The Orchid Bar at the Orchid Key Inn serves up creative elixirs alongside the lush pool garden, including martinis infused with local ingredients ( 1004 Duval Street, 30). Or take home a printed porcelain tile from KW Light Gallery ( 1203 Duval Street, 30). ( 605 Simonton Street, 30) or Cuba! Cuba!, where colorful original paintings line the walls ( 814 Duval Street, 30). Cigar making is also a big deal here-visit the area known as Cigar Alley and the multitude of shops along Duval selling fat hand-rolled stogies. Sure it’s touristy, but you’ll find local merchants selling everything from island fashions to gourmet coffee and candy.
Skip the tacky t-shirt shops and head for the Clinton Square Market ( 291 Front Street, 30).
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Looking for some schooling on local gay history? The Key West Gay & Lesbian Museum and Archive tells the story of Southern LGBT life-including that of Richard Heyman, one of the country’s first openly gay mayors ( 513 Truman Avenue, 30). Ernest Hemingway is considered a native son, and his home (with its famous six-toed cats) is still one of the most popular attractions-for good reason ( 907 Whitehead Street, 30). The bars and restaurants along Duval are the ultimate places to see and be seen. New York has its big shiny ball, but every New Year’s Eve a drag queen named Sushi is lowered from atop the Bourbon Street Pub in a big red stiletto ( 724 Duval Street, 30).
Not only does Key West have its share of eye candy year round (think white-washed architecture and handsome beach bums), but the sparkling vista has been influenced by everything from rich Cuban culture (it’s just 90 miles away) to the literary lore of Ernest Hemingway and Tennessee Williams, who penned some of their most famous works in this artsy coastal community. This almost six-square-mile island has become a destination of choice for gay snowbirds. (or whenever your liver quits).Photos courtesy of the Key West Gay & Lesbian Convention & Visitors Bureau You’ll find naked go-go boys to spare, or toss caution (and your swim trunks) to the wind and hang out at the clothing-optional New Orleans House upstairs. Pub (724 Duval St.), but leave whatever’s left of your inhibitions at the door. The best place to end your night is the popular video bar Bourbon St. If you’re there for one of Aqua’s nightly drag performances by the Aquanettes, you’ll still get a chance to get in the spotlight, as the folks seated in the dance floor area tend to get accosted - we mean “incorporated” - into the show. If you’re feeling inspired, head down to Aqua (711 Duval St.) for some karaoke Monday through Thursday starting at 11 p.m. (If you prefer your company more rough and tough rather than plucked and tucked, Key West’s leather and Levi’s bar, 1 Saloon, is also right next door.) and 11 p.m., and you can make reservations for the show online. You’ve got a few places to catch a drag show in Key West, but 801 Bourbon Bar (801 Duval St.) boasts the 801 Girls, including the legendary queen Sushi. Once you’ve knocked back a few cold ones, it’s time to sit back and be entertained. The crowd at Bobby’s is mixed gay and straight, but when you’re shooting pool (or the breeze) in such a relaxed environment, no one seems to mind. Belly up to the bar and chat up a bartender or one of the friendly local regulars that frequent the beloved dive. For those who like their bars small and smoky, Bobby’s Monkey Bar (900 Simonton St.) is a must-see.