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US Route One, near Islamorada (Image: Getty Images)

The driver of the Conch Train proved to be a most illuminating guide to the vibrant and quirky town which is the last of the long line of islands of the Florida archipelago. 

A train full of tourists passing by his house would probably not have amused Ernest Hemingway, who lived here in the 1930s, but the islanders are immensely proud of the author who spent his time here writing, fishing for marlin and drinking (profusely). 

His house, built in the Spanish colonial style, is now a fascinating museum with a tour that ends on an inspiring note in the studio where he produced For Whom The Bell Tolls and The Snows Of Kilimanjaro. 

The house is home to 54 cats, which are descendants of Papa Hemingway’s polydactyl (six-toed) cat, Snow White, which was given to the author by a local fisherman. 

“Cats gave him a sense of peace when he was writing,” explains the house manager Jacqui Sands. 

Key West may be built on impenetrable rock but it did not deter Hemingway’s second wife Pauline, who was determined to have the island’s first swimming pool built in the garden – whatever the cost. 

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The pool was meant to be a surprise for Ernest, who was away covering the Spanish Civil War (and canoodling with the journalist Martha Gellhorn, who was to become his next wife) but on his return he was furious at the astronomical bill. 

You can still see, embedded in cement by the pool, a coin which Hemingway had tossed on the ground, ranting that Pauline had “spent his last cent”. 

No wonder he preferred to slip away for more rum at one of his favourite watering holes, Sloppy Joe’s, which is still doing a roaring trade, and was so named in the 1930s because the owner was taunted for running a “sloppy” place when the ice in his drinks kept melting in the heat. 

The bar holds the annual Hemingway lookalike contest, when around 100 men sporting beards compete to see who most resembles the grizzled author. 

Our road trip along US Highway 1 started in Miami, with two days at the Loews Hotel with the beach on one side and the city on the other. 

Joined by my wife and our 12-year-old daughter, we had planned a demanding itinerary to see as much as possible of the Keys, starting with a visit to the John Pennekamp Coral Reef State Park, where we clambered aboard a boat to snorkel among the mangrove swamps and reefs of what is billed as America’s “first undersea park”. 

Captain Darrell certainly did his best to ensure we enjoyed a marvellous two hours dipping underwater to see angelfish, parrot fish and the occasional (and harmless) nurse shark. 


Florida Keys, Grassy Key, Dolphin Research Center (Image: Stephen Saks Photography / Alamy)

That night we stayed in a simple room at the Amara Cay Hotel, the perfect place to relax with a supper served on the beach of grilled jumbo shrimp and Key Lime Pie, followed by a drink around the fire pit, listening to tales of the ever-growing size of their catch by a group of New York bankers on a boys’ fishing break. 

The next day, after a stop just off the highway at Islamorada for a fulfilling breakfast of pancakes at the Green Turtle Inn, turned out to be one of the most delightful of our trip. 

It was spent at the Dolphin Research Center, where assistant Erica Wisniewski introduced us to her family of dolphins and sea lions, many of whom have been rescued from injury. 

My daughter Marina was fascinated to watch the dolphins receiving their daily medical check-up and then even more delighted to have the chance to tickle the tummy of one playful individual, who turned out to be a descendant of Flipper, the star of the hit 1970s American TV series. 

A visit to this non-profit centre was uplifting and it was easy to understand how battle-damaged American military personnel, many of them Vietnam veterans, are among those who relish the chance to spend time with the empathetic dolphins. 

An introduction to an aquatic resident of a rather less playful nature came with a visit to the Hungry Tarpon, a restaurant just off the main highway at Islamorada. 

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After a delicious lunch (of conch fritters and blackened grouper with coleslaw and sweet potato fries) an invitation to “feed the tarpon” was met by blank looks from us, none of whom had ever heard of this fish. 

But we were encouraged to get a bucket of bait and toss it at these enormous things, that don’t have teeth but give the appearance of small sharks in the way they lunge for the titbits being dangled by people perched on the jetty. 

Pelicans vie to get the food first and the whole experience left us helpless with laughter as people shrieked at getting close to what were indeed very hungry tarpon. 

Now it was time to head for Key West, the best-known island and the one that definitely has a funky, semi-Caribbean vibe, thanks to its closeness to Cuba, just 90 miles away. 

Our base was the Southernmost Beach Resort, a collection of wooden houses painted in pale grey and yellow, with white verandas. 

The airy bedroom was shaded by a palm tree through which you could catch a glimpse of the ocean at the southernmost point of the USA. 


Shops on Duval Street, Key West, Florida (Image: Getty Images/Lonely Planet Images

The ceiling fan was hypnotic when you lay down for a siesta to escape the humidity of the afternoon, and waking up in the heavy mahogany bed amid crisp linen sheets, it was easy to imagine yourself transported to a plantation owner’s house. 

For those who deemed the climate too tropical for sightseeing (not us!) the hotel has two pools, with a tranquillity pool for adults only. 

All had plenty of sunloungers and parasols, crucial for when the sun reached its zenith. 

However, there was little time for sunbathing, with the next adventure waiting in the form of Captain Jim – a sea dog with his greying hair in a ponytail and a penchant for playing Eric Clapton on his motorboat – who was to take us landlubbers on an expedition into the Gulf of Mexico in search of dolphins. 

Cap’n Jim certainly knew how to find them and soon we were rewarded with a pod of bottlenose dolphins playing around the boat. 

When they bored of entertaining the humans, it was time to weigh anchor for an hour of blissful snorkelling, mesmerised by sea urchins feeding off the coral reef. 

Cruising back was one of those lovely, sublime journeys, listening to the music with a beer in hand, watching the colours of the sky mature from vivid reds and orange into salmon pinks and lilacs. 

Sunsets on Key West live up to their reputation – the next night we saw another spectacular display, this time from the comfort of a wonderful restaurant in Mallory Square called Bistro 245. 

We had a feast of tuna sashimi and tempura prawns, while a fi re-eater performed to the sightseers gathered to watch the sun slowly dipping below the horizon. 

There was just time to enjoy one more portion of that famous Key lime pie, this time a version dipped in chocolate and frozen on a stick. 

Truly tasty and ultimately very cool – just like Key West.

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