Finding a place to have a drink in Key West is not a problem. Deciding which of the endless number of bars is right for you may be a bit harder. With the exception of a few places with very specific audiences, most every pub and club in Key West is personable and without pretense; even when a cruise ship is docked and Duval Street seems flooded with sunburned tourists, it still seems as if most of the barstools are taken up with yarn-spinning locals. Bars in Key West open very early and close very late.
Worth noting: there are a handful of adult-oriented businesses that prey on drunk men who are looking for sexual favors. Without getting into a debate over whether these places are exploitative or whom they’re exploiting, let it be said that several of these businesses in Key West have less-than-stellar reputations for a wide range of reasons. Do yourself a huge favor and avoid them; there are plenty of other opportunities for legal adult pleasures in Key West.
The clothing-optional Garden of Eden (224 Duval St., 305/296-4565, 10 a.m.–4 a.m. Mon.–Sat., noon–4 a.m. Sun.) is upstairs from the somewhat more traditional open-air environment of the Bull & Whistle. The Garden of Eden’s prohibitions against cameras and insistence on patrons’ usage of towels on the deck chairs keeps the goings-on as decent as one could expect at a bar staffed by topless bartenders and populated with a mixture of the nude, the partially nude, and the blushingly curious. Frozen drinks seem to be the preferred libation.
The 801 Bourbon Bar & Cabaret (801 Duval St., 305/296-1992, 10 a.m.–4 a.m. Mon.–Sat., noon–4 a.m. Sun.) is a multibuilding entertainment complex for gay men. The Bourbon Street Pub is a massive bar that’s all about drink specials, drag shows, and dancing; upstairs is the all-male New Orleans Guest House. Across the street at the corner of Duval and Petronia Streets is the 801 Bourbon Bar, with its downstairs bar and upstairs cabaret shows, and a handcuffs-and-paddles leather bar known as the One Saloon.
Key West is legendarily gay-friendly, and in addition to 801, nightclubs like Aqua (711 Duval St., 305/294-0555), bars like Bobby’s Monkey Bar (900 Simonton St., 305/294-2655) and Kwest (705 Duval St., 305/292-8500) and even hotel complexes like La Te Da (1125 Duval St., 305/296-6706) and Pearl’s Rainbow (525 United St.) all strive to provide comfortable, fun, and safe environments. Gay men and women are unlikely to find much static in any of the bars and clubs along Duval Street, whether or not they’re focused on a specifically gay clientele.
There are a few bars in Key West that are tourist magnets; Hog’s Breath Saloon (400 Front St., 305/296-4222, 10 a.m.–4 a.m. Mon.–Sat., 10 a.m.–midnight Sun.) and Sloppy Joe’s (201 Duval St., 305/294-5717, 9 a.m.–4 a.m. Mon.–Sat., 9 a.m.–midnight Sun.) are on almost every day-tripper’s drinking itinerary and are best avoided when a cruise ship is in port. At night it’s not so bad, but still not great; Sloppy Joe’s is the better of the two, not because of its 80-year history and Hemingway affiliations but because of its quiet and largely vacant backroom bar, where you can enjoy a midday beer or cocktail without lining up behind scores of tourists.
The open-air bar at Willie T’s (525 Duval St., 305/294-7674, 10 a.m.–4 a.m. Mon.–Sat., noon–4 a.m. Sun.) is a far better option for visitors strolling the tourist strip looking for a beer while still being able to watch the parade of humanity traipse by on Duval Street. The atmosphere here is personable and a little ramshackle, but they serve great mojitos and even have a decent food menu.
Alternately, one can head for the Smallest Bar In Key West (124 Duval St., 305/509-2904, 10 a.m.–4 a.m. Mon.–Sat., noon–4 a.m. Sun.), which is frequently packed and loud…though that isn’t difficult to achieve, considering the place is about 6 feet wide by about 15 feet deep.
Locals tend to gravitate toward places like the Green Parrot Bar (601 Whitehead St., 305/294-6133, 10 a.m.–4 a.m. Mon.–Sat., noon–4 a.m. Sun.) that are friendly, unpretentious, and somewhat off the beaten tourist track. Open since 1890, the bar is simple and fun with a great blues-filled jukebox and occasional live music.
Somewhat more upscale is the Grand Vin Wine Bar & Store (1107 Duval St., 305/296-1020), a cozy, comfortable wine bar with a small but decent selection of bottles available for sale. Tastings are available, and you can have your bottle opened for a relaxing drink on the gorgeous front porch.
© Jason Ferguson from Moon Florida, 1st Edition