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12 best things to do in Key West

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David Sloan knows well the magic of Key West. In his book, Quit Your Job and Move to Key West, Sloan describes his journey from corporate America to the laid back life of Key West. That was in 1996, and he hasn't regretted one minute.

Of course, Sloan is not alone in his love for Key West. The southernmost city has been an alluring travel destination for visitors from around the world for more than 75 years. A great deal of those visitors have been and continue to be gay and lesbian.

Key West has a well earned reputation as a welcoming destination. It was the first American city to launch a campaign to encourage gay tourism, and its official motto is "One Human Family."

While not every visitor to Key West decides to make it his or her home like Sloan, they are almost guaranteed to fall under the island's spell.

More information on visiting Key West is available at and

Go south
Go south Troy Petenbrink

Go south

The Southernmost Point painted concrete buoy marking one of the extreme points of the United States is likely Key West's most photographed landmark. Created in 1983, the fact that the buoy is not actually the southernmost point of the U.S. (that honor goes to Ballast Key, a privately owned island south and west of Key West) does not deter hundreds of daily visitors from snapping pictures of it.

Southernmost Point
400 South Street
(305) 809-3700

Be a beach bum
Be a beach bum Troy Petenbrink

Be a beach bum

A common misconception is that Key West has no beaches. That is not true. Key West has a number of nice sand beaches. The beach at Fort Zachery Taylor Historic State Park - affectionately nicknamed Elizabeth Taylor Beach by the local gays - is one of the most popular. There is also Smather's Beach (the island's largest at approximately a half mile long) and Higgs Beach that are both on the easterny Atlantic Ocean side of the island. Adjacent to Higgs Beach is the Key West AIDS Memorial in remembrance of the more than 1000 people from Key West who have died of AIDS.

Fort Zachary Taylor Historic State Park Beach 
Civil War-era fort, national historic landmark
End of Southard Street
(305) 292-6713

Higgs Beach
Playground, dog beach and recreation site
Atlantic Boulevard, MM 1.5
(305) 292-4431

Smather's Beach
Boat ramp, picnic area, restrooms/showers, jet skis, volleyball
South Roosevelt Boulevard
(305) 296-2554

Hunt Hemingway
Hunt Hemingway Troy Petenbrink

Hunt Hemingway

The great American writer Ernest Hemingway's ties to Key West are legendary. Visitors have the unique opportunity to trace his life on the island. The main attraction is the Ernest Hemingway Home & Museum, where he resided with his second wife Pauline from 1931 to 1939. There are also Captain Tony's Saloon and Sloppy Joe's Bar that each lay claim as Hemingway's official watering hole. For more than three decades, Sloppy Joe's has hosted the annual Hemingway look-alike contest that is part of the island's Hemingway Days celebration. In addition, there is a permanent exhibit about Hemingway’s life in and impact on Key West at The Custom House Museum.

Of course, Hemingway is not the only literary giant to call Key West home. For more than 30 years, internationally renowned gay playwright Tennessee Williams lived in Key West. The Academy Award-winning film adaptation of Williams' play, "The Rose Tattoo," was shot on the island in the 1950s, and the Tennessee Williams Theatre opened in 1980 with the world premiere of his play, "Will Mr. Merriweather Return From Memphis?"

Taste the island
Taste the island Troy Petenbrink

Taste the island

Often a destination is defined by its food, and Key West is no exception. By far its most famous eat is key lime pie. The story goes that the dessert, made of Key lime juice, egg yolks, and sweetened condensed milk in a pie crust, was created by Key West sponge fishermen sometime in the 1800s. From then to now, key lime pie has become an island must have, and some of the best can be found at Kermit’s Key West Key Lime Shoppe, Key West Key Lime Pie Co., and Blue Heaven restaurant. Other Key West signature dishes are conch fritters (Half Shell Raw Bar and The Conch Shack)  and Key West pink shrimp (The Flaming Buoy Co. and Garbo's Grill).

Enjoy your accommodations
Enjoy your accommodations Troy Petenbrink

Enjoy your accommodations

There are plenty of hotels and guesthouses to meet nearly any taste in Key West. For those seeking a large full-service property, the Hyatt Key West Resort and SpaWestin Key West Resort, and Casa Marina Resort are excellent options; and are TAG Approved gay-friendly. Among the boutique properties that draw a predominantly LGBT clientele are Alexander's Guesthouse, Equator Resort (all male), and Island House (all male). There is also the New Orleans House (all male), which is part of Bourbon St. Pub.

