DEL BROWN 2026 TOURNAMENT July 12 - 15, 2026 Celebrate a Fly Fishing Legend: Del Brown The Del Brown Permit Tournament is an exclusive and prestigious fly fishing tournament. This annual […]
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Outdoor Activities
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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 […]
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, […]
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 […]
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 […]
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 […]
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. […]
