Hemingway 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 of the 20th century, Ernest Hemingway. Held annually in sunny Key West, this event celebrates Hemingway’s life in Key West and enduring legacy in a […]
Celebrating its 45th year, the 2026 Key West Marlin Tournament, featuring $50,000 in cash prizes in the Marlin Division and more in the Fun Fish Division, is set for July 22 -25, 2026. The tournament, coinciding with the annual Hemingway Days Celebration in Key West, Florida, is a world-class fishing event drawing anglers eager to test the […]
Get Ready to Crack! Key West Lobsterfest 2026 Dates are Set! The wait is officially over! Get your butter warmers ready because we are thrilled to announce the dates for the biggest and tastiest summer celebration on the island: Key West Lobsterfest 2026 is happening from Wednesday, August 5th through Sunday, August 9th! Join us for five unforgettable […]
Key West Rum Fest 2026 — August 10–16 The Florida Keys' Key West Rum Fest returns August 10–16, 2026, with a week of global rum tastings, live music, culinary events, and island excursions. Proceeds benefit MARC Inc., a Keys-based nonprofit serving adults with developmental disabilities. Set against the backdrop of Key West's tropical island culture, […]
Tropical Heat is the HOTTEST annual 5-day party for gay men ages 21 and up in Key West and the Florida Keys! The all-male themed parties, pool parties, clothing optional events, and adult-oriented entertainment promise to be HOT! August on our tropical island is always HOT, but during Tropical Heat it promises to be even […]
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 The Key West Business Guild proudly presents the 43rd Anniversary Edition of the Headdress Ball — one of the most anticipated events of the Fantasy Fest Celebration, on Thursday, October 22, 2026, at the Coffee Butler Amphitheater at Truman Waterfront Park. Doors open at 6:30 PM, with the show beginning at 8:00 PM. This unforgettable […]
National Series Event Key West World Championship November 1st - 8th, 2026 ADRENALINE & HIGH SPEED Experience Step into the exhilarating world of Race World Offshore, where the ocean becomes a high-speed battleground for cutting-edge boats and fearless competitors. Welcome to Race World Offshore, where every moment is a celebration of nautical prowess and […]
Thank you for joining the festivities for our 29th Anniversary! Weekend of January 15-17, 2027 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 destination. […]
2027 Key West Food and Wine Festival 1/27/26 - 1/31/27 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 their regions. This journey spans five continents with […]
