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Key West Holiday Fest | December

Key West Holiday Fest features a series of enchanting holiday-themed events this November. It kicks-off with the Lighting of the Harbor Walk of Lights at the Historic Key West Bight on Wednesday, November 25th at 6:00 pm. Gather at Green and Elizabeth Streets for the best viewing, and visit Seaport restaurants and shops. The Harbor Walk of Lights stretches the entire length from Green Street to the Ferry Terminal. In December, tour festive decorated inns during this year's annual Holiday Historic Inn Tour and taste fine wine and light appetizers. The Annual Lighted Boat Parade is Key West's magical nautical display of lights and creativity, and takes place on December 5th at the Historic Seaport. Key West Holiday Fest's full schedule, available at, includes these events and others including holiday jazz concerts, snorkeling trips, pet photos with Santas and much more.

Key West World Championship Race | November

High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West's longstanding tradition in this 31st annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power. For more information visit or call (305) 296-6616 

Fantasy Fest | October

Fantasy Fest is an annual, adult-themed, 10-day party in paradise. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe leave their children and inhibitions behind as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement! Each year, Fantasy Fest adopts a theme to help inspire fun costuming and amazing parade floats. This year's theme is Animeted Dreams & Adventures. For the uninitiated, Anime is a traditionally Japanese form of animation with diverse art styles. Over the past two decades, Anime has exploded onto the Western scene and sparked a costuming lifestyle known as cosplay. So get those costumes ready because this October, East meets Key West in what is sure to be an unforgettable Fantasy Fest! For more information visit

Womenfest | September

For over twenty-five years Key West has welcomed women from across the globe to Key West Womenfest, the southernmost party for lesbians and their friends. Womenfest offers a wide range of activities guaranteed to appeal to a broad range of interests on a tropical island that is close to perfect but far from normal! Make plans to join us this year! For more information visit 

Key West Brewfest | August

More than 150 beers and micro-brews are on to be tap at this "tasty" annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the great activities on tap. For more information visit or call 800-354-4455. 

Hemingway Days | July

The 33rd annual celebration of the legendary author's work and lifestyle features literary readings, a theatrical premiere, short story competition, fishing tournament, Sloppy Joe's Look-Alike Contest and a pre-birthday "party" commemorating Ernest's July 21st birthday. 

Key West Pride | June

Street Fair, Pride Parade, Pool Parties, Dance Parties, Sunset Sails, Comedy, Film and so much more! All set on a tropical island that is legendary for its laid back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or get lost in the magic of our tropical island, rediscover Key West and discover how one island’s One Human Family philosophy has created one of the most integrated and unique communities in the world! For more information visit

Key West Songwriters Festival | May

The 20th-annual showcase of musical magic features America's foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. Visit for more information.

Annual Conch Republic Independence Celebration | April

With activities ranging from wacky bed race to a lighthearted sea battle featuring tall ships, the Conch Republic's 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys. For more information visit or call (305) 296-0213. 

Old Island Art Days | February

The Old Island Days Art Festival is a two day juried outdoor fine art festival. This nationally recognized show brings over 100 fine artists to this beautiful historic area of Key West. Exhibitors will set up along Whitehead Street from Greene Street to Eaton, and on Caroline Street through the famous Presidential Gates into the beautiful Truman Annex. Set among historical attractions such as Audubon House, the Little White House and Mel Fisher Museum, the City of Key West closes two blocks of Whitehead Street and another block of Caroline Street to vehicle traffic for the show. For more information go to or call Lois Songer at (305) 294-1243. 

Key West Food & Wine Festival | January

The fifth annual Key West Food & Wine Festival will be January 27- February 1, 2015. The Festival is set to turn up the heat in Key West. Events range from extravagant walk-around tastings during our famous sunset, to educational wine and food seminars led by our local talent, to local funky events you would only expect to experience in Key West. We are celebrating the culinary arts in this community which boasts such a rich food and drink heritage. For more information visit or call (800) 474-4319.