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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.

More food festivals in Key West

Key West Lobsterfest ★ 4.4

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.

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.

Key West Brewfest ★ 4.1

Key West Brewfest pours more than 50 breweries at the Southernmost Beach Resort each autumn, a Sunrise Rotary fundraiser for its scholarship fund.

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.

Bahama Village Goombay Festival ★ 4.5

The Goombay Festival fills Petronia Street with Bahamian food stalls, junkanoo drums and dancing each October, Key West's opening act for Fantasy Fest.

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.

Key West Food & Wine Festival ★ 4.5

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.

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.

Florida Keys Seafood Festival ★ 4.6

The Florida Keys Seafood Festival piles Truman Waterfront Park with grilled spiny lobster, stone crab and conch every February, run by the fishermen themselves.

Tip: The $10 gate fee funds the Commercial Fishermen's Association; the operator lists the next edition as February 13 to 14, 2027.

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