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Is Key West worth visiting? One hundred per cent, yes!

Key West, the most southern city in the USA, is a blast. Right on the water, it's America's answer to Brighton, but sunnier and warmer!

April 25, 2023


Welcome to Key West, the southernmost city in the Unites States of America, and a complete joy to visit. Sally, Girl About Leeds, and I could have spent weeks just wandering its streets and soaking up the atmosphere when we visited the Florida Keys at the beginning of March, and we didn’t want to leave.

Before we arrived, people had told us Key West was a bit like Brighton. No offence to Brighton, but it’s a bit like Brighton, and then some! Like Brighton, it’s a really welcoming, friendly waterfront city with a fierce independent spirit, but unlike Brighton, it’s blessed with a sub-tropical climate, is heavily influenced by how close it is to Cuba, and you can spot dolphins, snappers and lobster in its surrounding shimmering blue sea waters.

Long known as one of America’s most LGBTQ-friendly cities, at the beginning of 2000 local artist J.T. Thompson started giving away One Human Family stickers. Now, more than one million stickers have been sent out worldwide and it’s become an international grassroots movement to unite all people and to guarantee everyone equal rights, dignity and respect. The city of Key West has even adopted ‘All people are equal members of One Human Family’ as its official inclusive motto. This philosophy sets the tone for what to expect on a visit to Key West – it’s liberal, anything goes, and it feels friendly and safe for everyone.

sunset on a waterfront in Key West

Why is Key West so special?

A quick potted history of Key West, plus a sense of its location, helps understand how it’s become this inclusive, liberal outpost in a state that more often votes red than blue (if you’re not interested in the history, skip this part!).

Lying about 150 miles south of the mainland of Florida, Key West is a remote spot, and when it was founded in 1822, it was particularly remote. People weren’t really settling in southern Florida, Miami wasn’t even a speck of a hamlet, and it was hot and inhospitable.

Key West was just a barren rock with about 2,000 pirates calling it home, yet by 1851 it was the richest town in America with 200 of the country’s then 400 millionaires living there. Why? Because it’s got the deepest sea harbour in the States and is on the Gulf Stream from South America to America’s north east and Europe, and its founders made a fortune from salvaging shipwrecks on this very popular trading route. Ships fully loaded with gold and silver from South and Central America headed for Europe and would have to pass through the treacherous reefs. Inevitably there were many shipwrecks – some claim as many as one a week – and the first person to slap the side of a sinking ship could claim up to half the fortune on board.

From these rebellious beginnings, Key West found its fortune, and attracted migrants from both the nearby Bahamas and Cuba, bringing with them their own cultures and traditions whose influence remain today. It’s also in such a strategically important location that the US Navy has had a base here since 1823, but it wasn’t always on the up and the city declared bankruptcy twice, first in 1934 and again in 1975.

It was around the time of its first bankruptcy that the city began to attract influential cultural figures – Ernest Hemingway moved there in 1931, given a house by the city in the hope he’d attract other starry Hollywood friends, but then a huge hurricane came through in 1935 and destroyed the road bridge, plus the Great Depression lingered longer than expected, so that didn’t really happen.

In 1941, both Tennessee Williams and Leonard Bernstein made the move to Key West, as they’d heard that it was an easy live-and-let-live sanctuary, and their presence attracted other gay artists, notables and illuminati to visit, and stay.

The fact it was so difficult to reach Key West only added to its appeal and by the 1970s it was established as one of the world’s truly accepting come-as-you-are LGBTQ-friendly cities. It has prospered ever since, and became a haven for HIV positive people in the 1980s – there’s a memorial to the AIDS pandemic at the entrance to White Street Pier.

In 2018 Teri Johnston became mayor. She’s lived in Key West with her wife for more than 20 years and said when she was elected, “Labels work fine for clothes down here in Key West, not so much for people.” ‘One Human Family’ has become the prevailing spirit and it’s serving this little island and city very well.

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What are the highlights of Key West?

Okay, that was a bit longer than a potted history, but there’s a lot going on in this little city at the southernmost tip of America. If you’re visiting, and would like to learn more, I’d recommend joining the Key Lime Bike Tour around the city – our guide, James, gave a brilliantly entertaining account of the past 200 years, where most of the above is taken from, and seeing the city by bike meant we easily covered a lot of ground.

