The insider’s guide to Key West – from the gay men who love it so much they moved there

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Key West Lighthouse
Key West Lighthouse

Key West offers one of the most unique vacation spots anywhere in the U.S.

Located at the tip of the Florida Keys, Key West boasts year-round sunshine, crystal clear waters, and a rich, vibrant history.

But don’t just take our word for it: We caught up with two locals who were so blown away by the place during a vacation, they decided to make it their home.

Christopher Massicotte

Christopher Massicotte (right) and partner, Eric
Christopher Massicotte (right) and partner, Eric Ault, on a recent Key West fishing trip (Photo: Supplied)

Christopher is a political strategist who lives in the Casa Marina neighborhood of Key West with his fiancé, Eric Ault, a flight attendant.

Where are you from originally?

I am originally from Massachusetts, went to college in Philadelphia, moved to Washington DC where I lived and worked in politics for 15 years, and then on to Key West. I came on vacation to escape Donald Trump’s inauguration in January of 2017. While there I woke up in the middle of the night and said to myself, “I’m not going back.”

I did the responsible thing and made arrangements to spend more time in Key West while still keeping my job, eventually selling my house in DC and moving here permanently in 2019. Every time I have moved it has been further south. Now that I live in the Southernmost City, I think I’ll stay.

I am currently engaged to my fiancé, whom I met just before the COVID lockdown. I was in Orlando for work and he was in Orlando on a layover. He’s a flight attendant. We met at the hotel and I invited him to come visit me in Key West. Lockdown happened and he never left. Eight months later, we were engaged!

What reactions do you hear from first-time visitors to Key West? 

Key West is visually stunning. When you fly in you see crystal blue oceans and a coral reef that appears to be teeming with life. Visitors expect a great bar scene and they are not disappointed. Bars are slowly recovering from COVID, but you can now walk down Duval Street and hear live music pouring into the street from various venues. We also have some fabulous restaurants serving all kinds of cuisine.

What many don’t expect is the rich history of Key West and the historic architecture. US President Harry Truman spent six months of his presidency in Key West and you can visit the “Truman Little White House.”

Several great authors dead and alive have called Key West home, including Ernest Hemingway, Elizabeth Bishop, Tennessee Williams, Shel Silverstein, and Judy Blume.

The arts are a big part of our culture in Key West. There are a lot of stores and galleries along Duval Street that celebrate Key West Culture, be sure to visit Tucker’s Provisions, Effusion Gallery, and Mel Fisher’s Treasures.

Ernest Hemingway's former home in Key West - now a museum
Ernest Hemingway’s former home in Key West – now a museum (Photo: David Hudson)

Why do you think people fall in love with Key West?

People fall in love with Key West because almost everyone who visits experiences some “Key West Magic.” This magic can come in the form of a rare green flash [a meteorological optical phenomenon] on a sailboat at sunset or spotting a manatee while kayaking in the mangroves.

The Key West magic can be meeting a celebrity at a local bar and chatting with them until the last call or a simple stroll through Old Town and taking in the sights and the history. Almost everyone experiences something special when they come to Key West, and that’s why they come back.

Kenny Chesney wrote a song about Key West. It’s called “Magic.” Almost everyone who moves to Key West from the mainland is escaping something. This place can heal your soul and make you a new person.

Key West offers a multitude of boating and other water activities (Photo: Florida Keys)

What’s a must-do Key West experience?

The one thing you must do in Key West when you’re here is get out on the water. It could be a simple wine and wind sunset sail on Danger Charters or you can hire a captain to take you out to the reef to snorkel, fish, and lay in the sun on a sandbar with not a single building in sight.

What are your favorite restaurants?

My favorite restaurants in Key West proper are Louie’s Backyard: the Afterdeck bar is on the water and having an after-dinner cocktail and chatting with the always friendly bartenders is great.

I also love Salute! On The Beach on Sundays where they usually have great live music. None of the seafood served at Salute had to ride on an airplane to get there, and the menu is full of delicious and (mostly) healthy options.

I also love the restaurant at the all-male gay resort, Island House, believe it or not. Island House is LGBTQ-owned and is consistently rated among the best gay resorts in the world. Their menu can accommodate any dietary needs and features fresh, local ingredients. You do not need to be staying there to visit the restaurant.

The Flaming Buoy, also LGBTQ owned, serves very inventive and delicious Key West island cuisine. Off the beaten path, El Siboney serves the most authentic Cuban food outside of Havana.

