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 […]