Watch the sunset
Watch the sunset Troy Petenbrink

Watch the sunset

Key West's bolstering about being home to the best sunset in the world is not just a marketing gimmick. Oh, no. The sunsets in Key West rarely disappoint, and watching the sunset is practically the island's official sport. Every evening hundreds of visitors gather with locals in Mallory Square to watch the sunset into the horizon of the Gulf of Mexico. The ritualistic celebration includes unique street performers, musicians and food vendors. Another popular gather place is the Sunset Pier at the Ocean Key Resort & Spa. For a little added adventure a sunset cruise is also an option with Danger Charter's Wind and Wine Sunset Sail and the Schooner Western Union being two of the best.

Take a trolley ride
Take a trolley ride Troy Petenbrink

Take a trolley ride

Do you know where Pulitzer Prize-winning playwright Tennessee Williams lived in Key West? Or how about the site of The Monster, a popular gay bar in the 1970s and 80s? The answers to these and many more questions about of Key West's rich LGBT history and lore can all be found on the weekly Gay Key West Trolley Tour. The tour, one of the first LGBT city history tours and certainly one of the longest continually operating, is given every Saturday afternoon and takes approximately 70 to 90 mins.

Gay Key West Trolley Tour
Sponsored by Gay Key West & The Key West Business Guild in partnership with Historic Tours of America.
(305) 294-4603

Play in the water
Play in the water Troy Petenbrink

Play in the water

With the Atlantic Ocean to its east and the Gulf of Mexico to its west, Key West offers some of the best opportunities for water sports and play. Barefoot Billy's offers a fun jetski tour of the island, and Fury Water Adventures has some cool  "do -it-all" packages that include snorkeling, parasailing, jet skiing, water toys and kayaking. The Blu Q specializes in men-only catamaran tours, including a number of very popular clothing-optional sails.

Catch a different view
Catch a different view Troy Petenbrink

Catch a different view

Almost immediately after the U.S. Navy established a base in Key West in 1823, the need for a lighthouse to assure the safe arrival of vessels navigating the shallow, reef-laden waters off the Florida Keys. The current lighthouse opened in 1848 with a woman as its first Keeper; nearly unheard of during the 19th century. In 1969, the U.S. Coast Guard decommissioned the Key West Lighthouse since there was no longer a need for a full-time Keeper due to technological advancements.  Today, this sentinel of the sea stands as a museum dedicated to Key West’s maritime heritage. Visitors can walk up the 88 steps to the top of the lighthouse for amazing views of the entire island as well as explore the belongings, photographs, and words of the lighthouse Keepers and their families who lived a now obsolete, yet never forgotten, way of life.

Lighthouse Tower and Keeper’s Quarters
938 Whitehead Street
(304) 294-0012

Flirt with butterflies
Flirt with butterflies Troy Petenbrink

Flirt with butterflies

There are some 50 to 60 butterfly species from around the world, along with over 20 exotic bird species, all under a climate-controlled, glass enclosed habitat at The Key West Butterfly & Nature Conservatory.  Gay-owned, the conservatory is open daily for tours and has an expansive gift shop.

Key West Butterfly & Nature Conservatory 
1316 Duval Street
(305) 296-2988

Cruise around
Cruise around Troy Petenbrink

Cruise around

Just shy of 7.5 square miles, Key West is a fairly small island. Given its size, one of the best was to travel around the island is via a scooter or bike. Not only is it much easier to find parking for your scooter or bike, it is just a more fun way to see the island. Moped Hospital is great for scooters, and The Bike Shop is obviously the place for bicycles. It's also a good idea to see if you hotel offers deals for rentals or loaner bikes. 

Wet your whistle
Wet your whistle Troy Petenbrink

Wet your whistle

No judgement -- but Key Westerners know how to drink, and there are plenty of places to have a good cocktail (or three... or more) on the island. With the exception of Bobby's Monkey Bar, which draws mostly locals, the LGBT bars are concentrated on Duval Street. Here you will find Aqua (drag), Bourbon St. Pub (go-go dancers), 801 Bourbon Bar (drag), and Saloon 1 (leather/Levi). Also on Duval is La Te Da, which is home to international known female impersonator Christopher Peterson.