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 […]
12 events found.
Events
Featured
Sloppy Joe’s Annual Hemingway Days
Sloppy Joe's 201 Duval Street, Key West, FL, United StatesHemingway 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 […]
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, […]
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 […]
October 15 – 23, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse opens its season with an encore presentation of Hedwig and the Angry Inch, staged as […]
Featured
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, […]
November 12 – 14, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse launches its Spotlight Series with the Florida premiere of , a solo play written by […]
Sunday, November 22, 2026 Key West Theater, 512 Eaton Street The Buena Vista Orchestra comes to the Key West Theater, billed by its presenter as the world's foremost Cuban music […]
