2026 Dates - JUNE 3rd - 7th CELEBRATE ONE HUMAN FAMILY The Key West Pride event is one of the largest and most popular LGBTQ celebrations in the United States. Full […]
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Festivals
Events
JUNE 8-21, 2026 Join us for our 2026 summer solstice celebration For two weeks, the Sunset Celebration transforms into a vibrant Solstice Festival filled with live entertainment, local art, interactive experiences, island-inspired […]
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Sloppy Joe’s Annual Hemingway Days
Sloppy Joe's 201 Duval Street, Key West, FL, United StatesHemingway Days 7/21/26 - 7/26/26 Key West’s Most Whimsical Tribute to Papa Hemingway Welcome to the Key West’s most iconic and whimsical tribute to one of the greatest literary figures […]
Experience the ultimate girls' weekend at Key West Womenfest Key West Womenfest is an annual end-of-summer festival celebrating lesbians and attracting thousands of women from around the globe. September 2 […]
2026 JAFF SCHEDULE Preliminary schedule — subject to change All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject […]
October 1 – 5, 2026 · Grand Tasting: Saturday, October 3, 3–8pm Southernmost Beach Resort, 1319 Duval Street, and venues across the island Key West oktoBREWfest is an island-wide beer […]
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Key West Fantasy Fest!
October 16 - 25, 2026 2026 Theme: Musical Icons & Iconic Musicals Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group […]
Key West Headdress Ball Thursday, October 22, 2026 · Coffee Butler Amphitheater at Truman Waterfront Park Doors 6:30pm · Show 8:00pm The Key West Business Guild presents the 43rd Anniversary […]
Mile 0 Fest Key West January 26–30, 2027 · Truman Waterfront Amphitheater and venues across the island 10th Anniversary — Red Dirt, Americana & Texas Country Named the #1 music […]
2027 Key West Food and Wine Festival January 27–31, 2027 5 continents ~ 5 wines ~ 5 stories ~ 5 dishes ~ 5 chefs Welcome to Key West Food & […]
Florida Keys Seafood Festival FEBRUARY 13-14, 2027 Two Days of Seafood, Music & Family Fun! Join us for the 20th Annual Florida Keys Seafood Festival at Truman Waterfront Park in […]
Taste of Key West Monday, April 5, 2027 · 6:00–9:00 PM · Truman Waterfront Park Key West's Premier Food & Wine Festival Key West's biggest food and wine night takes […]
