Make your Valentine feel as special as he or she is! Make memories in Key West by starting aboard the Key West Express. Visitors are drawn to the southern charm and Caribbean influences of this laid-back island city, only 4 miles long by 1.5 miles wide. During the day or at night, the island is alive with sidewalk cafes, world-class restaurants, fishing, watersports, shopping, performing arts, musical entertainment and galleries before the island gathers each evening at Mallory Square for the world renown sunset celebration.
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Five days. Five continents. A collection of chefs, winemakers, artists and unforgettable Key West settings.
The Key West Food & Wine Festival returns January 27–31, 2027, with intimate dinners, wine experiences, tastings and special events held at locations across the island. Now celebrating its 18th edition, the festival turns Key West into a culinary journey where the setting is just as memorable as what is poured and served.
The 2027 theme, “Connected by the Oceans,” explores how water has carried ingredients, cooking traditions, wine culture and human stories between continents. It is an especially fitting idea for Key West, an island shaped by the Atlantic Ocean, the Gulf and generations of cultural exchange.
If you are thinking about attending, this guide covers the dates, theme, announced events, venues, ticket information and practical tips for planning a delicious winter getaway.
