Despite a devastating hurricane season, the legendary gaystination at the edge of the U.S. thrives

Gay businesses in Key West escaped the wrath of Hurricane Irma virtually unscathed. The city’s four LGBT hotels, as well as the island’s gay bars and nightclubs, suffered only minor damage. As of late last month, tourism officials estimated that 92 percent of the city’s hotels (including neighboring Stock Island) were back in business, while the Keys overall linger around 80 percent. Still, the hardest-hit area of the Keys was a 30-mile stretch that began about 10 miles northeast of Key West up to the west end of the Seven Mile Bridge.

If you have thought about visiting Key West for the first time, or are considering a return visit, now is actually the ideal time. Besides having a great time in the gayest of gaystinations, you will be helping support the jobs and the livelihood of not just those in Key West but those who commute from the northern Keys and depend on Key West tourism to support themselves.

For many residents, the happiest sight was the arrival of the first cruise ship to the island on Sept. 24, two weeks after the hurricane. (Key West officially opened for tourists Oct. 1.)

You will find few signs of Irma’s wrath today. The city banded together early on to clear out debris. Most homes and businesses that were damaged by the hurricane were quickly repaired. All of the city’s landmarks are up and running. The only evidence of Irma I noticed was the observation tower at Shipwreck Museum that appeared in good condition but remained closed apparently until further repairs could be made.

The neighbor-helping-neighbor community spirit for which Key West is famous undoubtedly boosted the city’s fast recovery.

And with a large gay community, it is no wonder that people simply would not tolerate the city looking unkempt.

Lighthouse

Climb the Key West Lighthouse, which is across the street from the Hemingway House.

Key West is used to pulling itself out of tight corners. The shipwrecking industry first put the city on the map in the mid 1800s.

By 1856, that industry made it the richest city per capita in the United States. The rule of shipwrecking is that you could keep a good portion of what you salvaged from ships as long as you saved the people first.

But better navigation systems that kept ships from crashing on the coral reefs, combined later with the Great Depression in the 1930s, transformed Key West into one of the most impoverished areas in the country. In the mid-1970s, the U.S. Navy scaled back its local presence, causing another big hit to the island’s economy. Gays were a big part of the city’s revitalization in the ’70s as they bought up and fixed up some of the island’s abandoned buildings and businesses.

By the 1980s, the city had emerged as one of the most upscale destinations in Florida. The modernization and urban renewal movements of the 1950s and 1960s passed Key West by, so much of the charming architecture in the city remains.

Gay stays
In truth, Key West has evolved in the scope of its appeal. While many of the former gay resorts here have gone straight or “all welcoming,” what the city lacks in quantity, it more than makes up for in the quality of its remaining guesthouses. The Island House justifiably tops many lists as the best gay resort in the world; it stays busy even in the hurricane season. With 39 rooms, it is the largest gay resort on the island, and it’s not uncommon for regulars to check in and leave the property only rarely. The clothing-optional, men-only resort doesn’t charge a resort fee but offers guests a long list of freebies, including four alcoholic drinks a day during its late afternoon/early evening happy hour. Other amenities include cafe and bar that never close, a small but well-appointed gym, wet and dry saunas, indoor and outdoor hot tubs, sundeck patio, porn video playroom and a large swimming pool. It’s open for day passes so it is a good place to mix it up with locals and fellow travelers alike. If you are on budget, the upscale resort has some rooms that have a shared bath at a cheaper rate than the standard rooms. Island House also offers a deal that if you stay at least four nights over the winter, you get three summer nights free.

The upscale Equator Resort, just down the street from the Island House, is another first-rate property. The 34-room guesthouse is also a men-only clothing-optional resort. A few years ago it combined with the former Coral Tree gay guesthouse; as a result, it offers two pools and two hot tubs. The Equator also includes a continental breakfast, free WiFi, and a free cocktail hour. It does not offer day passes, though, giving it a more intimate feel than the Island House.

Alexander’s Guesthouse is an upscale LGBT hotel that is the place to be if you prefer a quieter stay. It is across the street from the Island House and offers discounted day passes, so you can have the best of both worlds. Although its clientele is mostly male, the property has a good share of lesbians and open-minded straight people. One of the hotel’s sundecks is clothing optional but the pool and other parts of the property require a bathing suit. It includes a deluxe continental breakfast and a free happy hour. The hotel is open only to those 21 and up.

If you want to experience Key West’s lively gay nightlife but don’t want to stray too far, the world-famous New Orleans House is a good bet. The 17-room gay men’s clothing-optional hotel is on Duval Street, in the heart of the city’s gay nightlife block over the Bourbon St. Pub. It includes a continental breakfast. Its pool and hot tub are part of the Garden Bar, which is clothing-optional and right behind the main Bourbon St. Pub. It also includes a well-equipped gym that is free for guests and non-guests alike. The New Orleans House has a patio deck for guests with the best people-watching in town. Drag Queen Sushi descends from the ceiling on giant high-heeled shoe each New Year’s Eve in a tradition that is usually covered live by CNN.

Nightlife
The Bourbon St. Pub includes a main open-air bar that fronts Duval Street. It has strippers who can often be seen beckoning customers in from the sidewalk. Depending on the night, you can also see live shows and karaoke there. The aforementioned Garden Bar is right behind the Pub. Like the name implies, it is an outdoor open-air bar in a garden with an adjacent pool, jacuzzi and sundeck. The Garden Bar space is clothing optional and open to men only.

