In Key West, located 159 miles southwest of Miami by road, temps have never dropped to freezing since the National Weather Service began keeping records in 1872. The island’s lowest temperature ever recorded is 41 degrees, reached in January 1886 and again in January 1981.
Winter temperatures sometimes dip into the low 60s, inspiring local residents to pile on layers of clothing. Summer temps can rise to the upper 80s, but breezes from the nearby Gulf Stream make the 2-by-4-mile American Caribbean island cooler than most mainland Florida destinations.
With sunshine nearly 365 days a year, sunset is celebrated each night with a lively street carnival at Mallory Square.
The island’s near-perfect climate means the calendar is so packed with events and celebrations — many designed to appeal specifically to LGBTQ visitors — that any time is a good time to arrive.
October, for example, brings Key West’s most popular event, the 10-day Fantasy Fest (fantasyfest.com), a rollicking celebration of costuming and masking events reminiscent of Mardi Gras in New Orleans or Carnival in Rio de Janeiro. During the outrageous Fantasy Fest extravaganza, attendees are invited to discard their inhibitions and slip into a realm of masked fantasy.
Drag abounds, as do elaborate and plentifully plumed costumes. The event is capped by a parade showcasing world-class floats, costumes and revelry that must be experienced to be believed. The campaign for king and queen of the festivities traditionally raises well over $100,000 each year for the Florida Keys’ A.H. of Monroe County, formerly called AIDS Help.
The Key West Business Guild’s Headdress Ball (headdressballkeywest.com) is a highlight of Fantasy Fest, astounding spectators and participants with jaw-dropping handcrafted headpieces that can exceed 10 feet in height.
New Year’s Eve draws large-scale crowds to applaud the annual “Red Shoe Drop” (bourbonstpub.com/newyearseve.html) starring drag diva Sushi. Dazzlingly gowned and perched in a supersized red high-heel shoe hanging above Duval Street, Sushi presides over the festivities at the Bourbon St. Pub/New Orleans House complex. After performances by female impersonators and other entertainers, Sushi and the shoe “drop” from the complex’s balcony to mark the new year’s arrival.
Other annual celebrations may be less flashy, but are equally appealing. Each spring drama fans can celebrate the life and work of Tennessee Williams, award-winning playwright of “The Glass Menagerie” and “A Streetcar Named Desire” among others, on the island he called home for more than three decades. Dennis Beaver, founder of the Tennessee Williams Key West Exhibit, also established the Tennessee Williams Birthday Celebration (twkw.org).
April’s Conch Republic Independence Celebration (conchrepublic.com) commemorates the anniversary of Key West’s symbolic 1982 secession from the Union, protesting a U.S. Border Patrol checkpoint. Among its highest-profile events is an annual “drag race” featuring high-heeled, big-haired racers competing for bragging rights and prizes.
In June, the five-day Key West Pride (keywestpride.org) salutes the island’s diversity and renowned One Human Family philosophy with featured events including a Pride parade along Duval Street. Contests, tea dances, on-the-water excursions, pool parties, a street fair and late-night gatherings abound.
August’s steamy temperatures bring Tropical Heat (tropicalheatkw.com), an adventurous long weekend of all-male adult fun. The roster includes happenings that range from pool parties to drag shows to late-night gatherings at island clubs.
In September, the five-day Womenfest Key West (womenfest.com) attracts thousands of women for high-energy revelry and camaraderie. The event traditionally offers poolside and late-night parties, musical and comedy performances and on-the-water excursions. Key West’s accepting atmosphere makes it the ideal setting for singles, couples and groups of women to enjoy themselves.
In addition, while Britain revered its Queen Mother and honors its current queen, Key West boasts a queen for every season. The island’s pageants and contests range from the Miss Firecracker Contest to a Queen Mother Pageant.
Florida Keys calendar of events: fla-keys.com/calendarofevents
Key West visitor information: fla-keys.com/gay, fla-keys.com/keywest or 1-800-LAST-KEY
Gay Key West Visitor Center: gaykeywestfl.com, 305-294-4603 or 1-800-535-7797
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