A shocking sight in Key West, even for a San Franciscan

January 3, 12:33 PMSF Gay Travel ExaminerEd Walsh

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Palm Tree in Key West. (Photo by: Ed Walsh)

It was a Key West moment that was enough to shock this San Franciscan.

I entered the 801Bourbon Bar on a Sunday afternoon.  It was during my first day on the island at the southernmost tip of the continental US.  I followed in the wake of another man through a curtain to another bar in back of the main bar.  There was a small group of people at the bar and a man playing pool -- in the nude. 

While playing pool in the nude may get you thrown out of a bar in San Francisco, it doesn’t raise an eyebrow in Key West.  It’s just part of another day in the live and let live vacation island paradise just 90 miles from Cuba.
 
The Bourbon Street Pub Complex, along Key West’s main drag, Duval Street, is  at the gay center of nightlife in Key West.  If you watched CNN's New Year's Eve coverage, you saw the drag queen, Sushi, descending down from the Bourbon Complex's balcony inside a big high heel shoe.   YouTube video of  her welcoming  in 2009 is below.

The nightlife and gay vacation resorts that sprouted up like weeds in late 70s and early 80s were largely responsible for a renaissance in the city.  Before that rebirth 30 years ago, its floundering popularity was evident in the rundown and abandoned storefronts along Duval Street, in the center of downtown.  Locals like to tell the story of a Duval Street store owner who sold his business for $5, just to get it off his hands.  Some may question whether that is part urban legend but no one would question the city’s rags to riches resurrection. 
 

The girls pose in front of the 801 Bourbon Complex.  (photo by: Ed Walsh)

Key West has long been popular with gay men and lesbians even before gay author Tennessee Williams first called the city home in the 1940s.  But its popularity as a gay vacation getaway soared along with its real estate prices through the 80s and it continues today.
 

The Sights

 
Many people who have never been to Key West assume it’s all about the beaches.  It’s not.  You can have a great time Key West and never set foot on a beach.   There are a wealth of sights, museums and other attractions in the city that will more than occupy your time.  Your vacation won’t be dampened there even if it rains.
 
The best way to get the lay of the land in Key West is to take an Old Town Trolley or Conch Tour Train of the island.  By the way, the “train” is not a real train but a motorized open-air tram car pulled by a truck made to look like a train.  Key West hasn’t had a real train since a hurricane blew down the tracks north of the city in 1935.   The tours constantly ramble through the city.  I took a couple of the tours but neither mentioned anything about gay life or the gay history of the island.  But take heart, the Gay and Lesbian Historic Trolley Tour commences every Saturday at 11am  It will take you by places like Tennessee Williams’ house, that the main stream tours overlook. It will also go by the beach side AIDS memorial, which merited a passing reference from a mainstream tour. 

Below video of the Gay Lesbian Tolley Tour as it goes by the Southernmost Point.  The trolley is almost all women because it was shot during the annual Womensfest celebration. Video of a mass lesbian commitment ceremony at Pearl's resort follows.  Then, street dancing during Womensfest.

There are also some gay cruises, one is called the Blu Q.  It’s for gay men. There are a couple for gay women.  One is run by Sebago Key West.  It features a women-only champagne sunset cruise on Thursdays if you book on-line.  The lesbian owned and operated Venus Charters offers three-hour snorkeling and dolphin watching cruises that include a snack and beverages.  Venus excursions leave twice a day. 

Blu Q Sunset Cruise (Photo by:  Ed Walsh)
 
Probably the best-known sight in the city is the house that belonged to author Ernest Hemingway.  The house gives an interesting peek into Key West’s past.  You can wander through on your own, but it’s worth hanging around a few minutes for a guided tour.  I asked my tour guide about whether Hemingway had ever met Tennessee Williams.  He explained that they had, but just once, in the 40s in Cuba.  Williams, he said, was reluctant to meet Hemingway because he heard he was homophobic.  But the pair met and talked for about four hours, finding common ground sharing stories of each other’s aches and pains.
 
Other popular sights include the Key West Aquarium, the city’s landmark lighthouse, the Custom House Museum, the Mel Fisher Maritime Museum, and the Key West Shipwreck Historeum museum.

By the way, the shipwreck business became Key West’s biggest industry in the late 1800s. As a result, back then, the city boasted that it had the highest per-capita income of any city in the country.  The rules were that if you first helped save the people on the sinking boats, you could have a share of the property on the boats.  Key West is surrounded by a coral reef and ships would sometimes wreck as often as once a week.  By the 1930s, a perfect storm of the Depression and other factors sunk the city’s economy, pushing it from riches into rags.  The city’s shipwrecking industry began to die about twenty years before the depression with  the advent of better navigation devices.

No trip to Key West would be complete without having your picture taken in front of the over-sized land-locked buoy that marks the “Southernmost Point in the Continental United States.”  Technically, the southernmost point is a few steps father south on the US Navy base.  And some sticklers would argue that Key West is not really part of the continental US because it’s an island.  But dammit, it’s a good picture.

Don’t be alarmed if you see wild chickens everywhere in Key West.   After cockfighting was outlawed in the mid 20th century, many breeders simply let them run wild.  Around that same time, many people let their chickens run free because it became easier to buy chicken and eggs in a store.  The  chickens reproduced and multiplied and are now an institutionalized  Key West oddity.   The birds have developed a following among tourists, unless you are a tourist who is awakened at 5am by a crowing rooster.

The Pirate Soul Museum is a great crowd pleaser.  Bringing entertainment together with some fascinating history.
 
 Accommodations

Although there are fewer exclusively gay guest-houses and resorts in Key West than in the 80s, the island more than makes up for it in the quality and variety of accommodations for those who prefer a mostly gay environment.  Most gay guest-houses include a continental breakfast.  Room rates can vary greatly by season.  The low season rates generally kick in the late spring/early summer and last until just before Christmas.

