The key to fun

5 amazing ways to enjoy our own island paradise of Key West

Long before marriage equality reached the shores of America, Key West was out before being out was in.

This little island at the far end of the Florida Keys has a long history of welcoming LGBTQ, dating well back into the last century.

There is some remarkable history here: Richard Heyman, mayor of Key West in the 1980s, was one of the first openly gay elected political officials in America. As recently as the 2018 election, Key West voters elected Teri Johnston as mayor, making her the first openly lesbian mayor of any city in Florida.

The liberal spirit of the island keeps welcoming visitors in new and creative ways over the decades.

Here are some great ways to enjoy the unique spirit of Key West while shining as bright as the endless Florida sun.

1. Beaches & bods

Two shirtless men smile on a bike in Key West.

Enjoy the beautiful weather Key West offers year-round, and join the tens of thousands of people gather in Key West for major street festivals like FantasyFest and Key West Pride.

These parties are all about enjoying the great outdoors, with sexy costumes and body painting displayed across the spectrum of (adult) humanity. For those people who want to enjoy the sun in beachwear, Key West boasts multiple white sand beaches, with public access lining the southern shore. Hotels have created their own beaches elsewhere on the island, which are available to guests. (Insider tip: Enjoy lunch or dinner at your resort’s restaurant, then take a stroll on the private beaches after.) LaTeDa Hotel, Alexander’s House, New Orleans House, Equator Resort Key West, and Island House all have lovely pools, and some are clothing optional. The Island House and Equator Resort Key West encourage you to lounge in all your glory.

2. Nightlife adventures in Key West

A drag queen hosting a New Year's Eve part in Key West, with a big red shoe in front of the word 2016.

Drag culture also has deep roots in Key West, and you’ll find queens running amok hosting parties on a regular basis. Cabarets such as the show at 801 Bourbon Street and Aqua are not be missed. Neither is local icon Qmitch Jones, who hosts fabulous weekly events. Toss on a wig and some glitter, and join in the revelry. (The very gay part of Duval Street starts mid-island and extends south.) On New Year’s Eve, the final countdown (pictured, above) is commemorated by dropping a local drag queen in a giant red shoe.

3. Private pleasures

Key West isn’t just about street parties and lounging by the pool. Hotels and spas, including Sunset Key Cottages (photo above), provide settings for privacy and romance, and there are plenty of fine dining restaurants perfect for commemorating special occasions. Azur Restaurant owners Drew and Michael dote on their customers like family, and Blackfin Bistro owners Joseph and Michael have a refined take on classic bistro cuisine (try the Wagyu burger).

4. Island exploration

Not everyone can relax lounging all day by the pool, and there are plenty of options for the active traveler. Rent a bicycle for a ride around the island, to see the historic architecture and the home-made art displayed in local residents’ front yards. Deep-sea fishing, sailing and jet skiing are a short boat ride away from the port. Captain’s Corner Dive Center, the lesbian-owned scuba company, escorts divers to Florida’s coral reefs and shipwreck sites that have become homes to sea life. For snorkeling or a tranquil sunset sail, Blu Q Catamaran offers all-male (clothing optional) cruises on a sailboat that cruises to swimming spots for viewing wildlife and splashing in the warm deep blue sea.

5. Tie the knot in Key West

Thanks to legalized marriage equality, Key West is now the ultimate wedding destination: Step onto Duval St. for a raucous bachelor or bachelorette party, and then the rest of the island awaits with spectacular locations to stage a unique ceremony. Popular spots include Smathers Beach, where the sunset paints a beautiful backdrop, and the garden oasis of the West Martello Tower, a former military fort. Fun fact: one of the island’s top wedding caterers, Dustan Carpenter, is known as the “Pickle Baron” thanks to his famous array of artisanal pickles he prepares with his partner.

Only in Key West.

Photos courtesy of Visit Key West

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