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

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.