An alphabetical list of the best bars and nightclubs, as well as a handful of notably gay-popular restaurants and cafés, in the famed Florida gay-resort mecca of Key West, located at the very southwestern tip of the scenic Florida Keys. With its many gay-owned inns and gay-friendly hotels, Key West has been a favorite destination among GLBT travelers for decades. Most of the gay bars in town are clustered along colorful Duval Street, in the historic district, which is also home to dozens of fun shops and inviting restaurants, some of them - because they're popular places to socialize - included here.
For tips on where to cruise and play around in town, check out the Key West Gay Bathhouses Guide.
Key West Gay Bar Guide - continued on Page 2
A snazzy, beautifully designed LGBT nightclub in the heart of the Duval Street bar and restaurant action, Aqua (711 Duval St., 305-294-0555) is run by the same management as one of the country's most successful women's clubs, Wallstreet, in Columbus, Ohio. This is the place to go when you're up for a full night of dancing and partying, and also to watch performances by the lovely and talented Aquanettes, arguably Key West's most iconic drag troupe. The elegant back-lit bar is a fun spot for daily happy hour, which kicks off at 5 pm each day. Aqua Idol Tuesdays, and karaoke on Saturday afternoons (as well as late Monday and Thursday) are popular times to be here, too.
Azur Key West - restaurant
A favorite spot in Old Town, near several popular gay resorts, the charming Azur Restaurant (425 Grinnell St., 305-292-2987) is a great choice for a romantic date, a casual but sophisticated lunch, a hearty breakfast (it's worth passing up your hotel's free pastries and coffee for this!), or cocktails in the evening. Chef Michael Mosi is wonderfully talented, preparing a number of creative specials each day (key-lime-stuffed French toast at breakfast, slow-braised beef with gnocchi at dinner), along with a menu of regular Mediterranean–meets–Key West dishes like charred marinated octopus salad with lemon zest and olio verde; fennel-roasted pork "Bay of Pigs" sandwich with salsa verde and Fontina; salt cod–and-potato croquettas; and grilled whole branzino (Mediterranean sea bass). Opt for a seat on the lovely patio, and do not miss dessert - lavender-infused crème brûlée is one of the stars.
Even by Key West's eccentric standards, Blue Heaven (729 Thomas St., 305-296-8666) is something of an offbeat place to eat. This rambling, colorfully painted house with a tree-shaded outdoor dining area that's routinely invaded by somewhat aggressive roosters opened in the early '90s and has been delighting fans with stellar soul, Southern, and Caribbean fare ever since - the breakfasts are especially tasty (try the pecan pancakes, or shrimp-and-grits - and be sure to ask for a side of Betty's banana bread). Lunch and dinner are served, too, with Jamaican Jerk chicken a favorite. The restaurant is just a block west of Duval Street, in the historic Bahama Village section of Key West.
Just a block off of busy Duval Street near the intersection with Truman Avenue, Bobby's Monkey Bar (900 Simonton St., 305-294-2655) is a bit less of a tourist haunt than some of taverns on Duval Street - think of it more as Key West's quintessential gay neighborhood bar, an enjoyable place to chat with friends, meet locals, shoot pool, and knock back extremely well-priced drinks. This is a very laid-back, festive place that's popular with men and women.
Open nightly until 4 am and consistently packed and notoriously cruise-y and fun, Bourbon Street Pub (724 Duval St, 305-294-9354) is an expansive layout of social spaces, with the ground floor occupied by a colorful and fun video bar, and the upstairs dominated by the men's clothing-optional resort, New Orleans House. Also part of the same group are 801 Bar and 1 Saloon, which are across the street, so there's quite a lot of opportunity to mingle and socialize at this stretch along Duval Street. Very popular at Bourbon Street is the lushly landscaped Garden Bar, a men's only spot where clothing is optional, and there's a nice big sundeck, a tiki bar, a pool, a hot tub, and plenty of room to kick back and enjoy yourself. Popular draws here include the stable of very attractive go-go dancers, the Saturday-afternoon pool parties around the Garden Bar, and the amateur strip contests held on Saturday nights.
This refined yet still informal restaurant in the historic Marquesa Hotel absolutely exudes romance and is a terrific choice for a special-occasion meal. Cafe Marquesa (600 Fleming St., 305-292-1244) is on the same street as several Key West gay resorts, which accounts in part for its strong LGBT following. But this is no hidden secret - foodies from all over flock here. Marquesa boasts one of the most extensive wine lists in the Florida Keys and serves deftly executed, creative modern American and European fare, with an emphasis on local ingredients. The menu changes often but has featured conch-and-blue-crab cakes with fennel slaw and remoulade; herb-crusted black grouper with sweet pea pesto; grilled spice-rub rib-eye steak with Jack Daniels mushroom sauce; and a "vegetarian feast" of couscous, Braised Fennel, caponata, oven-roasted tomatoes, and pear-and-cheese pasta purses. Cafe Marquesa is upscale, but prices are in line with plenty of lesser restaurants in town.
The cozy and inviting Coffee Plantation (713 Caroline St., 305-295-9808) occupies a charming little house not far from the Old Town port section of Key West. It's one of a handful of lovely little java places around town and one of the most popular with the gay community - although really everybody hangs out here. You can sip coffee on the small front porch or in one of the comfy armchairs inside, and there's also a section with computers for you to check your e-mail (there's Wi-Fi, too - free for an hour with any $6 purchase, or for $6 per hour).
A comfy, dependable spot for steaks, chops, and seafood, Duffy's Steak & Lobster House (1007 Simonton St. at Truman Ave., 305-296-4900) occupies a pale-green house just a block off of Duval. This is a popular spot with the gay community, and perfect is you're seeking straightforward, unfussy presentations of traditional American standards.
