Key West, Florida.
Key West, the southernmost point in the United States (they like to tell you that. They like to tell you that quite a lot), is one of those strange little seaside places that seems made up. It’s one of those little American towns that doesn’t actually feel like America at all. Like it might decide not to be America any time soon and become part of another country. Maybe Cuba, which is only 90 miles in that direction anyway.
We’ve driven down from Miami in our fancy little Camaro convertible courtesy of Hertz and even though it’s often called one of the top road trips in all the Americas, truth be told, it can get a bit samey, even across those amazing, miles-long bridges. But then we arrive at The Marker, a brand-new-but-you’d-never-know-it resort-type hotel right down by the Waterfront (be careful which resorts you go to in Key West, by the way: they can get very generic if you stray too far from the town centre).
The Marker is all white clapboards and palms throwing dramatic shadows with big rooms that look right onto the waterfront, a funny little dock area with bars serving deep-fried seafood and stalls selling ‘Ray Bans’ for just $7. Two pools – one child-free where they’ll give you complimentary scuba diving lessons – and a pool bar/restaurant area so you only have to negotiate the chickens and the iguanas to get from your sunbed to lunch and cocktails. There’s strangely not much in the way of beach around these parts so you need somewhere with a good pool.
Just outside your door at The Marker is a town of little streets of white houses overgrown with palm trees and flowering bushes and maybe an old-fashioned bathtub repurposed as a fish tank out front and some cats sitting on rocking chairs on a stoop, the odd American flag, some fairy lights that someone once put up for Christmas and liked so much they never took them back down again and a little art deco theatre with a neon sign and a flashing poster announcing that gay film director John Waters is coming to do something, sometime just along from bars that have someone singing in them, even if it is sometimes to an empty room.
New Orleans is a bit like this. There’s a lawlessness to the place. They’ll even allow you to drink in the streets, which is very not-America.
Traditionally a resort for older gay men, the place does have a bit of a racy side to it if you know where to look. Explore the huge rambling premises thoroughly and you’ll find pools and Jacuzzis and decks to relax on. And there’s also a whole culture of clothing-optional carryings on in Key West. Island House is a clothing-optional resort, where you can stay or get a day pass to use the facilities and where you’ll find that clothing optional is just the start of what goes on. You can even go on men-only clothing-optional cruises. We love the sight of a penis as much as the next person, but this felt strange to us and we sort of preferred Danger Charters’ wine-tasting cruise where cheeky beardy sea dogs took us out on a sailboat at sunset and plied us with so much wine we had to throw some of it over the side. And that’s not like us at all.
As far as activities go, a lot of it is sea-facing, even in the absence of a nice beach. Jet skis, snorkeling (well, they have the only coral reef in America and water so clear and turquoise you’d be silly not to), parasailing, paddle-boarding… though there are more cerebral ways to spend your time if you don’t want your hair to frizz out.
Ernest Hemingway used to live here, so you can visit his rambling house and tickle the cats with six toes that he bred. And Harry S. Truman’s Little White House is worth a shot if you like your American history. It was also home to Tennessee Williams, which explains the museum and why the best little brunch spot in town is called Hot Tin Roof.
And if you want a Sunday which is gay but where no one is grinding their downstairs regions into your face, head to La Ti Da, an LGBTQ-run restaurant with a pool and a drag bar attached for a fairly high-class brunch. Yes, those things can co-exist and co-exist quite nicely in Key West. Just keep your eye out for those damn chickens.