Key West: a sub-tropical paradise

by Michael K. Lavers
National News Editor
Tuesday Oct 28, 2008

Located at the literal end of the road, Key West remains a low key sub-tropical paradise that offers gay visitors a welcome respite from their chilly northern climes and a healthy dose of off-beat attractions and hedonism to counter the hordes of cruise ship passengers who descend upon Mallory Square and surrounding streets each day.

Duval Street is the proverbial hub of Key West, but beautifully preserved Conch and shotgun homes, quiet streets, lush tropical gardens and sophisticated guesthouses are a short stroll away from the myriad of tonky bars, clubs, clothing-optional roof decks and boutiques.

So grab a rum and coke or another preferred fruity drink and explore what makes Key West such a fascinating sub-tropical paradise!

Fantasy Fest

Fantasy Fest, a 10-day festival held each October in the days leading up to Halloween, rivals Mardi Gras with its outrageous costumes, beads and locals who are all too quick to show off their local Conch assets. The festivities kick-off at La Te Da (1125 Duval St.) with the annual Fantasy Fest King and Queen coronation and fundraiser for AIDS Help, a Key West-based organization that provides services to people with HIV and AIDS throughout the Florida Keys. Other events include the Headdress Ball at the Southernmost Hotel (1319 Duval St.) and the Pet Masquerade, but the festivities reach their apex with an estimated 70,000 people packing Duval Street to watch the Fantasy Fest parade. This year’s theme was "Pirates, Pundits and Political Party Animals," and more than one MILF found their inner Sarah Palin in Key West this year!

Other festivals held throughout the year include WomenFest in early September, Tropical Heat in August and Gay Spring Break from late February through mid-April. Goombay, held in Bahama Village at Duval and Petronia Streets, showcases the island’s Caribbean history. The marinated kabobs, arepas and empanadas with a glass of local beer are particularly tasty.

Key West also garners an extra 15 minutes of fame each New Year’s Eve with Sushi dropping onto Duval Street in a giant red stiletto at midnight. She told EDGE in a recent interview at 801 Bourbon Street (801 Duval St.) the tradition began a decade ago after the bar’s owners insisted she usher in the new year in a shoe. Chicken wire and paper mache held the original shoe together, but this Key West drag kitsch has attracted coverage from Anderson Cooper, the Associated Press and even the New York Times.

"It’s a tradition now in Key West," Sushi said.

Gay Guesthouses

In addition to Sushi, Key West lays claim to some of the best gay-owned and operated guesthouses in the country. The Island House (1129 Fleming St.) features 38 rooms and apartments. It contains a swimming pool, bar with free happy hour for guests from 5:30 - 7 p.m. each day and a restaurant surrounded by lush tropical gardens. The clothing-optional resort also features an indoor and outdoor Jacuzzi, sun deck, gym and a video room locals have affectionately dubbed the "cultural room."

The Island House is located on "Guesthouse Row" in Old Town in close proximity to the Equator Resort (818 Fleming St.), the Coconut Grove Guest House (817 Fleming St.) and other gay-owned and friendly hotels and bed and breakfasts. Others include Big Ruby’s Guesthouse (409 Applerouth Lane), Cypress House (724 Duval St.) and the oceanfront Reach Resort (1435 Simonton St.). Pearl’s Window (525 United St.) caters to women.

The vast majority of these guesthouses are less than a 10 minute walk from Duval Street’s bars and clubs. Many of them were surprisingly quiet in the days leading up to this year’s Fantasy Fest, but a rowdy mix of locals and visitors welcomed Porsche back to Bourbon Street Pub (724 Duval St.) after spending the summer on Fire Island on a recent Tuesday. Nearby Aqua Nightclub (711 Duval St.), KWEST Men (705 Duval St.) and the new cabaret and piano bar The Keys (1114 Duval St.) provides the perfect pink bar crawl.

Local Eats

Originally named Cayo Hueso (Bone Key) by Spanish explorers because of the numerous burial grounds they found, Key West has drawn gay men, lesbians, Bahamians, Cubans, pirates, snowbirds and a myriad of others over the centuries. And local cuisine certainly reflects this demographic diversity.

