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A Postcard From Key West

By Rebecca Miles

This is a feature from Issue 19 of Charitable Traveller. 

Head south as far as you can down the eastern coast of America and at the end of US Route 1 is the surprising city of Key West. It’s the largest city of the Florida Keys, the long, thin archipelago that stretches south of Miami and splits the Gulf of Mexico from the Atlantic Ocean.
But why surprising? Because this city, as the crow flies is closer to Havana in Cuba than Miami on the Florida mainland and is heavily influenced not just by that island, but the rest of the Caribbean too. It’s a welcoming inclusive enclave – very LGBTQ+ friendly – and surrounded by coral reefs. The sea plays a huge part in both its history and its present-day appeal, with lots of activities to get out and about on the water. 

To do that, I join a snorkelling and dolphin-spotting tour with Honest Eco, which runs Key West’s first electric catamaran. Within 15 minutes of leaving the Historic Seaport marina, a couple of dolphins appear on the bow then as a sponge garden we snorkel above lobsters hiding under boulders, sting rays disguised against the sand and even a moray eel, poking its head out from a little cave. 

Check into the Havana Cabana Hotel - it's got the largest pool in Key West and is a 10-minute shuttle from the old town.

Fresh fish is a big deal on the menus here, and the Half Shell Raw Bar on the waterfront serves some of the best.

Back on land, I take a cycling tour of the small city with Key Lime Bike Tours, where our tour guide, James, gives a thoroughly entertaining potted history of the past 200 years, including cameos from Ernest Hemingway, President Truman, the US Navy, and Cuban cockerels.
Key West is compact, so it’s easy to walk or cycle around and its streets are lined with great places to eat and drink. I find plenty of independent businesses – highlights include Books & Booka, owned by the author Judy Blume, dinner and Randy Roberts’ drag show at La Te DA, the centre of Key West’s nightlight, and inventive vegan food at Date & Thyme on Fleming Street. Spend a few days here and it’s clear to see why such a colourful cast of characters have made the journey to Key West over the years.

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This is a feature from Issue 19 of Charitable Traveller.