Once a rip-roaring buccaneers’ town, the preserve of pirates and wreckers, Key West is now the quirky, tropical heart of the Florida Keys. The island’s boisterous history, free-spirited outlook and unique “Floribbean” vibe prove powerful draws for everyone from artists to eccentrics, but there are plenty more compelling reasons to visit – here are seven of the best.

1. For the picture-perfect architecture

Key West is closer to Cuba than Miami, and the result is an unusual “Floribbean” feel. Cycle the Old Town and you’ll come across pastel-coloured homes behind white picket fences, their porches replete with rocking chairs and lined with gingerbread trim – you can imagine drinking iced tea here in the balmy heat.

Press on and you may encounter one of the mansions, looming structures with louvered shutters and soaring turrets, now home to plenty of ghosts (or so it’s claimed). Entering the brightly painted Bahama Village, the tin-roofed conch houses – many of which are former cigar factories – were built by Bahamian settlers and have an authentic Caribbean feel.

Bahama Village, Key West, FloridaImage by barbdean on Flickr (CC BY-NC-ND 2.0)

2. For the plunderers and polydactyls

The waters surrounding Key West were riddled with pirates in the early nineteenth century. This, along with strong currents and hazardous reefs, paved the way for a booming wrecking industry, with sailors racing to sinking ships to rescue the cargo.

By the 1850s, Key West was the wealthiest city in the USA. Various illustrious snowbirds settled here, including writer Ernest Hemingway and President Harry Truman. Today, you don’t have to look far for reminders of the past: you’ll find tales of shipwrecks and treasure-hunters in the museums, as well as around 50 six-toed descendants of Hemingway’s cat in his Spanish colonial home.

3. For the eccentric side of the Keys

A mob of chickens, descendants of Cuban fighting roosters, scratch in the dust of Duval Street, skirting a cross-legged street performer dressed as Spiderman, strumming a sitar. Throngs of low-rider bicycles appear as the sun descends, coated wheel to wheel with gaudy neon lights, while locals pour into a bar bedecked with an extraordinary collection of donated bras. And down in the cemetery, a tombstone has an unusual message: “I told you I was sick”.

Key West has always attracted its fair share of eccentrics, its tropical climate and southernmost location drawing outcasts, marauders and oddballs. But it’s this weirdness that most endears it: as the motto says, this is “one human family” and anything goes.

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4. To visit the Conch Republic

You’ll often hear Key West referred to as the “Conch Republic”, and the story behind how it got this nickname sheds light on the city’s sense of humour. In 1982, following a row with US border patrol over a roadblock, Key West jokingly seceded from the US and declared war.

The mayor then swiftly surrendered – though not before demanding a billion dollars in foreign aid. While Washington never officially responded, the offending roadblock was shortly lifted and Key West’s stunt succeeded. The Conch Republic Independence Celebration is now marked annually in April, and you’ll regularly see the micronation’s blue flags flying.

5. To celebrate… everything

Locals, known as “conchs” after the sea snails eaten here, seem to find a reason to celebrate almost anything in their typical quirky style. Fantasy Fest every October sees ten days of fancy-dress parades, pet masquerades and unfettered oddness (previous themes include “Habitat for Insanity” and “A-Conch-Alypse”).

On New Year’s Eve locals forgo the usual ball drop in favour of other traditions, like lowering a drag queen from a balcony in a gigantic high-heeled shoe. The most famous is the nightly Sunset Celebration, when crowds gather beside the ocean in Mallory Square for two hours of street performances and dazzlingly orange vistas.

19074785 - key west, fl - circa 2012 view slopppy joe

6. For drinks on Duval

The nightlife in Key West is raucous yet laidback. Many of the best places are centred around Duval Street, where you’ll find a clutch of noisy dive bars hosting everyone from ageing rockers to frat boys.

Try the Green Parrot for live music, where locals throw shapes until the early hours. Sloppy Joe’s is another popular spot, but despite what you may hear its original location (now Captain Tony’s Saloon) was the one frequented by Ernest Hemingway.

7. For the best Key Lime Pie

No one comes to Key West without trying several slices of Key Lime Pie – it was invented here. This tangy dessert – a sort of light, refreshing cheesecake – is made with limes grown locally and comes in lots of different varieties.

Blue Heaven offers slices topped with colossal clouds of meringue in a tropical yard filled with free-roaming chickens; Kermit’s has a frozen variety, served on a stick with a thick chocolate coating; while the pies at Key West Key Lime Pie Co. have a sweet graham cracker crust. Many local outlets claim to have the best recipe, and discussions on the subject can get rather heated.

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Georgia flew to Fort Lauderdale-Hollywood International Airport with Norwegian. She stayed at Playa Largo Resort & Spa in Key Largo, The Marker in Key West and Hawks Cay Resort in Duck Key. For more information on the Florida Keys and Key West, visit www.fla-keys.co.uk.