Key West

Key Information – A very gay week in Key West

Key West is weird. Good weird, but weird. It’s a palm-tree covered, iguana-strewn island, but every inch of Key West is commercialised to within an inch of its four-square-mile life. It may be at the extreme end of the continental US, but, wouldn’t you know it, it’s also at the end of an enormous freeway. You’ll get guys from Havana popping up on your dating app (yes, really) but you’re never more than fifty feet from a corndog. None of this is necessarily bad (except, perhaps, for the environment) but if you’re looking for an unspoilt island paradise then I’m afraid you’ll have to look again. Oh, that’s me in the hammock.

On the Way

We drove from Miami. A mere step, in American terms, but quite an undertaking for little European me. It’s certainly scenic; the Overseas Highway endlessly snakes over and between the Florida Keys. There are some incredible views of distant and mysterious islands and a section called the Seven Mile Bridge, where a dizzying drive gives you a bleak but beautiful vista of the remains of the highway’s decaying predecessor. That’s all very exciting, although there’s also a lot of concrete. Concrete, fast food joints and a surprising array of billboards promoting a mysterious sandal factory outlet store which you never actually get to.


The Overseas Highway. Get used to the view.



As we turned off the freeway our first view of Key West comprised a petrol station, more concrete and a cock. Well, a cockerel, to be precise. Key West is absolutely covered in feral chickens. We almost ran over one of the petrol station forecourt. To my mind that’s no safe place for a cock. It turns out you have to drive through the industrial bit of the island until you get to its historic core. I decided to explore a bit whilst the Norwegian Boyfriend returned our Mustang to the car hire place at the airport (I say airport, it’s about the size of a sexual health clinic).

Save on brunch and collect your own eggs!


I soaked up the sun and balmy breeze. The Key West Historic District is unique and beautiful – a delightful mix of palm trees, gingerbread houses with immaculately-kept gardens and drunk American tourists. Our guest house, Alexander’s, was on Fleming Street, a long, straight road of serious real estate. I never tired of walking up and down it (which you have to in order to reach Duval Street, Key West’s throbbing heart), nosing in windows and dreaming of a colonial revival holiday home. It transpired that almost all Key West’s gay accommodations are on or around Fleming Street, including Island House and Equator (clothing optional gay-only resorts) both of which looked snazzy but not a patch on Alexander’s, which is by far the most premium gay (but straight-friendly) option in the historic district. It was so welcoming that we acquired a cohort of New Gay Friends after the first night, some of whom paid for a day pass to get into Island House to join in the naked pool frolics. Apparently it has a poolside café, spa treatments and other, let’s say, less salubrious amenities. They certainly looked very tired when they came back.

Happy hour at Alexander’s. The drinks were free and therefore we were happy.


Key West is not known for its beaches. There’s a reason for this. They’re not very good. We tried Higgs Beach first – it’s in a car park, there’s a restaurant that smells of bleach and some signs warning you that you’re about to be killed by jellyfish. The beach at Fort Zachary Taylor is rather prettier and lower on deadly marine threats, or at least if they’re there nobody tells you about it. If, despite my advice, you find yourself desperate for the beach don’t try to walk to Fort Zachary Taylor – it may look like a hop, skip and a jump but it’s a total hike through a naval base and a building site. A little Top Tip! is that you can get a cab to take you through the barrier and right to the beach.

Rainy Days and Excursions

If you feel the need for some culture (or if it rains) there’s Ernest Hemingway’s House and Truman’s Little White House. Expensive and commercialised, but worth a trip unless you want to go shopping, and I wouldn’t, unless you think a t-shirt saying ‘I’m so gay I shit rainbows’ is an appropriate souvenir for your frail aunty. There are many excursions on offer from Key West too, including a trip to the Dry Tortugas national park (didn’t look that exciting on the posters, but very remote) and various trips to the Everglades if you like being gnawed by reptiles. The Norwegian Boyfriend and his sister went on a snorkelling trip (I don’t snorkel after a near-drowning in Gran Canaria) and came back trousered on free beer and said they’d seen a shark (doubtful).

Food and Drink

We couldn’t wait to see what the nightlife had to offer. In Key West, there’s entertainment (having a nice time) and then there’s entertainment (looking at drunk middle-aged Americans on holiday). The main tourist area is on and around Duval Street. On our first night one of our New Gay Friends looked up from his Manhattan and said ‘Honey, whatever you do, when you get to Duval turn left’. Of course we went right. If you turn left you’ll find pleasant restaurants, attractive architecture and all of Key West’s gay nightspots. If you turn right, you’ll find the Hard Rock Café and an establishment called Sloppy Joe’s, which is apparently famous but frankly I don’t care to know what it’s famous for, sloppy or not. You’ll also find Hank and Pammy from Pensacola and their five thousand morbidly obese friends. They’ve all had an awful lot of pina colada and, trust me, they’re not going to bed anytime soon. Have a look at my round-up of Key West’s gay bars here.

We adopted this lonely swan at Alexander’s. She’s called Melania.

Top or Bottom?

I can’t wait to go back to Key West, there’s nowhere else quite like it. It’s almost always warm, it’s friendly and fun, the architecture is beautiful, there are bars and restaurants aplenty (see my separate blog post on Key West food) and if you want to feel like you’re somewhere exotic, well, it certainly hits the spot. It is, however, expensive, commercialised and full of drunken middle-aged tourists. Prepare yourself for them, the tacky shops, the heat and the inevitable mosquitoes and I’m sure that you’ll have even more fun than I did.

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