Top Choice Cultural in Key West

Fantasy Fest

Akin to New Orleans' riotous Mardi Gras revelry, Fantasy Fest is 10 days of burlesque parties, parades, street fairs, concerts and loads of costumed events. Bars and inns get competitive about decorating their prope…
Food & Drink in Marathon

Marathon Seafood Festival

One of the biggest fests in the Keys is this food-loving event that takes over Marathon one weekend in March. You'll find live music, an art and boat show, an arts and craft market, and ample amusement for the kids …
LGBT in Key West


One of North America's biggest lesbian celebrations, Womenfest is four days of merrymaking, with pool parties, art shows, roller derby, drag brunches, sunset sails, flag football, and a tattoo and moustache bicycle …
Literature in Key West

Key West Literary Seminar

A feast for the literary minded, this four-day yearly event draws top novelists, poets and historians from around the country (although it costs hundreds of dollars to attend). Most book signings and presentations t…
Cultural in Key West

Goombay Festival

Held during the same out-of-control week as Fantasy Fest, this is a Bahamian celebration of food, crafts and culture. The family-friendly event runs over two days (typically a Friday and Saturday).
Cultural in Key West

Hemingway Days Festival

This long-running fest brings parties, a 5km run, a fishing tournament, arm-wrestling contests, a 'Papa' look-alike contest and the running of the bulls (with mock animals pulled on wheels).
Cultural in Key West

Conch Republic Independence Celebration

A 10-day tribute to Conch Independence; vie for (made-up) public offices and watch a drag queens' footrace.
Music in Key West

Meeting of the Minds

This festival is for, you guessed it, Jimmy Buffett fans (rabid ones only, naturally).
Literature in Key West

Robert Frost Poetry Festival

Named for Robert Frost, who wintered on Key West from 1945 to 1960, this festival hosts readings, lectures and workshops.