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The Must-See Attractions of… Key West

By Susan & Simon Veness

While the Sunshine State’s beaches and theme parks are the prime draws for the majority, Florida still boasts superb city experiences that are equally compelling. This series of blogs looks at the fabulous array of attractions that await in the state’s many urban destinations.

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Ernest Hemingway knew a thing or two about fun places to visit. Which is probably why he made Key West his home for almost all of the 1930s. This southernmost outpost of the continental USA is simply a full-on party town.

That’s not to say it doesn’t have more strings to its bow than bars and cafes – much more, in fact – but the basic atmosphere of Key West is laid back, informal, and it enjoys a drink or two.

Hemingway himself was quite the carouser, and his favourite haunts included Sloppy Joe’s, Captain Tony’s Saloon and Blue Heaven (the latter of which used to be a saloon), and you can still get the full flavour of these authentic bars today.

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In fact, one-and-a-quarter-mile Duval Street – which is Key West’s answer to Bourbon Street in New Orleans – is the epi-centre for the nightly fun and frolics that typically take over as the sun goes down, along with Mallory Square, which stages the signature Sunset Celebration each evening.

This is where you will find Sloppy Joe’s, and most of the other 50 or so bars that provide much of the city’s essential nightlife, including Sunset Pier (which is exactly as the name suggests!) and The Rum Bar (ditto).

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Getting Around Key West

While the original Old Town part of Key West (dating back to 1886) is eminently walkable, the best way to see most of the island is by the two all-day excursion tours that run from Mallory Square around the main historic district, stopping at various points, like a bus service, to allow passengers to hop on and off for the key sights.

Take your pick from the Conch Train Tour and the Old Town Trolley, with an all-day ticket for around $30/person that allows passengers to board and disembark as often as they like, while enjoying the constant narration of the city’s history and landmarks. You’ll get the full Key West overview and the lay of the land so you can return to your favourite parts later.

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Key West was still an island until 1912, when the Overseas Railroad arrived at the new Flagler Station. The Railroad finally linked all the islands of the Keys, until it was partly destroyed in the great hurricane of 1935 and replaced with roads and new bridges.

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Key West’s Museums

As you’d expect with a destination rich in the heritage of pirates, shipwrecks, Cuba, the railroad and its unique geology, there are a good number of museums that will provide the back-story of the island and its history over 200-plus years.

Learn about one of the largest treasure finds in history at the Mel Fisher Maritime Museum; pirates and more at the Shipwreck Museum; the Overseas Railroad at Flagler Station & Historeum; the city’s unique architecture at the Audubon House & Garden; maritime heritage at Key West Lighthouse & Keeper’s Museum; the former working holiday home of President Truman at the Little White House; and, of course, the Hemingway Home & Museum.

Be sure to take in two key landmarks, too. The Southernmost Point is the big selfie photo op, with a huge buoy depicting the exact geographical location of the all-important marker denoting the most southerly point of the continental US. Then there’s Fort Zachary Taylor Historic State Park, with its popular beach, picnic areas and walking trails.

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Key West Activities

If there’s one thing that Key West was built on, it is fishing. Inshore fishing, deep-sea fishing, fishing off the pier, fishing on the beach. It’s a fishing kind of place (as avid fisherman Hemingway would also attest). Florida as a whole is an epic place to go fishing, and the Keys represent the crème de la crème of its options. In Key West, it goes all the way up to 11.

There are more than 100 fishing charters and boat tours you can take here, and every one will provide that quintessential Keys experience, while also affording the chance to catch your dinner, as several hotels and restaurants will happily cook your catch for you!

But that’s far from all the outdoor activities here. You can take a dolphin-watch cruise, go snorkelling, diving or kayaking, and even try sky-diving from Sugar Loaf Shores Airport, “America’s most scenic drop-zone.” This is also a good place to hire a bike and go cycling, or take a sunset cruise.

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Great Dining, Too!

As a final thought on what Key West does well, this is definitely the place for a memorable dining experience. It should go without saying that local seafood will be a plentiful and must-try option, especially for yellowtail snapper, grouper and hogfish, as well as the Keys’ signature dish, conch, a large marine mollusk.

Upscale restaurants are also on the menu here, too. Look for swish Latitudes (part of the gorgeous Sunset Key Cottages resort – reservations essential), tapas-style Santiago’s Bodega, Ocean Grill & Bar, the laid-back Blue Heaven, inventive Seven Fish, stylish Café Marquesa and the lively Smokin’ Tuna Saloon.

And that’s Key West in all its glory. There is nowhere like it in Florida, and its uber-cool ‘Flori-bbean’ character is simply something you have to sample at least once in life. Visit, enjoy and discover that Hemingway vibe!

Susan & Simon Veness are the UK’s leading experts on Florida, having written about it for more than 25 years and sold more than half a million copies of their books about Orlando, Disney and the Sunshine State.

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