Pearl’s Rainbow is not only the city’s only exclusively lesbian guest house, it contains Key West’s only exclusively lesbian bar.  The impeccably maintained upscale guest house complex has 38 rooms, two clothing optional pools, and is spread out among five buildings.  The main house once was a cigar factory.  This resort is first class all the way.

The largest gay guest house is a combination of three guest houses together, the Coconut Grove, Oasis, and Coral Tree, with a  total of 47 units.  The Coral Tree is on one side of Fleming Street and the Coconut Grove and Oasis on the other.  Guests have access to all three.  Each house has its own hot tub and pool.  In addition to a continental breakfast, amenities include free frozen drinks in the afternoon and more drinks and  hor d'oeuvres  in the early evening.  The quality of all three guest houses is top-drawer.  All are clothing optional.  If you like a crowd, the Oasis is the busiest of the three.  The Coconut Grove reopened better than ever in late 2006 after being completely renovated and updated following a fire.   The complex is among the very best gay resorts you will find anywhere in the world.

View from the Oasis Resort.  (Photo by:  Ed Walsh) 
 
The 38-room Island House has the highest sexual temperature of any of the city’s gay guest houses.   It’s open for day passes.   Amenities include a small but very well-appointed fitness room and free happy hour drinks. The Island House is as sexually charged as it always was but it is not the dump it was years ago.  The current owners completely redid the rooms and common areas making it one of the highest quality guest houses, gay or straight, that you will find anywhere on the island.   Even if you are not staying there, its poolside restaurant is a great place to stop for a meal in a unique, all gay male environment.  And the restaurant is now open 24 hours!  This wonderful property has it all in one place.

The 17-room Alexander’s Guest house is across the street from the Island House.   Those who appreciate good design will find a lot to love about the Alexander.  The rooms and the lobby area look like something out of a design magazine. It is mostly gay male but it enjoys some lesbian clientele.  It is clothing optional on the sun decks on the second and third level but not on the first floor pool level.  It includes a breakfast with freshly made baked goods.  They serve the best French toast you will find anywhere!  It's right across the street from the Island House and they offer discounted passes to that property if you want to walk on the wild side but sleep in a more tranquil environment. 

YouTube video of suite at the Alexander Guest house below.

 
The 22-unit Big Ruby’s is one of the oldest gay guest houses in Key West.  It is also gay/lesbian integrated with women making up five or ten percent of the guests.  Big Ruby’s amenities include a fitness room, free happy hour drinks, and a hot cooked to order breakfast.  Big Ruby's is the place if you want to be closer to downtown.  But the property itself is a wonderful oasis that feels like it is miles from civilization.   
 
The 19-room Equator guest house is next door to the Coral Tree and is also exclusively male.  It also provides a free continental breakfast and free daily happy hour.  The quality of the resort is among the finest that you will find anywhere.  
 

The fabulous Equator Resort.  (photo by: Ed Walsh)

 
The 10-room New Orleans House is a perfect spot for gay male visitors who want to be smack dab in the middle of all the action.   It’s upstairs from the Bourbon Street Complex bar and its pool is part of the complex’s garden bar, giving guests an opportunity to see a lot of new faces every day at the pool.  Its room rate includes two free drink coupons every day.  It does not include breakfast but there are a wealth of places to eat just steps away. 

Nightlife
 
The Bourbon Street Complex includes two buildings across the street from each other.  Each has three bars.  The 801 Bourbon bar on 801 Duval Street is a storefront bar and mostly men.  The One Saloon is entered through the curtain in the back and is primarily a Levi/leather crowd.  It’s also where I found the aforementioned naked pool player.   Nightly drag shows, a Key West tradition, are in the cabaret space upstairs.  Across the street, you will find the  Bourbon Street Pub with video and some of the hottest dancers in Key West.  A poolside garden bar is behind the pub.
 
A block away from the Bourbon Street Complex, on 705 Duval, you will find the Kwest bar.  Since 2003, totally nude bar stripping has been legal in Key West and Kwest is where the men bare all.  
 
You will find the expansive Aqua nightclub just a few steps from Kwest on 711 Duval.  It features a 3-8pm happy hour, dancing, and drag shows.  It’s lesbian-owned and gay/lesbian mixed.
 

Bobby’s Monkey Bar on 900 Simonton Street is a little off the gay beaten path and is a popular local bar with both lesbians and gay men.
 
The aforementioned Pearl’s complex on 525 United Street, just off Duval,  is home to Key West’s only exclusively lesbian bar, Pearl’s Patio.

The La Te Da hotel and bar are a must stop on Sunday afternoons starting at 4 p.m. for the tea dance.
 

Alice's Restaurant, sadly, is no more.  In its place you will find The Keys,  a wonderful piano bar.

Restaurants

 
Despite its laid back beach reputation, you will find no shortage of fine dining in Key West.
 
The gay-owned award-winning Square One restaurant on 1075 Duval Street features a fine-dining restaurant and a next-door café that’s open for lunch and dinner.
 
Antonia’s is another gay-favorite.  The 21-year old restaurant on 615 Duval Street is close to the gay center of town and you will find some of the best Italian food you will  find anywhere there.

And don't forget, the Island House now has a 24-hour restaurant.
 

Getting there and around

     
Don’t rent a car.   Parking and traffic can be challenging downtown even in the low season.  The best way to get around to see all the sights and the clubs is by bicycle.   Most guest houses have bikes available for rent and there are a number of bike rental places throughout the city.  
 
Fares to Key West haven't been this low in a long time.  I found a fare recently for $335 round trip from SFO.