in prizes chasing marlin, spearfish, and fun-fish species.
• Take Stock in Children Backcountry Challenge (September 25-27). 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.
• Sugarloaf Showdown (November 12-14). Anglers vie for awards in multiple divisions, including fly, spin and youth targeting bonefish, permit and barracuda.

 

Topics From This Article to Explore

DestinationsFloridaNorth AmericaUnited StatesTravel Intel