Key West is the island at the very tip of the Florida Keys archipelago. As such, it’s the southernmost point of mainland USA. You’d be forgiven for picturing Disney World when you hear Florida, but Key West is almost 400 miles away geographically, and a million miles away philosophically.

You can fly into Fort Lauderdale Airport, direct from Gatwick Airport in London. From there it’s a four hour drive south, which may sound like a slog after a few hours on a plane, but it’s one of the most iconic and beautiful drives you’ll ever make, passing through the other Florida Keys.

Why Go?

Key West is, like the best things in life, a complex mix of contradictory elements. The architecture has a classic, Deep South feel to it, yet it’s a gloriously liberal town. Every corner is steeped in iconic Americana, and yet the influence of nearby Cuba also seemingly runs through everything.

The town reportedly attracts elderly US citizens, lovingly called ‘snow birds’ from colder, more northerly states in winter, yet the atmosphere remains youthful and joyous. Key West is a charming little puzzle, and one that’s easy to get lost in the rhythm of.

Hiring a personal water craft is one of the best, and most adrenaline packed ways to see Key West - Photo: Getty

Jet ski hire on Key West

Key West, an anglicised version of the Spanish Cayo Hueso which literally means Land of Bones, owes much of it’s success to early smugglers and salvagers, who’d rush out to sea to claim the bounty from sunken ships bringing riches back to Europe from South America. And it’s in the water where many modern day adventures can be had.

Key West is surrounded by the turquoise waters of the Gulf of Mexico and the Atlantic Ocean. While the relatively still waters of Key West don't lend them self to traditional surfing, it makes it a perfect place for Stand Up Paddleboarding.

There a more than a handful of places where you can hire a Stand Up board from, with some including guides who will take you into the mangroves in what will feel like true exploration. But for something a little different, Key West Paddle offer Night Boarding, where a SUP board is lit from beneath with waterproof LEDs, allowing you to see the sea creatures that only come out at night.

A paddleboarder enjoys the calm waters of key West - Photo: Getty

female paddleboarder enjoys the calm waters of key West

Similarly, windsurfing and kitesurfing are available to enjoy when the wind is strong enough, and kayaking provides an excellent option when it’s less gusty (which, if we’re being completely honest, it is most of the time).

If you’re looking for a little more horsepower, hiring a personal watercraft (or Jet Ski, to you and me) for a tour of the coast line is an adrenaline fueled way to spend a couple of hours. As ever, there are numerous places on Kew West to hire Jet Skis from, although we particularly enjoyed the tour given by the chaps at Barefoot Billy’s on the southern edge of the island, taking in most of the coast, and stopping mercifully short of the largest floating nudist colony in the world, just off Key West.

Where To Stay?

The Marker hotel in Key West is ideally situated

The Marker hotel in Key West

If you’re looking at enjoying a luxurious break in Key West, The Marker is an excellent hotel. It’s located on the north west if the island, which is a superb location as it’s only a short walk from all of the amenities and points of interest in Key West. Even the Markers most modestly priced rooms are large, spacious, and indulgently comfy.

If your budget is a little tighter, then Heron House offers cosy rooms in a classic wooden town house style. It’s located centrally in the town, so is no more than a short walk from the beaches, and museums on the island.

Where To Eat?

Not a lover of fish? The Stoned Crab in Key West will convert you - Photo: Stoned Crab

The Stoned Crab in Key West

Key lime pie is the signature dish of Key West, with just about every restaurant claiming to serve not just the best, but the definitive version of the desert. However, when you’re surrounded by so much ocean, it’s hard to resist the allure of fish.

Some of the best, not to mention freshest fish you’ll ever eat can be found at The Stoned Crab, just off Highway One on the north east of the island. Sitting right on the coast, it makes for a superb place to watch the sun set in the evenings while you’re tucking into your food. The atmosphere is relaxed, the portions are large, and the quality is really excellent.

If you’re looking for a more traditional restaurant feel to proceedings, Hot Tin Roof is an excellent option. It’s part of the Ocean Key hotel, but don’t be fooled into thinking this is like the dining hall at a motorway hotel near Grimsby. This opulent restaurant is sat next to Mallory Square - home of the Key West Sunset Celebration - so the views over the ocean are incredible. Again, fish dishes make up a large portion of the menu, but there are also plenty of meat and vegetarian options available.

Where To Drink?

The Green Parrot in Key West, a dive par favoured by the locals - Photo: James Renhard

The Green Parrot in Key West, a dive par favoured by the locals

Kew West is a real party town, and you’ll find no shortage of places to indulge in a mojito or five, especially on Duval Street - the Kew West equivalent of The Strip. However, no trip to Key West would be complete without a stop at Sloppy Joe’s. The favourite bar of Ernest Hemingway - a man who knew a thing or two about a drink - it’s a lively bar where live music plays, drinks flow, and locals and tourists alike dance with enthusiasm, if not always ability, until the early hours every night.

If that sounds a little too raucous, the bar favoured by the Key West locals is The Green Parrot. It’s what our American cousins would affectionately call a ‘dive bar’, packed with character and beer-stained history. The atmosphere is relaxed but enjoyable, and the locals are more than happy to stop for a chat with out-of-towners. In fact, if it wasn’t for the need to catch a flight back to the UK, We’d probably still be in the Green Parrot now.

What The Locals Say

"Key West has a renegade edge-of-the-continent appeal to it, blended with a lively seafaring vibe. And a place where people's professions can include treasure hunter, acrobat and poet is bound to attract plenty of adventurous spirits."

Carol Shaughnessy, who has lived in Key West as a resident writer and publicist for 35 years.

For further information on visiting Key West, check out the official website.