Local Annual Events

This renowned championship is hailed as the “richest sailfish tournament in the world,” boasting more than $1,000,000 in prize money. The World Sailfish Championship raises funds for charity and provides guests with five adventure-filled days of gourmet cuisine, entertainment and, of course, high-stakes action.

The Conch Republic is less a place and more a state of mind. With the motto, “We seceded where others failed,” the Republic celebrates its “independence” from Key West each year with parties, concerts and good-natured, tongue-in-cheek fun.

Support a good cause while wining and dining on local cuisine, courtesy of over 50 restaurants and 100 wineries and vineyards. The Taste of Key West event raises funds for the organization, AIDS Help. Admission is free, and food and wine tastings start at just $3.

The globe’s grandest songwriters’ gathering, the Key West Songwriters Festival has been celebrating the art of songwriting since 1997, with a five-day-and-night party that thrills writers, musicians and crowds with fantastic music and even better company.

Key West Pride started with a march down Duval Street about 30 years ago, with gay and straight men and women sharing our community’s message of acceptance and inclusion. Today, Pride, with a motto of “One Human Family,” celebrates the same simple message on a grander scale, with themed parties, events, activities and a whole lot of fabulous fun.

Celebrate the Fourth of July in Key West with a spectacular fireworks show at White Street Pier, perfectly visible from the Casa Marina. Enjoy the festivities from our exclusive Cabanas and Daybeds, providing premium seating for an unforgettable Independence Day experience.  RESERVE >

Literary stalwarts unite for fun and fandom at Hemingway Days, a festival dedicated to the renowned writer and punctuated by readings, book signings, an awards ceremony for a literary competition, and even a Hemingway lookalike contest. For the still more adventurous, a marlin tournament, a “Running of the Bulls,” and a paddleboard race promise to get hearts pounding.

Lobster lovers hightail it to Key West for the annual Lobsterfest, a four-day-and-night long celebration of everyone’s favorite crustacean. Partake in some of our favorite festivities: a lobster boil, a bar crawl that benefits a local scholarship fund, a street fair, concert and the indulgent lobster brunch.

Start off the legendary Fantasy Fest with a bang at the Bahama Village Goombay Festival. This heart-pounding street party features costumed dancers, lively music, an array of African crafts, and delicacies from the world over. Don’t forget to swing by the main stage for around-the-clock Caribbean music and entertainment.

Hailed as the infamous “party in paradise,” Fantasy Fest is a raucous festival for adults looking to get a little wild, Key West style, on their next vacation. Ten days packed with parades, cocktails, cosplay and costumes add up to one unforgettable Fest.

The Key West Film Festival is an annual celebration of contemporary cinema in a historically rich, artistically vibrant, and culturally diverse island community.

Hailed as the world’s “biggest and fastest” offshore racing series, Super Boat International draws crowds to Truman Waterfront each year. The action-packed racing schedule and impressive watercraft fleet inspire racers and audience members alike.

Pirate invasions, plank walking championships, bone-chilling reenactments: The Pirates in Paradise Festival has it all. Kids and kids at heart can catch a thrill at this multi-day affair designed to invoke the swashbuckling spirit of the Keys.