Why Key West?
Nowhere has made a virtue of being out on a limb like Key West. At the end of the Florida Keys island chain, and a four hour drive over spectacular bridges from Miami, it is not somewhere you stumble across accidentally.
Those that make it to Key West really want to be there, and this feeds an air of utterly compelling woozy eccentricity. You can never quite be sure whether the swaying man in a Hawaiian shirt and flip flops is a hobo or a billionaire letting it all hang loose.
Around this vibe of often surreal silliness is a heritage of shipwrecks, pirates and Ernest Hemingway debauchery. If Disney repositioned itself for adults, Key West is possibly what it’d come up with.
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BOOK YOUR OWN ADVENTUREThe following sites are usually my first port of call when booking a trip - so I recommend them as somewhere to start when booking your own holiday.
HOTELS: Hotels.com (£) or Agoda (£)
FLIGHTS: Skyscanner (£) Kayak or Roundtheworldflights.com
CAR HIRE: Car Rentals (£)
GUIDE BOOKS: Amazon (£)
TOURS AND ACTIVITIES: Viator (£)
A comfortable bed
Newly-opened next to the Historic Seaport, The Marker (www.themarkerkeywest.com; 00 1 305 501 5193) gets the local feel right with Keys-made products in the mini bar and books about old Key West on the shelf. But there’s an understated air of luxury to go with three pools and a look that balances crisp modernity with tropical boldness. King rooms cost from $230.
The Truman Hotel (trumanhotel.com; 00 1 305 296 6700) is a mazy network of old wooden buildings, with a gorgeous palm-fringed and pool-focused central courtyard. Bright, bold rooms with zebra print rugs are a great fit for the destination. Doubles cost from $201.
The Avalon Bed and Breakfast (www.avalonbnb.com; 00 1 305 294 8233) occupies a swoony late 19th century building, and free fruit and brownies give a homeliness that go along with the evocatively old-fashioned furniture and canopy-netted beds. Queen rooms cost from $168.
Find your feet
Key West’s walkability and the sheer number of attractions crammed into a relatively small area are keys ingredient in the magic formula. Start at the Historic Seaport and you don’t have to walk too long until you’re at the Mel Fisher Museum (www.melfisherorg; 00 1 305 294 2633), which showcases booty salvaged from shipwrecks.
Carry on, and you’ll hit the Hemingway Home (www.hemingwayhome.com; 00 1 305 294 1136), where Ernest Hemingway lived for the bulk of the 1930s. Now a museum, it is overrun by the descendants of the six-toed cats he kept as pets.
Inside the Truman Annex is the Little White House (www.trumanlittlewhitehouse.com; 00 1 305 294 9911), which US President Harry Truman used for working holidays while US president. The tours inside provide a fascinating insight into the man, his idiosyncrasies and the era.
At sunset, switch back round towards Mallory Square to see the sky turn pink and legions of street entertainers perform.
Meet the locals
Part of what makes Key West so enjoyable is that it is not a beach destination, which instantly puts off anyone who would come for a sun lounger-style holiday. The beaches are pretty ropey, all told, but locals know you have to pay to access the best on the island. It’s at the southern end of the Fort Zachary Taylor State Park (www.floridastateparks.org/park/Fort-Taylor), and the $2 (Dh7) pedestrian entrance fee is well worth it on a hot day.
Book a table
Nine One Five (www.915duval.com; 00 1 305 296 0669) is about as buttoned up and upscale as Key West gets, and there’s an internationalist menu (albeit with local seafood leanings). Try the Moroccan vegetable ragout with preserved lemon yoghurt and saffron cous cous for $24.
Far enough away from the main drag that you really need someone to tell you it’s there, El Siboney (www.elsiboneyrestaurant.com; 00 1 305 296 4184) is such a local favourite that there are frequently queues outside. At this no-nonsense Cuban joint, trad dishes such as the $11.50 ropa vieja (stewed, shredded beef) and massive portions are what it’s all about.
The further south you walk along main drag Duval Street, the classier it gets. There are some rather interesting galleries and independent shops in the mix too. The Green Pineapple at number 1130 has yoga-matted soft floors, hippy-style basket bags and a distinctly boho line in fashion. The Island Arts Co-op next door sells locally made souvenirs – everything from painted ceramic tiles to carved wooden pelicans. Cocktails at 808 is great for colourful, hand-painted glassware.
What to avoid
The local treat is key lime pie, which combines sweetness and tartness to glorious effect. The amateur mistake is to expect it to be green. Key limes are yellow, so avoid anywhere selling green ones – it’s all food dye.
Key West may be the last of the Keys, but there are more tiny specks of land further into the Gulf of www.drytortugas.com; 00 1 305 294 7009) fast ferry, and have a proper desert island feel. Beaches and snorkelling are the initial attractions, but Fort Jefferson on Garden Key is what stays in the memory. The monstrous, hexagonal 19th century fortress is the largest masonry structure in the Americas. Day trips cost $170.. The Dry Tortugas are two hours, fifteen minutes away on the Yankee Freedom III (
This guide was researched in January 2015 and originally published in The National.
All content copyright David Whitley.