Key West – Gateway to the Caribbean

For cruise passengers, Fort Lauderdale, Florida is the ideal stepping stone from the United States to set off to explore the Caribbean.

A necklace of small coral islands spanning 110 miles from the southern tip of Florida, the Keys are both exotic and all-American. Warmed by subtropical seas, cooled by trade winds, life along the palm fringed beaches embrace a sassy, sultry sense of place more akin to the West Indies.

A yachting and fishing paradise island

A yachting and fishing paradise island

Key West is the final stop at the end of the 123 mile Highway, crossing 42 bridges linking all the Keys. By ship, it’s a gentle overnight 12 hour journey.

Key West is my kinda town. Lazy, leisurely, laid back and charmingly artistic and cultural. This southernmost town of continental USA, just 90 miles from Cuba, it’s a casual “anything goes” beach resort with a fascinating maritime history and inspiring literary heritage. It’s a tropical paradise.

The Silver Shadow docked on 8 January at Mallory Square pier, right in the centre of the shopping markets, bars, bistros, boating marinas and visitor attractions.

Cigar city

Cigar city

Whether you are interested in the stories of pirates and shipwrecks, the regular vacational visits by several US Presidents, experience deep sea fishing or scuba diving, there’s fun and games, wildlife and water-sports, music and museums for all ages.

Crab cake eggs benedict

Crab cake eggs benedict

To set you up for a busy day of sightseeing and adventures, enjoy a slap up brunch at Two Friends (512 Front Street). Expect hearty platters of scrambled eggs with smoked salmon and hash browns, or an ingenious Crab Cake Eggs Benedict, washed down with a strong coffee or, more likely, a Bloody Mary. Cuisine in Key West centres on the freshest seafood – conch, lobster, crab, tuna. mahi, oysters, with a diverse choice of American, Cuban, Mexican and Italian food. Local specialities are, of course, rum and Key Lime Pie.

The best way to explore all the highlights is a hop on, hop off Trolley Bus tour. Tickets are valid for two days to allow a comprehensive tour through the streets of traditional clapboard houses visiting all the highlights around town.

Old Town Trolley Tour

Old Town Trolley Tour

On our tour, we had the chance to encounter with Louie. He is a stand-up comedian while sitting in the driver’s cab. Over the course of the 90 minute round trip, all the passengers were in hysterics with his running commentary which was informative witty and wise. “Eating and drinking is allowed on board, just no alcohol. Disguise it in a Coke bottle, I don’t mind” (This is a very cool, crazy. live and let live place). Turning a corner onto a quite residential street he says “watch this” before keeping pace with a strolling couple on the side walk and going off-script “Ladies and gentlemen I wouldn’t walk along here – this is the heart of the crime district!…” (Key West is extremely safe).

Louie says he is asked all the time – where is Hemingway’s house? He stops right nearby you can’t miss it. We hopped off here to tour the Hemingway Home and Museum where the eminent Nobel and Pulitzer Prize winning writer lived from 1931 for ten years.

Ernest Hemingway

Ernest Hemingway

It was a case of serendipity or a twist of fate which had led to his initial stay. Arriving on a P&O steamer from Cuba in 1928, he had been due to pick up a Ford motor car, but a delay in it’s delivery meant that he had to stay for a number of days. Finding the atmosphere to his liking and the fishing excellent he embraced the bohemian rum-drinking artistic culture. Key West became his inspirational literary muse.

Hemingway's Study

Hemingway’s Study

Walk around his home at 907 Whitehead Street, to see his artwork, family photographs, dining table, bedroom, bathrooms and library of books (from Steinbeck to Shakespeare) which remain intact. It’s as if he has just gone out for an afternoon fishing for marlin or a round of drinks at Sloppy Joe’s, his ghostly presence lingering on the long shaded veranda and in his spacious garden study. Here he typed from 6am to 12 noon daily, completing seventy per cent of his novels and memoirs including To Have and Have Not, For Whom the Bell Tolls and Death in the Afternoon. A selection of first edition novels in various languages are displayed in the house.

Some books from Hemingway's library

Some books from Hemingway’s library

Wander around the garden and you will encounter six-toed cats, direct descendants of his own feline furry friends.

“It was dark inside Sloppy Joe’s and the bar looked like something salvaged from a boat wreck. Fans did little to move the air. As the Gellhorns sat themselves at a table, Martha had a memory from some magazine article that this might be the author’s haunt, that Mr. Hemingway might even be here, killing the hottest part of the afternoon alone”

“Ninety miles away is Cuba, where they sometimes go for drinking and dancing, where Ernest sometimes goes for peace and quiet, as if he can’t get enough of that on this four-mile island where nothing much happens.”

– from Mrs Hemingway by Naomi Wood.

Sloppy Joe’s (201 Duval Street) was owned by Hemingway’s friend and fishing buddy Joe Russell, who became the character of Freddy in To Have and Have Not. The original manuscript of this novel was found at the bar along side many of the authors personal artefacts after he died.

Sloppy Joe's

Sloppy Joe’s

The quiet pace of life and secluded sanctuary of Key West, was also beloved by the playwright Tennessee Williams, who lived here from the late 1940’s to his death in 1983. Since then over the decades contemporary writers such as Elizabeth Bishop and Judy Blume have equally been drawn to this cultural island. A literary festival takes place in January of each year featuring seminars and discussions, musical and poetry performances, book signings and receptions. January 2015 saw the 33rd such event attended by Pulitzer Prize-winning novelist Marilynne Robinson.

Robert Louis Stevenson, author of Treasure Island would surely have felt at home here, an historical place of pirates and shipwrecks where the very houses were often made from the timbers of wrecked schooners. The island became extremely wealthy in the mid 19th century,when numerous ships floundered on the reefs. Local teams of Wreckers would rescue the crew as well as salvaging the cargo and valuables on board.

Shipwreck Museum

Shipwreck Museum

Various museums tell the story of the wreckers and sunken treasure. Mel Fisher spent fifteen years trying to locate the wreck of a 1622 Spanish galleon. Groups of experienced scuba divers can join organised archaeological expeditions each year to explore the seabed to find more gold coins and jewellery.

Every evening at sunset there is a party atmosphere around Mallory Pier with live music, street theatre performances and cocktails or step on board a boat for a cruise around the bay at Happy Hour.

Sunset party at Mallory Pier

Sunset party at Mallory Pier

Just like President Harry S Truman and Papa Hemingway, visitors may well feel enriched by the artistic ambience and vivacious vibe; experiencing the sand between the toes,you may not wish to leave this magical island of dreams.

But sadly for us, we could not linger longer; the Silver Shadow set off at 5pm to set sail again, en route to the Panama Canal.

The Grand Voyage continues… .


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About vivdevlin

I am an international travel writer, specialising in luxury travel, hotels, restaurants, city guides, cruises, islands, train and literary-inspired journeys. I review dance and theatre, Arts Festivals and love the visual arts. I have just experienced an epic voyage, circumnavigating the globe, following in the wake of Captain Cook, Mark Twain and Robert Louis Stevenson.

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