This almost six-square-mile island has become a destination of choice for gay snowbirds. 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.
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, 305-294-9354). Yes, Key West is that gay. The bars and restaurants along Duval are the ultimate places to see and be seen. 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, 305-294-1136). 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, 305-292-3223).
Skip the tacky t-shirt shops and head for the Clinton Square Market (291 Front Street, 305-296-6825). Sure it’s touristy, but you’ll find local merchants selling everything from island fashions to gourmet coffee and candy. 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. Pick up some art from Haitian Art Co. (605 Simonton Street, 305-296-8932) or Cuba! Cuba!, where colorful original paintings line the walls (814 Duval Street, 305-295-9442). Or take home a printed porcelain tile from KW Light Gallery (1203 Duval Street, 305-294-0566).
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, 305-296-9915). If craft beer is more your taste, The Porch specializes in a sophisticated selection of suds (429 Caroline Street, 305-517-6358). Or have a gay old time at 801 Bourbon Bar, where drag queens perform nightly (801 Duval Street, 305-294-4737), or at lesbian-friendly Aqua (711 Duval Street, 305-294-0555). The hotel La Te Da has three levels of entertainment, including a cabaret, restaurant and open-air terrace (1125 Duval Street, 305-296-6706).
The gay male resort scene is very popular here, making it tough for women to find a lesbian-friendly alternative. But Alexander’s Guesthouse is both gay- and lesbian-friendly, with whitewashed rooms and a beautiful pool and spa area (1118 Fleming Street, 800-654-9919). Pearl’s Key West also caters to women (525 United Street, 305-292-1450), while The Island Guest House is just for men who like to show off their finest, um, assets—it’s been voted among the best (clothing optional) gay male resorts in the country (1129 Fleming Street, 800-890-6284). Prefer something more low-key? Cypress House is a historic B&B in Old Town—within walking distance of all the action—that offers a sophisticated experience on a former estate dating back to the late 1800s (601 Caroline Street, 305-294-6969).