What is it about the country’s most remote corners that attracts the curious, creative, and independent? Key West is the best destination to understand the alchemy of these magical escapes and why they, and especially Key West, have become havens for the gay community.

There’s something to being as far away as possible from your reality, while still knowing your day-to-day is within reach. In Key West, you’re closer to Cuba than to mainland Florida, so you’re as far south in the US as you can get without needing a passport. Knowing that you’re at the edge of life, does set you free. So too does the inspiring qualities of light and water that make Key West—and those who visit—sparkle.

It is no surprise, thus, that luminaries of literature, art, music, politics, and sport are drawn to or are from Key West. From Ernest Hemingway and Truman Capote to Harry Truman and Winslow Homer to Jimmy Buffet and Diana Nyad, this tiny little corner of the country has had a massive impact on the rest of the country and world. It is here where people come to clear the mind and set forth a vision, free of judgement and full of support. To be here, is to be who you are.

And become who you are with. The people of Key West hold you close, make you feel at home, and see you as you are, because most likely, they are like you, too: open, curious, and kind. It makes infinite sense that Key West lives by the philosophy “One Human Family.”

So, when it comes time for you to step further towards who you are meant to be and join this family, here’s how we recommend you experience Key West.

Where to Stay:

Pier House Resort: This 70s icon, host to Key West’s creative set over the decades (it is here where Jimmy Buffet first performed), still welcomes one and all to its seaside rooms, stellar spa, and classic Key West décor.

Island House: All the amenities of a large-scale resort and all the high-touch hospitality of a boutique hotel, Island House is the perfect gay gents resort. Newly renovated, Island House still boasts of great personal service, rollicking happy hours, and an option to bare it all.

The Perry Hotel Key West: Tucked away on Stock Island, a stone’s throw from Key West’s eastern shore, this naval inspired ‘all-welcome’ boutique hotel is all about its balconies overlooking the water and mangroves, chic pool area, and overall design (named on of AD’s best new designed hotels).

Equator Resort: Leave your clothes in the closet at this beautifully designed and landscaped men’s only, clothing optional resort. The rooms, pool, and public spaces only pale when compared to its incomparably friendly service.

Note that, depending on your vibe there are countelss other places to stay in Key West, from clothing optional, male only if you’re on that vacation journey, to outposts of larger chains like Hyatt and Kimpton if using and gathering miles is your mission!

What to Do:

Visit the Literati and Iconic: Make a morning of a visit to Tennessee William’s Home and commune with the spirit of one of the first celebrities to live fully out in the 1940s and beyond. By counterpoint, visit Ernest Hemingway’s manse(the first in Key West with a pool!) where he penned, among other masterpieces, A Farewell to Arms. Then, stop across the street for a visit to the Key West Lighthouse and Keepers Quarters. July is a fun time for these visits as they’d coincide with the Hemingway and the Key Lime Festivals.

Make sure to snap an Instagram trophy at the southernmost point in the USA with the iconic striped buoy as your backdrop. Then make your way to Higgs Beach with its piers, parks, forts, and waterfront, or to locals’ favorite Fort Zachary Taylor Historic State Park, lovingly referred to by the LGBTQ community as Fort Liz Taylor Beach!

Get Up in the Air and Out on the Water: Take to the air in a Fly Key West helicopter and see the islands from on high. But also look down deep into the surrounding waters to spot the Keys’ famous sea life. Then, take a sunset sail on General Patton’s What & If Schooner which was built in 1939. This 80-foot sailing vessel is the epitome of seafaring beauty. Bring up to 28 of your friends on board. Make these excursions part of an April visit when Key West hosts the Conch Republic Days or part of an October visit and that month’s Royal Coronation Ball.

Dive Deep on Duval Street: All we have to say here is that you’ve never experienced a bar crawl quite like the ultimatebar crawl on Duval Street. Start at Sloppy Joe’s and keep going from there to countless other watering holes and live music venues. Just avoid becoming a Sloppy Joe!

Where to Eat:

While your bar crawl is going to scratch your boozy itch, do make sure you tuck into some of Key West’s favorite eateries. 

Latitudes: Accessible only by a short boat ride, this fine dining restaurant is famed for its surf, while delivering exceptional turf. Also, there’s nothing like dining looking out over the ocean.

Blue Heaven: By contrast to Latitudes, this is the spot where a cat or rooster might stroll under the table on which you’ll be served a fusion of classic cuisine with Caribbean spices and Key West flavors. Do not miss out on the key lime pie here.

El Siboney: With Cuba in the not-so-distant distance, why not indulge in Cuban staples of ropa vieja and picadillowashed down with exceptional sangria?!

Glazed Donuts: While most of the gay visitors to Key West will keep their sugary treats in liquid form, this beloved spot is a must not miss! Its name pretty much says all you need to know.

Reveling down Duval. Sunning in your birthday suit. Communing with nature. Bonding with loved ones. Meeting new loved ones. Simply being oneself with One Human Family. This is why Key West beckons and always welcomes back.