The people of Key West celebrate their rich history and culture through an array of lively fairs and festivals throughout the year, some of which are uniquely local. On such festivals you can book a Key West condo or a Key West vacation rental and see look-alikes of Hemmingway, Jimmy Buffet "parrotheads", pirates, motorcycle aficionados, Bahamian Junkanoo performers, world class sailors and fishermen or scarcely clad Fantasy Fest revelers.
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Pirates in Paradise fair
The fair is held from November 30 to December 03. Historic Key West and Fort Taylor are transformed into pirates’ dens with over 150 pirate entertainers. You can witness tall ships, sea battles, arts and crafts, pirate sails, a living history encampment and nonstop entertainment celebrating Key West maritime history.
The Annual Florida Keys Seafood Festival
Held in the month of January, the festival is a foodie’s delight. During the festival the vendors, nonprofit organizations and commercial fishermen present fresh local seafood that includes lobster, fish, stone crab claws, conch chowder, conch fritters, conch salad and much more.
Annual Key West Island Kwanzaa
The Bahama Conch Community Land Trust presents Annual Key West Island Kwanzaa from 26 December to First January to honor the African ancestors of the Diaspora. The celebrations are held with ceremonies, rituals and feasts. The festival aims at promoting the communication and interaction between the diverse African communities settled in Key West and surrounding areas.
Florida Keys Medieval Festival
The festival brings alive the spirit of the bygone era of knights and nobles and includes chess matches and jousts. A feast featuring King Henry VIII is held to resurrect the sixteenth century atmosphere. The festival is held for the benefit the Big Brothers and Big Sisters of Monroe County.
