Located literally at the end of the road, Key West has welcomed gay travelers for decades.
The island, known to locals as the Conch Republic, is roughly 90 miles north of Cuba and 160 miles south of Miami. This geographic isolation from mainland Florida and its anti-gay politics remains one of the island's best assets. The island's police chief is gay. And the city's other elected officials are either gay or gay-friendly.
Although thousands of cruise ship passengers crowd the narrow cobblestone streets around Mallory Square on a daily basis, the island has maintained its anything-goes reputation. Key West's tropical climate affords visitors the perfect opportunity to shed their clothes and sunbathe nude. It is not out of the realm of possibility to see men in thongs or g-strings and topless women on the main drag of Duval Street.
Key West is certainly not a destination for either the prudish or those seeking an action-packed vacation. This island's residents go out of their way to ensure visitors experience their slower pace of life with an added touch of hedonistic-fueled fun.
Located two miles east of downtown, Key West International Airport offers a variety of daily flights to Atlanta, Fort Lauderdale, Miami and a handful of other southern cities. A taxi from the airport to Duval Street should cost under $10. The Blue and Green Routes operated by Key West Transit (305-809-3910) shuttle between the airport and locations around the city.
Many Key West visitors opt to fly into Miami International AIrport, which is roughly 150 miles to the north. They pick up rental cars and drive south via the Overseas Highway. The Keys Shuttle (305-289-9997) makes daily trips between the airports at Fort Lauderdale and Miami to destinations throughout the Keys. Greyhound (800-231-2222) also offers two daily trips between Miami and Key West.
A rental car is not necessary once you arrive in Key West. Key West Transit operates buses across the island and the Lower Keys, but bicycles and mopeds are among the more popular ways to get around. Moped Hospital offers daily and weekly rentals. Old Town Trolly Tours is a hop-on, hop-off way to tour the area.
The 70-minute Gay Key West Trolly Tour, each Saturday afternoon from 4pm, is a great way to gain an appreciation for the island's queer history. Buy $25 tickets at the Gay Key West Visitor Center (513 Truman), or at many of the local LGBTA guesthouses. Pedi cabs are also increasingly popular on Duval Street and around Mallory Square. The operators with their sculpted calves often provide good eye candy.
What to See
Nearly all of Key West's gay bars and clubs are found within a few block of Duval Street in Old Town.
The Southernmost Point monument at the intersection of South and Whitehead Streets is an essential part of Key West's tourist kitsch that is a must see for anyone who has never visited the Conch Republic.
Literature aficionados will appreciate the Ernest Hemingway Museum (907 Whitehead St; 305-294-1136) and the more than 60 polydactyl cats that live on the property. Gay playwright Tennessee Williams also bought a small house here, at 1431 Duncan Street.
One of the more enjoyable (and relaxing) attractions is the Key West Butterfly & Nature Conservatory (1316 Duval St; 305-293-9358).
Old Town: The vast majority of Key West's gay-owned businesses are located in Old Town. Bustling Duval Street, which stretches from the Atlantic Ocean to the Gulf of Mexico, and Truman Avenue are among the area's main drags.
Media & Resources
The Q Magazine, Key West's monthly gay guide, has events listings and community news. Their online edition can be read page by page. Mark's List also covers Key West from their Fort Lauderdale home town.
The Key West Citizen routinely covers the island's happenings, both gay and straight.
Gay Key West, the local gay business association, has a Visitor Center at 513 Truman, and an informative tourist website, with the scoop on events that include: the March-April Gay Spring Break; the Key West Pride festivities in June; Tropical Heat each August; Womenfest in September; and the October Headress Ball. See them also about their Saturday 4pm trolly tours, departing from Duval Street at Angela.
The local website Keywestcocks.com is not about roosters.
For map locations and website links to the businesses below, and more, see our gay Key West listings pages.
Michael Lavers -in focus:
Oops! There went my swimsuit!
Key West's location near one of the hemisphere's largest coral reef systems has made it a popular destination for snorkelers, scuba divers and other nature enthusiasts for decades.
And what better way to experience nature than to go au natural?
Captain Steve Silva and his crew on the Blu Q catamaran offer a variety of cruises departing several times a week from their mooring in Key West's harbor.
A recent snorkeling trip brought more than 20 men to a small patch reef near Man Key. Among the eelgrass and clumps of brain and fan coral they spotted several species of tropical fish and even a barracuda.
A moon jellyfish stung one passenger who had apparently failed to heed the first mate's repeated warnings to avoid them. The sting left visible marks on his arm, but some vinegar was enough to temper the discomfort.
Jellyfish aside, one of the most enjoyable aspects of the cruise is the trip itself. The turquoise waters that surround Key West are some of the world's most tranquil (except when hurricanes periodically blow through the Florida Keys.) A handful of flying fish that skipped across the surface and a sea turtle captivated passengers on a recent tour.
One of the most enjoyable aspects of the trip is the visit to a sandbar. Passengers can explore using a sea kayak or simply frolic in the shallow tropical waters. Out gay radio host Frank DeCaro and his partner Jim Colucci had a particularly difficult time with the sea kayaks they tried to use on a recent trip.
