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Florida Keys: The keys to happiness

Quirky, quaint and downright curious: on a self-drive tour of the Florida Keys, Pippa Jacks finds it impossible not to relax

Aerial shot of the Lower Keys.jpg
Aerial shot of the Lower Keys.jpg

If you must have the misfortune of getting lost in a dodgy part of downtown Miami, driving an unfamiliar car, then there are certain vehicles in which you have a better chance of blending in.


Unfortunately, a canary yellow convertible Mustang – with the top down and suitcases on the back seat – is not one of them, and my female friend and I are suddenly starting to feel very conspicuous.


It’s a wonder we even made it out of the airport: our Mustang is so huge and button-laden, it’s like driving a spaceship, and we had to do several practice laps of the car-park (much to the amusement of the Avis attendants).


With stress-levels sky high, I frantically scour a clutch of maps while we crawl around a dilapidated housing estate, trying to look as bad-ass as we possibly can.


After heading in the wrong direction more than half an hour, I realise I’ve mis-spelt “Islamorada” on the sat-nav, and we start heading in the right direction (south) on US Highway 1.


“Looks like you girls need a glass of champagne,” the receptionist at Cheeca Lodge sympathises, as we collapse into the chairs at the check-in desk, visibly traumatised. Never has a glass of bubbles been imbibed so quickly.


Happily, it is impossible to remain tense at Cheeca Lodge for long, and when we wake at 5.30am, throw open the balcony door, and lay eyes on the turquoise sea for the first time, we’re almost grateful for the jet lag that’s awoken us so early.


And we decide to iron out any last vestiges of tension with a smug sunrise yoga session in the gardens by the pool.

In good company
I’m not the first visitor to have come to Cheeca Lodge to relax: it first opened in 1946, and framed photos in the lobby display some of the hotel’s high-profile guests, including golfer Jack Nicklaus and former president George Bush Senior.


It’s one of the larger hotels in sleepy Islamorada, which is a collection of smaller islands, covering 20 of the archipelago’s 130 miles.


Fishing is one of the biggest attractions of the Florida Keys, with sailfish, marlin, tuna and kingfish coming close to the shore, while the “backcountry” flats teem with tarpon and bonefish.


Today I’m more interested in eating fish than catching it, and lunch upon crunchy, coconut-crusted shrimp at Islamorada Fish Company - a decidedly kitsch restaurant over the marina, with huge plastic marlin dangling from the rafters.


There are few natural sand beaches in the Keys (some hotels buy it in), but the fact the coral Keys offer such rich dive sites so close
to shore explains their appeal to divers and snorkellers.


You don’t need to be a diver to enjoy Islamorada’s History of Diving museum though: a funny little attraction that I have almost to myself, where I spend a fascinating two hours discovering how diving techniques and equipment have developed across the centuries.


Quirky attractions is something the Keys does very well, from tours of the old city morgue in Key West, to Jules’ Undersea Lodge on Key Largo, where guests can spend the night in an underwater capsule.


And the Keys have attracted more than their fair share of writers, hippies and odd-balls over the years, thanks to its relaxed Caribbean vibe (Key West is closer to Cuba than to Miami).


More recently, they’ve attracted Hollywood, with the drama Bloodline, starring Sissy Spacek and Kyle Chandler, being filmed at Islamorada’s exclusive resort, The Moorings.



The Moorings' Blue Charlotte House, the B&B from 'Bloodline'

Debating between The Moorings’ high-end restaurant Pierre’s, or its lower-key Morada Bay cafe next door, we plump for dining with our toes in the sand at the beach cafe. We enjoy our first of several mesmerising, pink-orange sunsets as we tuck into jerked grouper with coconut rice, and rather regret that we’re not in town for one of Morada Bay’s infamous, full moon parties.  

In the Limelight
All the sunshine and bare-foot dining seems to be doing the trick on the relaxation front, as we creak and groan remarkably less during our second beach-yoga session.


Before leaving Islamorada, we pop into Robbie’s Marina, which offers not only boat-hire and boat-trips, but the chance to feed gigantic, thrashing tarpon for a few dollars. We also discover undoubtedly the best thing that’s ever been put on a stick: a huge wedge of creamy, tangy, Key Lime pie, coated in thick chocolate.


Teetering on the edge of sugar-coma, we hit the road towards Key West. Now we’ve got used to the size and sensitivity of the Mustang, we are in love with it, and not just because it is incredibly easy to spot in the car park.


