Bar hopping in Key West

The Hedonist: What to see and where to be seen

Glass ceiling: Square One restaurant

Once home to Ernest Hemingway and Tennessee Williams, this two-by-four mile island at the tail end of the Florida Keys is made for pleasure seekers. I arrive at Key West's tiny airport and pick up a taxi to Sunset Key Island (001 305 292 5300; westinsunsetkeycottages.com) – a minuscule private island off the mainland that's sprinkled with mint-green cottages. I'm greeted by a porch with rocking chair, then inside, a yard-high bed. It all combines to make me feel as if I've stepped into the pages of a Ralph Lauren summer catalogue.

After unpacking, I head back to the main island to Duval Street. Despite its popularity among Florida University students and the LGBT crowd, the buzz of Key West's nightlife is a few notches below the all-night fist-pumping further north-east in Miami. I start with dinner at Square One (001 305 296 4300; squareonekeywest.com), an upscale eatery whose owner, Michael, greets guests with the enthusiasm of a long-time local. Michael clearly pays similar attention to the food because the specials and signature crab cakes are incredible.

Down the road, Nine One Five (001 305 296 0669; 915duval.com) is a charming restaurant owned by a British expatriate, Stuart Kemp, whose creative cuisine integrates some of the best of British with the fresh flavours of the Keys.

After dinner it's on to one of Key West's oldest bars, Afterdeck at Louie's Backyard (001 305 294 1061; louiesbackyard.com). Walking into Louie's feels like crashing a neighbourhood block party where everyone knows each other. Luckily, the drinks are strong and after a few Louie's Passions, I seem to have adopted a South Florida drawl – a sign it's time to move on.

I head to the most rambunctious bar on the island – Sloppy Joe's (001 305 294 5717; sloppyjoes.com). Another Key West institution known for pulling in a crowd of frat boys and blonde sorority girls, this is where the regrets of youth are made. I've only been in for a few seconds when the first tequila body-shot comes. The rest is history.

It's morning and my hangover needs nursing so I head over to Blue Heaven (001 305 296 8666; blueheavenkw.com) for a Bloody Mary and lobster omelette. No-nonsense waitresses dole out equal servings of attitude and coffee; and just about every face from last night is here.

Sufficiently stuffed, I jump on board the Conch Tour Train (001 888 916 8687; conch tourtrain.com) to see the island by day. Initially, this ride sounds like tourist-trap hell, but drinks are allowed on board. The tour takes in sights such as Harry S Truman's Little White House, Hemingway's home, Audubon House and the 1912 Flagler train station.

But the best part of being in the Keys is its location in the Gulf of Mexico, so I head out to sea on a private boat with Dolphin Safari Charters (001 305 797 5491; safaricharters.com) to do a bit of snorkelling and dolphin-spotting. I crack open a couple of cold beers while dolphins swim by, as the sun gradually sets over the pale-blue waters.

As night falls, it's back to Duval Street for key lime pie at Kermit's Key Lime Pie Shoppe (001 800 376 0806; keylimeshop.com). The zingy pies work a treat, before another night of cocktails.

A Hedonist's Guide to ... (Hg2) is a luxury city guide series for the more decadent traveller. For more information , see hg2.com