The Afterdeck Bar at Louie’s Backyard in Key West
The Afterdeck Bar at Louie’s Backyard (Photo: Louie’s Backyard)

Favorite bars?

For bars, I already mentioned The Afterdeck at Louie’s backyard. Bourbon Street Pub, live singers, and go-go boys perform every night and the drag shows at Aqua and 801 Bourbon are LGBTQ staples in Key West. General Horseplay has a bunch of really fun bar games, and they make some of the best craft cocktails I have tasted. For live music, I love the Schooner Wharf bar or Viva Saloon.

What beach should people visit and why?

I love going to Fort Zachary Taylor. It is a Florida State park so you will have to pay a fee to get in but it has the nicest beach and biking trails in Key West. Get there early on popular days as it quickly reaches capacity as they are restricting numbers due to COVID.

Jeffrey Smead

Jeffrey Smead (left) and husband James Braun at Fort Jefferson
Jeffrey Smead (left) and husband James Braun at Fort Jefferson (Photo: Supplied)

Jeffrey works in historic home renovation. He and his husband, James Braun, who works for a major beverage wholesaler, live in the Old Town district, “right on the historic Key West Cemetery.” They met in 2012 and married in 2017.

Where are you from originally?

I grew up in western Massachusetts. I moved to Key West after graduating college in Los Angeles in 2006. So I’ve been on the island for about 15 years. I met my husband here in 2012, very soon after he moved here from P’town. I was the Director of Marketing for the Island House Resort for 10 years, and as of last summer, I’m working full time on my/our third house renovation in Key West.

What reactions do you hear from first-time visitors to Key West?

People fall in love with Key West the moment they get here. Traveling here by plane really gives you a perspective of how small and remote the island is in relation to the mainland. And driving south via car on US1 Highway is like a vortex that transports you back in time. When you get to the end of the road, there’s this little crazy place called Key West. It’s magic. If you’ve ever thought you were an old soul, take that drive at sunset, and tell me how much you cried when it hit you. People write books about it.

Why do you think people fall in love with Key West?

Key West, whether because of its uniquely remote location, warm weather, or the locals, makes people feel liberated. You are here for an adventure on a quirky tropical island. You feel like you must be in a different country because you don’t recognize this island vibe from anywhere else in the United States.

That “lost but found” feeling is what keeps people coming back. This is the end of the road, and visitors chase that feeling of freedom each time they visit. I’ve seen a lot of grown men get teary-eyed when it comes time to go back home.

What’s a must-do Key West experience?

You cannot miss dedicating one full day to going to the Dry Tortugas National Park. It’s a remote island that is 70 miles offshore from Key West. You can book tickets to ride the catamaran, or you can invest a little more to be able to fly there on a six-person floating seaplane.

The Dry Tortugas is the most remote National Park in the country, and Fort Jefferson is the most remote Civil War Fort, set right on its own island with a private beach and even a moat surrounding the Fort.

You can snorkel for hours right from the shore, and enjoy one of the few places you cannot get cell phone service, no matter who is your phone carrier. Lunch is included on the catamaran, and they have a bar too! You can spend all day exploring the Fort itself, lounge on the beach, swim, snorkel, and even camp overnight.

General Horseplay (Photo: General Horseplay)

What about restaurants and bars?

Nine One Five: This place is such an incredible dining experience. High-end shareable plates, incredible handmade cocktails, and a funky jazz vibe that is not found anywhere else on Duval Street. I love the short ribs, the seafood hot pot, pistachio tacos, and the bacon-wrapped dates.

Latitudes: You have to make a reservation for the 5-minute ferry boat from Mallory square to Sunset Key Island, where Latitutes is the only restaurant, and one of the finest in Key West. I love this place for a beach lunch with toes in the sand, amazing Bellinis, and American fare that is both delicious and worth the experience of boating to the destination.

Seven Fish: Casual yet classy, this place has a fresh-caught curry Yellowtail Snapper entree that has been its best seller for eons.

For bars, try General Horseplay and 22&Co.

Dining at Island House in Key West
Dining at Island House (Photo: Island House)

What beach do recommend people visit and why?

Fort Zachary Taylor Beach is an easy 10-minute bike ride from anywhere in Old Town. If you go all the way down towards the jetty, that’s where most of “the gays” tend to run into each other. You can bring your own beverages, or there’s a snack bar with beers and seltzers, and a good choice of beach-friendly eats, too.

For the latest health and safety protocols in The Florida Keys, visit fla-keys.com/gaykeywest