We whizz along Highway 1 and on to Seven Mile Bridge, passing mangroves, woods and infinite expanses of turquoise water.


With the roof down, sunglasses on, and American classics at full blast on the radio, it couldn’t be further removed from our first few hours with the car in Miami.


US Radio 1 interrupts our crooning to bring us the news, and we’re tickled to hear the biggest story of the day: “30-year-old Brandon Funkhouser has been arrested in the Keys accused of trespassing on a sailboat in Marathon City marina, and falling asleep on the couch, with a gift bag on his head”. 


The general sleepiness of the Keys – so ably demonstrated by Mr Funkhouser – means they haven’t changed much in years. Our hotel in Key West is The Marker, which opened at the end of last year, the first new hotel to open in Key West for two decades. It’s in the Historic Seaport in the west of the island, close to all the attractions such as Ernest Hemingway’s house and the nightly sunset festival in Mallory Square Dock.


It’s also close to the infamous Duval Street, where elegant restaurants and art galleries can be found alongside tacky T-shirt shops and singalong bars.


We devote equal time to each element, drinking cheap vodka from plastic glasses in Irish Kevin’s (tagline “I came, I drank, I can’t remember”) before moving on to The Other Side – a stylish cocktail bar, serving pricey but delicious concoctions such as The Relax Relapse and Hot Buttered Rum.  

Above board
Rum aficionados must also pay a visit to Key West’s First Legal Rum Distillery, where Paul Menta and his team have been producing “Chef Distilled” rum for almost two years. During the prohibition era the Florida Keys were a hot-bed for rum-running, and the state’s laws on distilling and retailing are still unusually strict.

Paul Menta, Florida Keys' First Legal Rum Distillery

Trained chef Paul brings a new level of culinary science to the process, including soaking the barrels in ocean-water instead of tap-water, and distilling it in six separate phases. Paul – who ironically is not a big drinker - makes the bold claim that his rum is so pure you’ll never get a hangover.


He’s not originally from the Keys but he’s come to love its idiosyncrasies.


“It has a really unique charm and community spirit,” he explains. “You can be hanging out with both a millionaire and a plumber at the same bar.”


He also notes a special sense of humour in the Keys. “Someone could start walking round with their pants on their head, and they might get arrested somewhere else, but here, we’re like, ‘Hey! It’s pants-on-head guy!’”


I suspect that guy would get on rather well Brandon Funkhouser.


Paul is proud that Chef Distilled was the only rum used at the recent Hemingway Look-A-Like competition (yes, that’s a real thing). And he’s also recently produced a special edition by submerging one barrel-ful inside the wreck of the Vandenberg.


This 160-metre long missile-tracking ship was purpose-sunk off the coast in 2009 to create Florida’s second largest artificial reef.


The uppermost parts of the wreck are as shallow as 12 metres, so I can see the looming silhouette as soon as we enter the water. It’s fascinating to think of the people and places the ship has seen, from being constructed in 1943, to carrying US troops in the First World War, and starring in the Jamie Lee Curtis movie Virus in 1999. Coral has now colonised the ship’s towers, hatches and cranes, and shoals of fish teem around us as we peer into the ship’s bridge and pose alongside the colossal satellite dish.


After one final evening of cocktails and dancing at Duval Street icon Sloppy Joe’s, we reluctantly pack up the Mustang and leave Key West the following morning.


As we drive out of town, a gentle rain quickly builds into a torrential downpour. It becomes so heavy we can’t see the car in front of us, and water several feet deep at the side of the road means driving is suddenly quite dangerous.


London-us would be shrieking and cursing by this point, but after four days here, it will take more than a flash-flood to rattle Keys-us. Instead, we pull into a roadside cafe, buy a slice of Key Lime pie, and chat to the locals while we wait for the worst of the rain to pass. Not so much taking it easy: taking it “Keysy”.


Book It: Caribtours has a seven-night package with three nights at Cheeca Lodge, three at The Marker, and one at the W South Beach, from £1,239pp including flights and car hire based on two sharing. Seven days’ car hire in a Group K car, such as a Ford Mustang convertible, costs from £233 in November in Miami with Avis, with unlimited mileage, LDW, ALI, tax, surcharge and airport fees. We were able to pay an extra $49 to return the vehicle to a South Beach depot (near our hotel) instead of at the airport. Virgin Atlantic flies daily from London Heathrow to Miami with prices from £427pp in economy. A second daily service will launch on October 2015.

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