Published on December 30, 2025
In 2026, Florida Keys will be hosting their unique culture, adventures, and flavors, along with festivals & events. From food festivals to beachside music festivals and sports competitions, there is something for everyone!

Cultural Celebrations

The Florida Keys are famous for their rich cultural heritage and lively arts scene. In January, the Key West Literary Seminar brings together renowned authors and passionate readers for workshops and readings on the island that inspired literary legends like Ernest Hemingway. For those drawn to Celtic culture, the Florida Keys Celtic Festival in early January showcases traditional Irish and Scottish music, dancing, and food.

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Music lovers should not miss Mile 0 Fest from January 27-31. This five-day festival combines Texas Red Dirt music with Key West’s tropical charm. In February, the Presidential Families Weekend offers a chance to hear from the descendants of U.S. Presidents about their family’s legacies.
Throughout the year, the Keys host numerous other cultural events. The Key West Songwriters Festival in late April celebrates the art of songwriting with performances across more than 30 venues. In June, the Key West Pride Festival honors love and inclusivity with vibrant parades and parties. Hemingway Days in July pay tribute to the author with a range of activities, including look-alike contests and marlin fishing tournaments.

Food & Drink Festivals

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The Florida Keys are also known for their fantastic food, particularly seafood and tropical flavors. The Key West Food & Wine Festival kicks off the year, offering tastings, grand events, and island-inspired dishes. March brings the Marathon Seafood Festival, where visitors can enjoy fresh seafood, live entertainment, and family-friendly activities.
In July, indulge in the Key Lime Festival with its quirky pie contests, cocktail competitions, and the famous Pie Drop. If you’re in the mood for lobster, Key West Lobsterfest in August celebrates the Florida Spiny Lobster season with parties, live music, and lobster feasts.
Also in August, Rum Fest Key West offers rum tastings, Caribbean culture experiences, and optional Day Trips to Cuba. September’s Key West BrewFest celebrates craft beer with over 200 varieties available for tasting.

Adventure & Sports

The Florida Keys are a haven for adventure seekers and sports enthusiasts. One of the most picturesque races in the U.S., the Seven Mile Bridge Run, takes place in April. This 6.8-mile run over sparkling blue waters offers breathtaking views while supporting local youth athletics.
For diving enthusiasts, the Florida Keys Lionfish Derby in April invites participants to remove invasive lionfish from the Keys’ waters while supporting marine conservation. The KEYS100 Ultramarathon in May challenges athletes with a 100-mile race from Key Largo to Key West, with other options for shorter distances.
Water sports lovers will enjoy the Swim for Alligator Lighthouse in September, an open-water swim to support reef conservation. The Race World Offshore Key West World Championship in November features high-speed offshore powerboat races, attracting top teams and thrilling spectators.

Iconic and Quirky Events

No trip to the Florida Keys would be complete without experiencing some of its more unique events. The Conch Shell Blowing Contest in March invites participants of all ages to make music with the iconic conch shell. The Conch Republic Independence Celebration in April celebrates the playful spirit of Key West with parades, battles, and quirky events.
The Underwater Music Festival at Looe Key Reef in June is a whimsical concert for snorkelers, complete with coral-friendly messaging and sea creature costumes. The Fantasy Fest in October is one of the Keys’ most famous events—a 10-day costume extravaganza full of themed parties, parades, and extravagant outfits.
Lastly, New Year’s Eve Red Shoe Drop in Key West offers a quirky twist on the traditional ball drop, featuring a local drag queen descending in a giant red high heel, signaling the start of the new year.

World-Class Fishing Tournaments

Fishing is a major draw in the Florida Keys, and 2026 will feature several notable tournaments. In late January, the Ladies, Let’s Go Fishing! Islamorada Women’s Sailfish Tournament offers beginners a chance to learn and compete in this exciting sport. The Marathon Premiere Sailfish Tournament in April and the Marathon Offshore Bull and Cow Dolphin Tournament in May promise high-stakes competition and exciting prizes.
In the fall, the Take Stock in Children Backcountry Challenge in September is a fishing contest that supports scholarships, and the Sugarloaf Showdown in November offers anglers a chance to compete for prizes while targeting species like bonefish and permit.

A Guide for Travelers

The Florida Keys are a world-class destination with unique culture, food, and adventure with signature events throughout the Keys. Participate in a fishing tournament, music by the water, or try the seafood at one of the many festivals – the Keys have it all! Because the festivals have many attendees, make sure to buy your tickets and book your accommodations early.
Check the Florida Keys government tourism site for the latest travel tips, events, and accommodation info. You can legally visit the Florida Keys any time of the year but note that some events are popular and need early registration. Make sure to enjoy the many adventures that await in the Florida Keys.

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Tags: events 2026, Florida Keys, Islamorada, Key West, Key West festivals

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