30th Annual Fantasy Fest
October 17-26, 2008
10-day celebration featuring costume competitions, promenades, street fairs and a grand parade with floats.

Key West World Championship
November 2-9, 2008
High-speed powerboats continue Key West’s longstanding tradition in a challenge described as the Indianapolis 500 of powerboat racing.

Pirates in Paradise 2008
November 29-December 07, 2008
Daily Tall Ship Pirate Sails & Sea Battles - Pirate Pub Strolls - Fight Circles - Sea Stories

Key West New Year’s Eve Celebrations
December 31, 2008
A celebration with a conch shell drop at Sloppy Joe’s Bar, 201 Duval St.

27th Annual Key West Literary Seminar
January 8-18, 2009
“HISTORICAL FICTION and The Search for Truth.” Two sessions, One Workshop, Many speakers.

Fort Lauderdale - Key West Race
January 14 - 16, 2009
A 160-nautical-mile sprint down the Florida Keys.

Acura Key West 2009
January 19-23, 2009
International sailing regatta.

Conch Republic Independence Celebration
April 17-26, 2009
“We Seceded Where Others Failed”

14th Annual Taste of Key West
April 20, 2009  6-9pm
More than 50 local restaurants and 100 wineries and vineyards, provided by Republic National Distributing Company, will be on hand to provide culinary delights and fine wine tastes.