We arrived in Key West as the sun was setting – you get good sunsets in the Keys – and headed straight for dinner at La Te Da on Duval Street, the centre of Key West’s nightlife. La Te Da is a chic boutique hotel set around a courtyard swimming pool, with an open-air restaurant and a weekly cabaret show from Key West’s best drag artiste, Randy Roberts. A couple of cocktails over a delicious dinner and we were just in time to catch his show.

A stellar impersonator, Randy’s Cher was uncanny and Bette Middler was a knock-out. The intimate theatre means he can walk among the audience, flirting, teasing and cajoling as he pleases. Over a drink with him after the show, Randy described how he finds the show to be like a game of tennis – he’ll hit the conversational ball into the audience, then enjoys playing a game with what they hit back.

Randy takes us on a tour of downtown Key West, pointing out the Gay Key West Visitors Centre, the jazz bars, his favourite restaurant Nine One Five and introducing us to a couple of drag queens who’d just finished their show at Aqua. We dip in and out of bars, stroll the balmy streets, and end the night belting out karaoke at Bobby’s Monkey Bar, utterly in love with Key West.

The next day we join a snorkelling and dolphin-spotting tour with Honest Eco, Key West’s first electric catamaran tour that leaves from the Historic Seaport marina at the top end of town. Within 15 minutes of leaving the waterfront a couple of dolphins appear on the bow and dip and dive among the waves, then we moor above a sponge garden and snorkel only a few metres above the seabed. We spot lobsters hiding under boulders, sting rays disguised against the sand and even a moray eel, poking its head out from a little cave. Sally’s written more about Honest Eco on her activities blog linked below.
No visit to Key West would be complete without a visit to Half Shell Raw Bar. It’s in a prime position at the waterfront and serves every kind of fresh fish imaginable, as well as refreshing cocktails. It’s a great spot to sit and watch the world go bar, as fish swim in the water beneath the balcony, and sea gulls chance their luck with any leftovers.

Sally’s vegan so we ask around for recommendations to counter all the seafood, and Date & Thyme on Fleming St is mentioned again and again. It lives up to its billing – a whole food shop with an eat-in and takeaway menu of healthy, hearty salads and main courses, plus smoothies and fruit juices, we order an all-day veggie breakfast and a vegan burger (Sally’s ‘best ever’ – and that’s high praise from a vegan of 17 years) and eat them at one of the tables out the front as cockerels wander around us.

Cockerels? Yep, they roam free around Key West and have done ever since the Cubans first arrived in around 1860. The Cubans loved to cock fight, so brought cockerels over with them, but then when it was banned in the 1970s they threw them out into the street, and they’ve bred, and roamed free ever since (that’s another nugget of knowledge we learnt from James on the Key Lime Bike Tour).

Key West has had its fair share of famous residents. There’s a queue to visit Ernest Hemingway’s house, with its six-toed cats and the writer’s study as it would have been in the 1930s, and President Truman had his winter residence here on Front St, which you can also visit today. For a famous female face, head to Books and Books on Eaton St, owned and run by Judy Bloom. Often to be found serving behind the counter, the bookshop is one to easily lose yourself in for an hour or two, and is part of the Studios of Key West, a contemporary art centre and gallery.

Sunset is a big deal in Key West – it makes sense for a town that faces west and looks out to the ocean – so we had prime viewing on board an old-fashioned sailing schooner, one of the Wind and Wine sunset sails run by Danger Charters every late afternoon. Once we were out of the harbour the crew hoisted the sails and we tacked out to sea. As we criss-crossed the channels, the crew served up eight different wines to taste, along with canapés and nibbles, and the whole thing was perfectly timed for us to have uninterrupted views as the sun dipped beneath the horizon. If you’re not on a boat for sunset, head to Mallory Square at the water’s edge, where a daily party has evolved, complete with live music, entertainment and a big cheer as the sun goes down.

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Where to stay in Key West

In Key West, most of the hotels are either downtown or about 10 minutes drive from the old town, along N. Roosevelt Blyd. While it’s great to be in the heart of the action downtown, the hotels further out tend to have more space and we stayed at the three-star Havana Cabana hotel, a Cuban-styled bright and breezy place with a huge central pool (the largest in Key West) and cocktail bar, plus restaurant and parking. The hotel runs a shuttle bus to downtown every half hour (or it’s about $15 in an Uber), but it’s also great to just hang out by the pool – and the hotel serves free snacks and happy hour cocktails daily.

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April 25, 2023