February 25-26, 2012. 2-day juried outdoor fine art festival, over 100 artists. Watercolors, oil & acrylic, sculpture, & photography - along Whitehead Street from Greene to Eaton, & on Caroline Street through the Presidential Gates to Truman Annex.
June 6-10, 2012. A festival of several days of events around town, dance parties, drag shows, bike tours, water excursions, a street fair, and culminating with the parade on Duval Sreet.
July 18-22, 2012 (also November 29 - December 4, 2012), hundreds of gay naturists & guys who like to get naked, let it all hang out. Dance parties, foam parties, pool parties, even naked shopping. Check website for more info & schedules.
Each August. Key West's hottest event for men: four days of all-male adult-oriented theme parties, entertainment, and men from around the globe. See their website for schedule and more information.
Each September. Events typically include pool party, and Leather Party, in previous years held at the Saloon One. Check their website for this year's line-up of events.
October each year. Week-long series of events brings visitors to the island in the off-season. The event kicks off each year with the Coronation Ball, where they crown a king and queen. The party ends with a parade of 70,000 costumed revelers.
One of Key West's arguably lesser-known aspects is the island's large Cuban-born population. Cuban revolutionary Jose Marti, for example, fired up supporters from the balcony of what is now La Te Da on Duval Street. You can sample great Cuban food in several places in Old Town.
The Key West Cemetery, located at the base of Solares Hill in Old Town, is one of the best places to appreciate the island's rich and varied history. Look for the grave of Edwina Lariz, who described herself as a "devoted fan of singer Julio Iglesias" on her tombstone.
Captain Steve and his crew on the Blu Q catamaranoffer a variety of clothing-optional snorkeling, kayaking and sunset cruises that bring passengers to coral reefs, sand bars and other areas roughly 10 miles west of Key West. You're almost guaranteed to see sea turtles, barracuda, sharks and other denizens of the deep.
The best way to explore Old Town is on bike. The city has installed numerous bike lanes to accommodate bicyclists. With its highest point at only 18 feet above sea level, even novices will have little difficulty navigating Key West's streets.