One of the standard bearers when it comes to Key West gay nightlife, 801 Bourbon Bar ((801 Duval St., 305-294-4737) has occupied the same coral-pink building for more than three decades. It's a favorite spot for drag cabaret - the "801 Girls" perform a couple of times per night. Other top events are bingo on Sunday afternoons, which is preceded by karaoke. In this laid-back gay pub, all-comers are welcome, and the crowd is pretty mixed in style and age. Adjacent to the bar is the sister hangout, 1 Saloon, which you can read more about elsewhere in this guide - it cultivates more of a leather/bear following.
For authentic Cuban cooking, it's worth venturing just a few blocks from Duval Street and the heart of Old Town to find El Siboney (900 Catherine St., 305-296-4184), an informal, noisy, and fun restaurant serving terrific Cuban fare and extremely fair prices. Inside the squat redbrick building you'll typically find a big crowd of Hispanic and Anglo diners convening over roast pork with black beans, Cuban sandwiches, ropa vieja, breaded steak, stuffed crab, barbecue chicken, conch chowder, and sweet plantains. It's hearty, honest, stick-to-your-ribs cuisine - the kind of cooking that'll fill you up and put a smile on your face. The family-owned restaurant is open daily for lunch and dinner.
For fans of Cuban sandwiches, a stop at 5 Brothers Grocery (930 Southard St., 305-296-5205, just block from historic Fleming Street and its several gay guesthouses) is de rigueur. The "Cuban Mix" sandwiches here are works of art - just flaky and fresh bread, lettuce, mustard, pickles, and mixed Cuban meats and cheese. There's also delicious (and potent) Cuban coffee, flans, barbecue pork, fried grouper sandwiches, and plenty of groceries, of course. Everything's fresh and tasty here.
This intimate, gay-owned bistro with a campy name is a fine option for dinner or drinks. Flaming Buoy Filet (424 Eaton St., 305-295-7970) may not take itself too seriously - it's definitely a fun vibe in here. But the food is seriously delicious and competently prepared, and there's a nice selection of wines (by the glass and bottle) and a handful of craft beers available. Food is classic "Floribbean" - a mix of tropical flavors, with an emphasis on seafood. The signature tuna-and-watermelon ceviche is a favorite starter, while great mains include the fresh catch of the day pan-seared with banana salsa, grilled corn-on-the-cob, and a broccoli cake with vegetables; and the "Filet Co. Three Way": an unusual chili (a variation on the famed Cincinnati chili) that combines dark chocolate and spices and is served over spaghetti with onions, sour cream, and cheddar. The filet mignon is superb here, too.
Grand Vin Wine Bar - mixed bar
(1107 Duval St., 305-296-1020) is a fun little place in a historic house on upper Duval Street, a perfect stop on your way home from the beach or before venturing out for a more substantial dinner elsewhere. It's a wine shop, and tastings are done regularly, but also a cute little bar where you can try any number of wines by the glass.
The infamously fun and sexy Island House (1129 Fleming St., 305-294-6284) has long been one of the country's most popular clothing-optional men's resorts. Since the current owners bought it and gave it a complete makeover quite a few years ago, it's remaining a top place to stay because of its 34 handsome, upscale rooms as well as the friendly and - depending where on the grounds you are, and when - sexually open vibe. Even if you don't stay here, this is a top destination in Key West for socializing and cruising, and day passes are available, which get you access to the gym, 24-hour steam room, poolside cafe and bar, Jacuzzi, and lovely grounds.
Along upper Duval Street you'll find this laid-back, upscale mixed gay-straight resort that has several extremely festive dining and drinking components. La Te Da Key West (1125 Duval St., 305-296-6706) houses the Cabaret in the famed Crystal Room, a top-notch theater that brings in exceptional talents from all over the world, from drag divas to Broadway singers to hilarious comics - regulars Randy Roberts and Christopher Peterson usually perform a few times per week. Then there's the fab By George Piano Bar, a lavishly decorated space in which local musicians entertain an always-colorful mix of locals and tourists. Another fun venue here is the open-air Terrace Bar, a relaxing, lantern-lighted garden area that's popular as the sun starts to drop and well into the evening. Plenty of patrons combine a visit to one or more of the bars with dining in the romantic Restaurant at La Te Da, which serves three meals daily - think sophisticated but quite reasonably priced American and Continental fare with Floridian touches, like sauteed Key West yellowtail snapper with brown butter and capers, and mango-barbecue pork chops.
For a few decades, Louie's Backyard (700 Waddell Ave., 305-294-1061) has been one of the great dining destinations of the Florida Keys - a refined, romantic, yet friendly restaurant that showcases the region's distinct Florida-meets-Caribbean fusion of contemporary cuisine. Louie's occupies a smartly restored Victoria house on a quiet street a few blocks from the southern end of Upper Duval Street. It's a hot spot for afternoon or sunset cocktails on the spacious Afterdeck Bar, which affords panoramic views of the ocean, and for informal eating and sipping in the Upperdeck/Wine Bar. For lunch or dinner, especially on weekends, it's not a bad idea to call for a reservation - this place is on plenty of foodies' short lists. Dishes like seared rare tuna cakes with orange-sweet chili sauce and wakame salad; Florida lobster braised in truffle butter and served with spinach and prosciutto; and grilled coriander-and-pepper-rubbed swordfish with cucumber, citrus, and Thai fried rice are testament to the kitchen's skill and dedication.
1 Saloon - gay bar
The bearish and brawny 1 Saloon (504 Petronia St., 305-294-4737) adjoins the 801 Bourbon Bar and is home base for Bone Island Bears - in fact, it's really the only gay leather hangout in town.