JanuaryLate January, 5 daysTicket needed
The Key West Food & Wine Festival fills five late-January days with ticketed tastings, seafood strolls and chef dinners at venues right across the island.
Focus: Wine and island dining
Tip: Each event sells its own ticket and the strolls sell out early; the operator lists the next edition as January 27 to 31, 2027.
FebruaryMid-February weekendTicket needed
The Florida Keys Seafood Festival piles Truman Waterfront Park with grilled spiny lobster, stone crab and conch every February, run by the fishermen themselves.
Focus: Local seafood
Tip: The $10 gate fee funds the Commercial Fishermen's Association; the operator lists the next edition as February 13 to 14, 2027.
JulyJuly 4th week, 5 days
The Key Lime Festival takes over Key West across the July 4th week with a pie-eating championship, a pie hop and a sip-and-stroll, running since 2012.
Focus: Key lime pie
Tip: The Pie Eating Championship and the Sip & Stroll book out first; the operator has already posted the next edition as July 1 to 5, 2027.
AugustWednesday to Sunday in August, 5 days
Key West Lobsterfest greets spiny lobster season each August with a lobster boil, pub crawl and a Saturday street fair running the length of lower Duval.
Focus: Florida spiny lobster
Tip: The free Saturday street fair fills the 100-500 blocks of Duval and the ticketed lobster boil sells out. The 29th edition runs 11 to 15 August 2027.
OctoberLate September to early October weekendTicket needed
Key West Brewfest pours more than 50 breweries at the Southernmost Beach Resort each autumn, a Sunrise Rotary fundraiser for its scholarship fund.
Focus: Craft beer
Tip: The organisers list the 2026 festival week as September 30 to October 4, with the grand tasting itself on October 3 at the Southernmost Beach Resort.
OctoberThe Friday and Saturday that open Fantasy Fest, mid-October
The Goombay Festival fills Petronia Street with Bahamian food stalls, junkanoo drums and dancing each October, Key West's opening act for Fantasy Fest.
Focus: Bahamian and Caribbean street food
Tip: Vendors run noon to midnight on both days and entry is free. Goombay opens Fantasy Fest, so its October weekend moves with the parent festival.