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 festival hosted by the Key West Sunrise Rotary of the Conch Republic and the Southernmost Beach Resort. It's a fully nonprofit event, with proceeds going […]
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 […]
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, […]
46th Annual Key West Marlin Tournament July 21–24, 2027 · Key West Celebrating 46 years of world-class sportfishing, the Key West Marlin Tournament returns to Key West July 21–24, 2027. The tournament coincides with Hemingway Days, drawing anglers eager to test "The Wall" — the deep blue water off Key West — while the island […]
2027 Dates: 8/11 - 8/15 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 […]
Mark your calendars! We are already looking ahead and can’t wait to do it all over again. Please join us for the 29th Annual Key West Lobsterfest, taking place August 11–15, 2027. ______________________________________________________________________ Get Ready to Crack! Key West Lobsterfest 2026 Dates are Set! The wait is officially over! Get your butter warmers ready because we are […]