"It was like skiing on the bunny slope, but thrilling none the less," he joked.
The remains of a raft on which Cuban migrants sailed across the treacherous Straits of Florida earlier this year are clearly visible on nearby Woman Key, but the vast majority of passengers remained focused on their various beverages and a handful of hunky Italians who captivated nearly everyone on board.
On a separate trip last October, I finally found enough courage to get naked. In one particularly embarrassing scene, I jumped after I spotted what I thought was a stingray swimming along the bottom -- it was, in fact, my swimsuit floating in the water.
Alexander's Guesthouse (1118 Fleming St; 800-654-9919), upscale rooms for gay men and women, pool and Jacuzzi, lush tropical gardens.
Big Ruby's Guesthouse (409 Appelrouth Lane; 800-477-7829), super deluxe accommodations, lagoon pool, chef’s prepared breakfast. well-heeled gay men and lesbians.
Caribbean House (226 Petronia St; 877-296-0999), Parisian-owned, five-minute walk from Duval Street, gay-friendly budget choice, ten no-frills rooms, all the amenities.
Coral Tree Inn/ Oasis Guesthouse/ Coconut Grove Guesthouse complex (822/823 Fleming St; 800-362-7477), Key West's largest gay resort, sophisticated and international with spacious rooms. Oasis and Coconut Grove guesthouses connected by garden pathway, have balconies and sun decks for luxurious, secluded relaxation; hot tubs, pools, afternoon "social." Quieter Coral Tree Inn has cool marble floors, and a pleasant pool area.
Curry House (806 Fleming St) historic 1889 B&B, nine guest rooms, full, hot country breakfast, heated swimming pool, indoor or outdoor seatings, library/lounge, WiFi, cable TV.
Equator Resort (818 Fleming St; 800-278-4552), all-male, postmodern digs, clothing-optional; designer fabrics, feather pillows, Italian-tile whirlpool baths, phones with voicemail, free Wi-Fi. Full continental breakfast by the pool, theme parties each season and resort-wide music keep guests entertained.
Fleming Bed & Breakfast (822/823 Fleming St), 20 adult-only rooms and suites, private sundecks, swimming pool, hot tub, huge Jacuzzi, breakfast buffet. Former Oasis Resort.
Island House (1129 Fleming St; 800-890-6284), all-male, green-in-every-which-way, sexual heat hot as Key West sun. Full gym, steam room, sauna, heated pool, two Jacuzzis, cafe and bar; clothing optional, massage, erotic video lounge, and restaurant. For guests and day-pass visitors.
New Orleans House (724 Duval St; 888-293-9893), deluxe rooms overlook Old Town Duval Street, expanded back court Garden Bar, with two pools, large hot tub, huge sun deck and stand-alone cottages. It's part of the Bourbon Street Pub Complex, where gay Key West parties.
801-Bourbon Bar (801 Duval St), part of New Orleans House/Bourbon Street Pub complex, with bingo, karaoke, cabaret, 801 Girls drag performances.
Aqua (711 Duval St) dance club, frequent special entertainment, mixed crowd of men and women, gay and straight. Club doors open directly to Duval Street.
Bobby's Monkey Bar (900 Simonton St), locals' bar, friendly boys and girls, gay and straight, frequent special events. Happy hours noon to 7pm.
Bourbon Street Pub (724 Duval St, at New Orleans House) popular day and night gay club, 10am-4am gay club, with music videos, male dancers, garden & pool bar; Friday Stripper Battles, Saturday pool parties and amateur strip contests, Sunday T-Dance, sexy male dancers nightly, foam, men-only and clothing optional parties.
Island House Cafe & Bar (1129 Fleming St), guesthouse clothing-optional poolside full bar and restaurant, with service day and night.
La Te Da (1125 Duval St), 3-bar complex at guesthouse, restaurant, cabaret entertainment.
Mango's (700 Duval St), award-winning "Floribbean" American food and "Caribbean Cowboy Cuisine," seafood.
Pearl's Patio Bar (525 United St), LGBT guesthouse bar and grill popular with women, live music, karaoke, burgers.
Saloon One (514 Petronia), behind the 801 Bourbon, leather-Levi-fetish men's cruise bar, home to Key West Wreckers and Bone Island Bears.
Find over two dozen restaurant suggestions on our maps & listings page.
Shopping and more
Leather Master (418 Appelrouth Lane), edgy toy store for the adventurous, merchandise for adults of many sexual bents, harnesses, vibrators, cock-and-ball toys, or masks; plus a a sizable porn collection.
For wheels, get to gay-friendly Moped Hospital (601 Truman Ave) -no better way to get around town than on a scooter!
Skinny Dipper Cruises (website) offers "alternative pampered charters" that are clothing-optional. Up to six people are accommodated on their 27-foot yacht with plenty of gourmet food, stong libations and interesting men.
Towels Of Key West (806 Duval St), towels and robes to treasure all your life.
Truman Adult Books & Video (922 Truman Ave), books, DVDs, toys, lubes, private booths for your pleasure.