Mangoes Restaurant (700 Duval St.) provides a strategic location to watch bikers, drag queens, fanny-pack clad tourists and of course locals stroll up and down Key West’s main drag over grouper, a mushroom martini and a steady stream of fruity drinks. Azur Restaurant (425 Grinnell St.) offers a variety of Mediterranean cuisine that includes seafood and shellfish. The seared jumbo sea scallops with a sweet pea puree, marinated tomato, cucumber and red onion salad is particularly good. El Siboney Restaurant (900 Catherine St.) offers copious portions of puerco asado (roast pork), sangria and other Cuban dishes in a family-style setting.

Croissants de France (816 Duval St.) has an extensive selection of freshly-baked rolls and baguettes, crepes and omelets for breakfast. The Coffee Plantation Key West (713 Caroline St.) near the Sea Port is a great place to grab a coffee or espresso and check e-mail. And Denny’s (925 Duval St. at Truman Avenue) is the perfect place to grab those late-night French fries for that drunken stroll home or post-trick walk of shame.


In addition to its food, Key West and its surrounding turquoise waters offer a literal bounty of outdoor activities. Snorkeling around the island has become something of a clich?, but the clothing optional Blu Q (201 William St.) cruise is a uniquely gay trip. Native Texan Capt. Steve takes passengers snorkeling among coral heads on his 600 square foot catamaran. He and his crew provide lunch, free soda, beer and wine during the five hour trip. And passengers are allowed to frolic on a sand bar between Ballast and Woman Key. Imagine 20 drunk and naked gay men in the Gulf of Mexico! Captains Karen Luknis and Debra Butler of Venus Charters (2210 Staples Ave.) offer similar trips for lesbians on their 25 foot Proline.

Dry Tortugas

For those seeking something more remote, the Dry Tortugas National Park is perhaps the best bet. Located nearly 70 miles west of Key West, the small archipelago contains the Civil War-era Fort Jefferson. Doctor Samuel A. Mudd called this installation, which doubled as a prison, home for nearly four years after a court found him guilty of conspiracy for setting John Wilkes Booth’s broken leg following Abraham Lincoln’s assassination. Visitors can snorkel among the coral and tropical fish along the fort’s protective moat. And they can even camp on Garden Key, the island on which the fort is located, for a nominal fee.

The Yankee Freedom (240 Margaret St.) is one of two catamarans that ferry visitors to the island each morning (sea planes also shuttle visitors to the park.) It leaves the Sea Port at 8 a.m. and arrives at Garden Key around 10:30 a.m. The crew provides a continental breakfast and a picnic lunch upon arriving at Garden Key. A guided tour of Fort Jefferson is also available, but not advised. The catamaran leaves the island around 2:45 p.m. and returns to Key West around 5 p.m.

Museums and Cats

Back on land, Key West offers a variety of gay and non-gay attractions that are worth at least a brief look. The Gay and Lesbian Historic Trolley Tour leaves from the City Hall parking lot (Angela and Simonton Streets) each Saturday at 10:30 a.m. Guide Curry provided passengers a steady stream of all too obvious gay Conch jokes, but the 70 minute tour is a good way for those who have never been to Key West to get their bearings.

Ernest Hemingway’s house (907 Whitehead St.) is a must see for anyone who wants to follow the troubled writer’s trail or any lesbian who wants to see the dozens of six and seven-toed cats that live in and around the property. The Key West Butterfly and Nature Conservatory (1316 Duval St.) provides a relaxing respite from Duval Street’s hustle and bustle, while the Mel Fisher Maritime Museum (200 Greene St.) showcases the cache of gold, silver and other artifacts its namesake recovered upon discovering the wreck of the Spanish galleon Atocha in 1985.The 60-foot tower at the Key West Shipwreck Historeum Museum (One Whitehead St.) provides sweeping views of Old Town.

Key West has weathered hurricanes, a slumping economy and even the influx of cruise ship passengers (and their kids) in recent years, but the four by two-mile island at the southern terminus of U.S. 1 remains a largely attractive destination.

Long-time Key West resident Carol Shaughnessy perhaps sums it up best.

"It’s an incredible town," she said over a recent breakfast at Big Ruby’s Guesthouse. "If you are meant to be here, it will not let you go."

Key West is located about 160 miles southwest (or roughly three hours by car on the Overseas Highway) of Miami. Flights to Key West International Airport are available from Atlanta, Charlotte, Fort Lauderdale, Miami and other Florida cities. Log onto for more information.

Based in Washington, D.C., Michael K. Lavers has appeared in the New York Times, BBC, WNYC, Huffington Post, Village Voice, Advocate and other mainstream and LGBT media outlets. He is an unapologetic political junkie who thoroughly enjoys living inside the Beltway.


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