Key West Events

Annual Events

Address: West Martello Tower, Fort Zachary Taylor Historic State Park, Key West, FL Dates: January 10 - April 30, 2009 User rating:      (Rate It!)    |    Add to a Suitcase

This annual sculpture exhibit promises that, even in a tropical island paradise, contemporary art has its niche. Held every year since 1995, Sculpture Key West serves as an artistic statement and a source of pride for people who live and work on the island. The sculptures, which are done by internationally-known...

Address: 0 Duval St, Mallory Square, Key West, FL 33040 Dates: March 1 - December 31, 2009 User rating:      (Rate It!)    |    Add to a Suitcase

The sunset is, perhaps, Key West's most famous attraction, and this nightly celebration gives folks a great opportunity to see just how magical it can be. Jugglers, fire eaters, mimes and other buskers entertain the crowds as they wait for the "show" to begin. It's best to get there an hour or two early to "take it...

Address: 400 Front St, Hog's Breath Saloon, Key West, FL 33040 Category: Fair / Festival - Music Dates: April 29 - May 3, 2009 User rating:      (Rate It!)    |    Add to a Suitcase

With stages at the world-famous Hog's Breath Saloon, Sloppy Joe's Bar and other popular Key West watering holes, this festival is a sure-fire bet to draw big crowds and first-rate musicians each year. Past performers have included Wayd Battle, Christi Bauerlee and Dillon Dixon. Some events are free and some are...

Address: Various venues, Key West, FL Category: Fair / Festival - GLBT Dates: June 6, 2009 - June 2009 User rating:      (Rate It!)    |    Add to a Suitcase

One of Key West's most well-attended and most spirited events, PrideFest welcomes and embraces what organizers have dubbed "sea to sea diversity." Indeed, folks from all over the world and of all sexual identities converge on the Conch Republic every June, resulting in huge (often times colorful) turnouts for events...

Address: various locations, Key West, FL Category: Fair / Festival - Cultural Dates: July 21 - July 26, 2009 User rating:      (Rate It!)    |    Add to a Suitcase

Papa's seemingly everywhere when the annual Hemingway Days festivities roll around – and it's not because of posters and stage events all over Key West honoring the literary legend. No, the true culprit is the riotous Hemingway Look-Alike Contest held at Sloppy Joe's, the writer's favorite Duval Street watering hole....

Address: Duval and Petronia Sts, Bahama Village, Key West, FL Dates: October 17 - October 18, 2009 User rating:      (Rate It!)    |    Add to a Suitcase

Held in conjunction with the larger Fantasy Fest, this two-day party in Bahama Village is a fun-filled mix of terrific live music, food, drink and merrymaking that celebrates African and Island cultures. In addition to those activities, attendees will be able to shop vendors' stalls for clothing, beads, art, crafts...

Address: Duval St, Key West, FL Dates: October 23 - November 1, 2009 User rating:      (Rate It!)    |    Add to a Suitcase

This 10-day festival draws big crowds each year, providing a boon to local businesses during a time that, once upon a time, saw Key West almost devoid of tourist traffic. Highlighting the city's creative energies, Fantasy Fest features a full slate of themed parties – from clothing-optional partying at the Bull &...

Address: Southard St, Fort Zachary Taylor, Key West, FL Dates: November 28 - December 6, 2009 User rating:      (Rate It!)    |    Add to a Suitcase

If traditional sensibilities don't leave you thinking about swashbucklers, wooden legs, Jolly Rogers and hidden treasure between Thanksgiving and Christmas – Well, matey, it's obvious you need to spend the first week of December in the Conch Republic, living it up during the annual Pirates in Paradise Festival. Folks...

Address: Various Locations, Key West Dates: December 29 - March 13, 2010 User rating:      (Rate It!)    |    Add to a Suitcase

A true inside look at Key West, the home and garden tour is put on by the Old Island Restoration Foundation and gives visitors a chance to see how residents have restored and redecorated their historic residences. Tickets may be purchased a week prior to the tour you'd like to attend from Key West’s Oldest House & ...

Address: 0 Duval St, Ocean Key Resort & Spa’s Sunset Pier, Key West, FL Dates: March 6, 2010 - March 2010 User rating:      (Rate It!)    |    Add to a Suitcase

Lovingly known as the "Conch Honk," this waterside festival gives those who are full of hot air plenty of chances to toot their own ... um, shells. From kids to seniors, everybody wants to join in the fun, and the event always manages to draw huge crowds that are curious to see what all the hoopla is about. In...