When John first took his husband Michael, then his boyfriend, to Key West, it was a major turning point in their relationship.
“It was literally the first time I had ever gone on a trip like this with someone I was dating,” Michael recounted recently over a Zoom call. “I think I actually cried at the airport over our mimosas.”
“You cried when we checked into our room!” John chimed in.
Now, the pair has gone from frequent Florida visitors to full-time residents. After years of traveling from New York to Key West, John and Michael could no longer resist the pull of the popular LGBTQ travel destination. The pair hopped in their car in July and drove straight down to Key West, their new home.
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Sure they were trading skyscrapers and subway trains for palm trees and swimming pools, but the Conch Republic and the Big Apple might have more in common than some visitors realize.
“It’s like New York because there’s a very engaged community,” John said. “It’s like New York in that it’s fairly liberal, politically, in regard to social justice and especially the environment.”
Also like New York, Key West boasts tons of great dining. However, the idyllic climate means even more options for spreading out and enjoying a meal in the fresh air.
“That was part of our calculus in moving down here in the first place,” John confessed. “Outdoor dining is practical all year-round.”
It’s not difficult to find good food in Key West, but John and Michael were eager to dish on some of their favorites, including the adorable French bakery and bistro, La Grignote (French for “the snack”). Scrumptious French pastries are made on-site daily, while owners Joel and Babette’s dog greets customers wearing a signature “Don’t Feed Me” scarf. (More for us, we say.)
John and Michael frequently visit one of local cabaret legend Randy Roberts‘ favorite haunts: the beloved Point5, upstairs from another Duval Street staple, Nine One Five. Grab an open-air spot and enjoy gazing down at Duval while sampling one of Executive Chef Brendan Orr’s signature small bites. It’s the perfect spot to cap off a day of shopping along Duval, supporting the local business community, including the island’s longest-running, gay-owned and operated retail space, Graffitti.
There’s a lot more to do outdoors in Key West than just eat and shop.
The sunny weather and inviting water also make it an ideal location to try kayaking, snorkeling, jet skis or a private tour aboard the island’s famous clothing-optional boat, Blu Q.
It’s tough to resist, even if you’re not typically aquatically adventurous.
“I am a consummate Earth sign,” said Michael. “Even the concept of snorkeling or going out into open water in the ocean was initially terrifying.”
“You were a trooper though!” John reassured him.
Not all water sports are so action-packed. Key West’s LGBTQ nightlife soldiers on, with many bars and resorts taking advantage of their outdoor space to allow patrons to spread out. The famed all-male, clothing-optional resort, Island House, for example, has expanded its café seating poolside in lieu of lounge chairs. Or, the guys recommend grabbing a poolside drink in the large backyard at Bourbon Street.
Of course, whether you’re a resident or just visiting, there’s one signature Key West experience that’s always worth a stop: Sunset at Mallory Square. In fact, it was one of the things John was most excited to show Michael on that first trip years ago.
“I was excited for him to see all the artists and the street performers at sunset at Mallory Square,” John said. “It hits all the marks: Beautiful sunset, you can appreciate nature, the tropical climate and you’re surrounded by local performers doing their thing, hustling and making their living.”
“It’s definitely a thing we constantly go back to, because it’s sort of a benchmark for the things we love about this place,” Michael added. “I’m a working artist, so going into a town where it was immediately very quirky and supported local art and kind of supported weirdness in general and being their authentic selves, that for me was the draw, ultimately.”
