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 - 6th, 2026 Five Days of Celebration in Paradise! Get ready to turn up the volume and celebrate bold, brilliant, and iconic women through the […]
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 to changes and errors and omissions.) Full schedule & tickets on sale May 1 April 28 for package holders April 30 for badge holders WEDNESDAY, […]
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 of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. […]
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 Headdress Ball, one of the most anticipated nights of Fantasy Fest. Legendary Key West entertainer Randy Roberts returns as host, with music by WEOW's RudeGirl. […]
45th Annual Key West Offshore World Championship November 1–8, 2026 · Truman Waterfront Park, Key West The 45th Annual XINSURANCE Key West World Championship runs Sunday, November 1 through Sunday, November 8, 2026, at Truman Waterfront Park. It's the season finale of the Race World Offshore calendar and the oldest continuously run event on the […]
29th Annual Key West Half Marathon & Runfest® January 13–18, 2027 · Race weekend January 15–17 Key West offers a multitude of exciting experiences, from its diverse restaurants and vibrant nightlife to the numerous museums and art galleries. The wide range of water sports options adds an extra layer of adventure, making it an unforgettable […]
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 festival of 2025 by USA Today, Mile 0 Fest turns Key West into a five-day music vacation each January. Evening shows run at the Coffee […]
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 & Wine Festival 2027 A curated journey through the culinary heritage of five continents, featuring world-renowned chefs, their signature dishes, and the legendary wines that define […]
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 Key West. For just $10 admission, enjoy two full days of fresh, local seafood, live music, activities, and the vibrant island atmosphere that make this festival a […]
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 over the Truman Waterfront for one evening each spring. Sample your way through dishes from dozens of the island's best restaurants, work through curated wines, […]
The Key West Songwriters Festival. 4/28/27 - 5/2/27 The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy […]
Key Lime Festival July 1–5, 2027 · Key West America's Favorite Citrus Celebration In the Florida Keys we celebrate the things that make our islands unique: citrus, eccentrics, people, and pie. The Key Lime Festival is five days of exactly that — pie tastings, cocktail strolls, wild competitions, and a whole island leaning into its […]
