Key West is a historical island town, party destination and retreat for the rich and famous.  

Do

Immortalised in film and literature, Key West is the southernmost point in the US and offers a taste of the Caribbean without leaving the USA. A naval base and, later, a party and holiday capital, Key West has always attracted celebrities looking for a private bolthole away from the maddening crowd. The town of Key West is centred on Duval Street, an occasionally raucous party strip in the centre of the old city. Visiting the bars here and fraternising with the other partiers can be fun but for something a little more grown-up in the area try The Porch, a purveyor of fine wine and craft beer favoured by locals and hidden from the Duval Street craziness by a lush tropical garden. Not as notable for its diving as sleepy Key Largo to the east, Key West nevertheless has some fabulous spots for snorkelling or scuba. Lost Reef Adventures (+1 305 296 9737) conducts regular tours aboard Dream, their custom-built dive boat, including to many nearby coral reefs and sunken wrecks. In addition to its party scene, Key West has a long tradition of playing host to writers and free spirits. Playwright Tennessee Williams, poet Wallace Stevens and, most famously, Ernest Hemingway have all called this island home. Hemingway’s beautiful house is now a museum, though the six-toed cats that haunt the grounds – descendants of Hemingway’s original – are arguably a bigger attraction than the historical artefacts.  

Eat and drink

The restaurant scene in Key West has a casual-dining emphasis, and the town is naturally famous for its seafood. For a reliable meal in the Duval Street district try Antonia’s (+1 305 294 6565). Set inside a charming Victorian weatherboard townhouse, the fresh pasta (seen hanging out the window to dry each morning) and local fish rarely disappoint. A hipper option is 2Cents (+1 305 414 8626). A bar and restaurant run by an expat from Portland, Oregon, it offers great cocktails accompanied by small and large plates with an emphasis on local produce and seasonality.  

Stay

There are many options for a great weekend away in Key West but if you want to pretend you’re Calvin Klein or one of Key West’s other celebrity habitués, then splash the cash and stay at Sunset Key Cottages (245 Front Street, Key West; +1 305 292 5300). Set on an island just off the shore of the town and reached by a ferry that runs 24 hours, the slight inconvenience is worth the luxury and isolation from the cruise ships and partiers in town. Including its own white-sand beach, stunning pool, excellent restaurant and all mod cons, this is a magical getaway from the getaway.  

Getting there

Drive 181kms across the ocean on the so-called Overseas Highway. This is one of the world’s most beautiful roads and a destination in itself. But remember: because you have to pass through various island communities, and slow down for wildlife, travel time for this relatively short trip still takes between about 3.5 to 4 hours. Alternatively you can fly (via regular airlines or sea plane) or, for a luxurious alternative, hire a yacht from one of the many charter companies in Miami.

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