Unlike other leading LGBT resort destinations, Key West is a place where the good times know no season and the year-round climate is as warm as the welcome you’ll receive. In fact, Key West is the only frost-free city in the continental United States — featuring an average annual temperature of 77.7 degrees and sunshine nearly 365 days a year.

Key West beach

The locals’ favorite beach, located at Fort Zachary Taylor Historic State Park (sometimes called Fort Elizabeth Taylor) beckons year-round in Key West. (Photo by Rob O’Neal, Florida Keys News Bureau)

Winter days might see a brief drop in the mercury (to perhaps a low of 65 degrees) and late-summer afternoons might reach a sultry 88 degrees or so. But in general, the nearby Gulf Stream and the ever-present tropical breeze make the island’s climate pretty close to perfect. Even during the current summer days, onshore sea breezes tend to make Key West and the Florida Keys the coolest area in the state.

On top of the favorable year-round climate, the year-round calendar is so packed with events and celebrations (many that appeal specifically to LGBT visitors) that any time is a good time to escape to Key West.

For example, in late October each year, virtually the entire island sheds its everyday persona and slips into the realm of fantasy — Fantasy Fest, that is. Attendees at this internationally renowned 10-day masking and costuming extravaganza are invited to abandon “real-world” constraints and indulge in exuberant revelry.

Drag abounds, as do elaborate and kitschy costumes of all kinds. The event is capped with an outrageous parade whose world-class floats, costumes and pageantry must be experienced to be believed. And the campaigns for king and queen of the festivities traditionally raise more than $100,000 annually for the Florida Keys’ AIDS Help organization.

The Key West Business Guild's Headdress Ball is an exuberant evening where entrants show off their over-the-top headgear. (Photo courtesy of the Key West Business Guild)

The Key West Business Guild’s Headdress Ball is an exuberant evening where entrants show off their over-the-top headgear. (Photo courtesy of the Key West Business Guild)

The Key West Business Guild’s Headdress Ball is one of the festival’s most elaborate spectacles. Visitors come from all over the world to show off their exotic decorated headpieces, which can exceed a stunning 10 feet in height.

Other annual celebrations may be less flashy, but they’re equally appealing. Womenfest, for example, takes place in early September each year, attracting several thousand women to the island for a schedule that typically includes cocktail galas, music and comedy performances, films, sun-drenched beach bashes and on-the-water highjinks. Key West’s romantic, open-minded atmosphere makes it the ideal setting for both ladylike and unladylike fun.

April brings the Conch Republic Independence Celebration, marking the anniversary of Key West’s 1982 secession from the Union protesting a U.S. Border Patrol checkpoint. Among the commemoration’s highest-profile events is an annual “drag race” featuring high-heeled, big-haired racers competing for bragging rights and prizes.

Each June, the island population celebrates Key West Pride, presented by the Key West Business Guild. Festivities include a spirited parade, street fair, performances and parties. The event often involves a tribute at the Key West AIDS Memorial, the first such municipally sponsored memorial in the United States.

Key West rainbow flag

The late Gregg McGrady (left) and Mark Ebenhoch display an iconic section of Key West’s sea-to-sea rainbow flag.

In 2003, Pride hosted the unfurling of a 1.25-mile-long “sea to sea” rainbow flag constructed by Gilbert Baker, creator of the original rainbow flag, to celebrate the 25th anniversary of the iconic banner’s birth. More than 2,000 gay and straight people gathered to carry the flag from the Gulf of Mexico to the Atlantic Ocean along the island city’s famed Duval Street.

Each August brings Tropical Heat, a long weekend of adult fun. Conceived by the Key West Business Guild, the event showcases local bars and clubs as well as the island’s warm weather and enthusiastic welcome.

In addition, while Britain revered its Queen Mother and honors its current queen, Key West boasts a queen for every season. The island’s drag pageants and contests range from the southernmost Queen Mother Pageant to a Miss Firecracker Contest — and it’s not unusual to see a roomful of tiara-bedecked queens companionably exchanging royal gossip at local charity events.

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