PoolThe 801 Bourbon Bar is kitty-corner from the Pub and is appropriately located at 801 Duval St. It is famous for its upstairs cabaret bar featuring Key West’s legendary drag queens. The downstairs bar is always fun, and if you want to walk on the wild side, the One Saloon is right behind the main bar and is popular with the Levi/leather crowd. It has a pool table and is known for its infamous Friday night contests.

A block away on Duval sit a trio of connected nightclubs: Aqua, the Back Bar and the Side Bar. Aqua is famous for drag shows and live entertainment. The Back Bar is so named for its location behind Aqua. You can enter through Aqua or the side alley. It is an open-air space perfect for socializing while enjoying the warm Key West evening breezes.

Key West’s newest bar is Side Bar, the modern space on the side of Aqua. With the closure of Pearl’s years ago, there are no longer any full time lesbian bars in Key West but Side Bar has a women-popular “Hot Dog Church” on Sunday afternoons that serves up hot dogs for an old-fashioned cookout social. Lesbians take over for a week during Womenfest, which will be held Sept. 5–9 this year. Many of the mostly men’s bars will yield to women that week.

La Te Da on Duval, just down the street from the Bourbon Bars, is known for its nightly cabaret and drag shows and is famous for its early Sunday Evening Tea Dance.

The Monkey Bar is on Simonton Street, which runs parallel to Duval. The bar is off the beaten tourist path making it popular with locals who enjoy the bar’s nightly karaoke show. A mural on the side of the bar depicts the quirkiness for which Key West is known: It depicts Wilhelmina Harvey’s crossing of the Seven Mile bridge into Key West. The late Ms. Harvey was a Key West character who spearheaded a satirical separation of Key West from the rest of the U.S., known as the Conch Rebellion. The mural is patterned after the depiction of George Washington crossing the Delaware River. One of the conch loyalists is shown displaying the rainbow flag.

Attractions
The best place to get one-stop information on Key West attractions, both LGBT and mainstream, is the city’s new LGBT Business Guild storefront, which opened this fall, just after Irma. The center at 808 Duval St. includes a list of daily activities related to the LGBT community as well as information on mainstream tours and attractions.

One of the city’s newest attractions is a museum dedicated to gay playwright Tennessee Williams. It is at 513 Truman Ave. (U.S. Highway 1). Before the LGBT Business Guild moved its offices to Duval Street, it shared the space with a much smaller Tennessee Williams exhibit. The new museum has taken over the whole space and dedicated it to the author’s life and work. It also includes a dollhouse replica of his home on Duncan Street, which is a private home and not open for tours.

Key West’s long-running Blu Q is a catamaran touring company that runs a number of excursions marketed to LGBTs, including a sunset tour and all-male, clothing-optional half-day tours. Blue Q is a great way to explore the waters around Key West with family.

The most photographed attraction in Key West is a buoy-shaped monument at the island’s Southernmost Point proclaiming it is just 90 miles to Cuba. But if you want to get precise, the Southernmost Point is 88 miles to Cuba and the actual Southernmost Point is the Naval Station adjacent to the buoy, which is just a little further south but off-limits to civilians.

A good way to get the lay of the land in Key West is through a number of bus or open-air tram tours of the island. The tours start near the beginning of Duval Street, where it meets Front Street along the waterfront. Most of the tours allow you to get on and off at anything you want to see.

East coasters are not used to seeing the sun set over the ocean, so it is not surprising that sunset is a big deal in Key West.

People gather at the Mallory Square waterfront promenade every night to watch the sun go down. The square is lined with street performers and food stands and local artisans.

Of course, aside from Tennessee Williams, Key West’s other famous writer-in-residence was Ernest Hemingway. His house is open for tours daily. Across the street from Hemingway House is the city’s historic lighthouse. If you don’t have vertigo, you can walk up the winding, narrow staircase to the lookout at the top of the tower. The keeper’s house next to the lighthouse is a museum that gives great insight on what it was like to live in Key West in the 19th century. The city’s old Custom House, now a museum, includes a section devoted to Williams’ paintings.

The waterfront is also home to a couple of museums dedicated to the shipwreck industry, but its oldest running attraction is the

Key West Aquarium. A much-less traditional museum, the Ripley’s Believe It or Not museum includes oddities from around the world and a few from Key West.

Key West’s gay community was hard hit by the AIDS epidemic in the 1980s and 1990s. A touching AIDS memorial stands on the start of the Edward B. Knight Pier where White Street dead-ends into the ocean. It includes the names of residents lost to the disease.

There are a couple of beaches near the AIDS Memorial, but a favorite is at Fort Zachary Taylor Historic State Park, which gays had dubbed the Elizabeth Taylor Park. The park includes a military fort that dates back to the civil war and has picnic tables and shade trees.

Getting there and getting around

A rental car is more trouble than it is worth in Key West. Parking is sometimes challenging. The best way to get around is by bicycle. You can rent a bike on the island for as little as $10 a day, and even less if you rent by the week. 
Scooters are also popular.

Several airlines run connecting flights from DFW to Key West. You can fly on American or Delta with connections in Miami or Atlanta in about 4.5 hours.

— Ed Walsh

For more photos of Key West, click here