Overview Taste of Key West is a sunset food and wine evening at Truman Waterfront Park, where Key West restaurants from Alonzo's Oyster Bar to Yessi's Ceviche Bar serve tastings by the dollar ticket, and the money goes to the island's health and housing nonprofit. The nonprofit is AH Monroe, founded in 1986 in HIV care, whose work runs to testing, prevention, LGBTQIA+ health services and housing across the Florida Keys; the 2027 Taste carries its new name, Keys Health + Housing. It counted its 2025 Taste as 30 years, and the 2026 edition was the 31st. On site The evening runs 6 to 9 p.m. on the waterfront. Entry is free: guests buy tasting tickets at a dollar each, most dishes take four to six, and a glass or plate is bought separately. A Two for Taste pass bundles 60 tickets and two commemorative glasses. The VIP tent adds unlimited food and wine, butler-passed hors d'oeuvres, a sommelier, lounge seating and its own tables. In 2026 more than 50 restaurants, chefs and beverage partners took part, among them Four Flamingos, Hot Tin Roof, Square Grouper, Sunset Pier, Green Parrot and Matt's Stock Island Kitchen and Bar, and sommeliers poured alongside the wine, beer and spirits. Audience The nonprofit pitches the night to friends, neighbors and local businesses, and the 2026 restaurant list was the island's own, from the dining rooms at La Concha and Oceans Edge to food trucks, a ceviche bar and a church ice cream truck. General admission guests pay as they go, ticket by ticket. Track record The 2026 Taste was one of two events for AH Monroe's 40th anniversary, paired with a seated Vintners Dinner at Williams Hall two nights earlier. RNDC donated the beer and wine for 2026. The nonprofit's own case stories name what the money reaches: Marty's Place, where a resident rebuilt his life in an affordable apartment, and the Lofts at Bahama Village, where a lifelong neighborhood resident and her son moved into their first stable home. Brand presence In the 2026 anniversary year a single Platinum partner took the presenting name on both the Taste and the Vintners Dinner, with its own sponsor booth on the waterfront. Emerald partners got on-site activation space, Diamond partners shared a sponsor showcase area, and one of them could host the VIP tent, with a sponsor table and staff inside it. Every level from Diamond up came with a VIP table for ten, and the 2026 sponsor wall ran Emerald through Bronze plus community sponsors.