The Florida Keys & Key West is a big draw for travelers seeking culture, cuisine and quirky island traditions. From marquee Pride celebrations and literary tributes to culinary festivals and conservation-driven adventures, the destination’s 2026 lineup delivers fresh reasons for repeat visits and new client itineraries alike.
The Key West Food & Wine Festival (Jan. 28–Feb. 1) brings Pacific Coast flavors to tropical settings, followed by Presidential Families Weekend over Presidents Day, where descendants of U.S. presidents share personal stories at the historic Truman Little White House.
Spring heats up with Island Fest in Islamorada, the iconic Conch Shell Blowing Contest, and the tongue-in-cheek Conch Republic Independence Celebration, a multi-day event blending parody, parades and maritime traditions.
Summer brings some of the Keys’ most recognizable celebrations, including Key West Pride in June, Hemingway Days in July—complete with look-alike contests and a local take on the “Running of the Bulls”—and the zesty, crowd-pleasing Key Lime Festival, which culminates with the famous pie drop from the Key West Lighthouse.
Adventure travelers can also tap into conservation-focused events such as Coralpalooza and the Florida Keys Lionfish Derby, both combining hands-on marine education with immersive island experiences.
Fall is anchored by culinary and cultural heavy-hitters, including Taste the Keys, a month-long Upper Keys dining celebration, REEF Fest in Key Largo for divers and snorkelers, and the wildly creative Fantasy Fest, Key West’s legendary 10-day costume extravaganza. Film buffs can cap off the season at the Key West Film Festival, featuring screenings at historic theaters and outdoor island venues.
Rounding out the year, anglers can plan trips around high-profile fishing tournaments in Marathon and Key West, while the destination’s signature flair shines during the New Year’s Eve Red Shoe Drop, a uniquely tropical take on ringing in the new year.
For a full list of events in the Florida Keys & Key West, visit visitfloridakeys.com.
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