Key West: With or without clothing?

My first visit to Key West was during high school, on a decidedly non-gay trip with my Uncle Ed and Aunt Agnes. As we strolled along the main commercial strip known as Duval Street, my uncle suddenly called out, “I think that’s a gay bar!” This year, I can finally say that I’ve visited this feisty little Florida city as an adult — and yes, the bar that attracted my uncle’s attention is, indeed, gay.

Actually, a rather large percentage of Key West’s businesses are gay. You’ll meet a mish-mash of LGBT travellers from around the United States in Key West, as well as quite a few from Canada and across the ocean. You also may see a fairly large number of these visitors naked, thanks to the clothing-optional gay hotels and bars.

Key West’s decidedly progressive attitude about gay life is just one aspect of its overall uniqueness. Closer to Cuba than Miami, Key West was once an exceedingly wealthy port city — and briefly a secessionist US breakaway known as the Conch Republic (in the 1980s, believe it or not). Today, this heat-soaked island is likely one of the most liberal gay hotspots in the United States.

To get a feel for Key West’s gay essence, my partner and I checked into Island House, a men-only, clothing-optional hotel that’s been a gay guesthouse since 1976. The property’s current owners have spent an estimated $2.5 million on renovations over the past decade, and the results are quite attractive. The hotel is a social hub on its own, and it’s also a good base for chatting up locals and visitors alike to get the scoop on the city’s best activities. During the day, we rented bicycles and explored the city, which is graced with beautiful historic architecture as well as stunning water views.

Key West’s gay nightlife is centred mostly on Duval Street, a bustling thoroughfare lined with shops, restaurants and bars. Bourbon St Pub is the largest of the gay venues, with handsome go-go boys and an outdoor bar in the back complete with swimming pool and a clothing-optional Saturday afternoon party. Weekly events include drag shows at 801 Bourbon, and a good resource for learning about the latest events is Q Magazine, which features information about nightlife, events, tours and other activities — including gay snorkel and sunset cruises with a local tour company called Blu Q.

Shedding the pretenses
“That guy is going to bottom for me tonight,” proclaimed a young, drunk employee from the Equator Resort who was hanging out at the men-only, clothing-optional outdoor bar at Bourbon one Friday night. He pointed at a 20-something blond standing at the bar wearing nothing but his underwear.

When I jokingly volunteered to be the official photographer to document his hookup, the Equator employee turned his attention to my boyfriend and me, asking us how long we’d been dating. “If you’ve been together that long, I hope you’re in an open relationship,” he said after hearing our response. “Because otherwise it seems pretty boring to me!”

Within a few minutes, he was making an attempt to lower my boyfriend’s pants to check out his goods, both front and back, and did the same to his own friend, who was standing nearby. Getting naked — and encouraging others to do so — is nothing out of the ordinary in Key West. In addition to clothing-optional hotels like Island House, bars are rather laissez-faire places. Two weekends every year, the city hosts an event called Bone Island Bare It All (Key West was originally called Cayo Hueso, which means Bone Key in Spanish), with activities including dance nights, foam and pool parties and even naked shopping. Fantasy Fest, the annual bacchanal that takes place in October, is another must-see gathering of revellers.

Since Key West’s natural beauty and laid-back environment attracts a variety of travellers, it’s only natural that sometimes worlds collide. One night, we saw a wide-eyed group of preteen girls frozen in place in front of Bourbon, gawking at a ravishing, dark-haired go-go boy on the bar inside who was wearing assless briefs and knee-high athletic socks.

“Shield your eyes,” joked a guy sitting in the window next to us.

“Don’t worry,” said the woman with the girls. “They’ve seen lots more than that. I’m their foster mother.”

On another night, I saw a towering drag queen crouched outside of 801, chatting with an awestruck little girl. “You’re so pretty!” she told the child. “Can you say hi?” The girl’s mother beamed and asked if she could take a photo of her daughter with the drag queen.

This city’s relaxed vibe attracts plenty of new residents as well. One afternoon, we had lunch at Sarabeth’s, one of the city’s award-winning restaurants, where the 50-something waitress explained what convinced her to move to Key West many years ago. “I came here for love and a boat,” she said.

For the most up-to-date travel information on gay Key West, see our City Guide, Listings Guide, Events Guide and Activities Guide.