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Key West, FL: For Some, the End of the Rainbow


Flying into Key West truly feels like you're landing at the end of the rainbow. The gorgeous city mixes seaside views and tourist traps with a rich history and fine dining.

There are places in America that are there because they were put there by a developer. They offer magnificent golf courses, delightful restaurants, and, of course, lots of shopping. But they all have little to distinguish themselves from each other—or to attract visitors in this new, clean, industry that has overwhelmed but invigorated the world, tourism.

Those new developed places don't exist because they were once the spot where America trundled covered wagons across its rivers. They were not battle sites where nations fought for their survival. No natural disaster, no tragedy of life happened here. Their public relations teams must despair those colorless places will ever attract visitors with money to spend, tourists.

You would expect a little block of land 2 miles by 4 at the very end of the road, literally at the south end of US Highway 1 to be similarly colorless, but instead visitors arrive to find a Technicolor extravaganza. Before we had digital cameras this was surely the place where visitors would run out of film. Key West is a photographer’s dream—and the weather is almost guaranteed to cooperate. And Key West has a history!

What’s To See?

For starters, Key West has 3,000 historic buildings, almost all occupied by owners—and most lovingly restored and maintained. Most were originally built, solidly, by ships’ carpenters, which is why they have survived the passage of time. You see white picket fences impacting trees in the garden, so what do home owners do? Why, cut the fence back so the trees can breathe easy!

Key West

Most of the homes have been recently painted, some identified as historically important and an occasional one even boasts a mural.

Some of the homes have won a place in the prized National Register of Historic Places. Many are identified with their dates and original owners and a few have won the little civic star showing approval for the restoration of the home. Art hangs everywhere, in shops, restaurants, and as fun murals, just waiting for the passing by of a smiling tourist.

Tourists do tend to smile. This can be a fun vacation although restaurants can be more pricey than in most home towns, even in the off season. Cab fare from the airport to Old Town at the moment is $9 per person. You won’t need a car in Key West. You don’t even want to drive there! Key West is the last of 45 islands, or keys, along a monotonous 113-mile roadway based on the original foundation of the FEC railway that was destroyed by a hurricane in 1935. Key West lies a total of 160 miles from Miami. Unless you have plans to stay at some of the other keys on the way from Miami—such as Marathon—you may find it easier, albeit more expensive, to fly. Key West International Airport is a delightful, well-run Old World airport with a lot of history. The first international flights out of America were those from Key West to Havana, Cuba in 1913. We all know air travel was more exciting in those days and arguably more enjoyable.

Key West

The top 3 images were taken at the airport. The tribute to pioneering aviator Augustix Parla hangs from the ceiling in El Meson de Pepe restaurant on Mallory Square.

Parking can be a problem in Old Town. Hotels vary from fairly large signature hotels to many, many small inns and B & Bs. We rented a 4-bedroom home for a 2-week family vacation and got better rates because we went in May at the start of the offseason. We have no knowledge of hotels but later will make some recommendations for restaurants.

So What to Expect?

Key West enjoys itself and doesn’t take itself too seriously. The main north and south drag, Duval Street, might appeal more to young people. Indeed the Lonely Planet travel guide once gave the Highs and Lows of Key West as Highs: “Stunning tropical fish and unparalleled views of the sea,” and the Lows: “Crass consumerism and T-Shirt shopping.”

But apart from today’s touristy scene (and most vacation cities have all that), there is a solid sense of history in this little place that shows up at the end of Highway US 1 South.

The Spanish were here first, Cubans and pirates of all nationalities, all using its natural harbor deep enough to accommodate large vessels.

The painting Spanish Conquistador Arrives in Cayo Hueso by William Hoffman, a WPA mural painted in 1936 presently hangs at the airport.

Key West took time to change from a desolate remote “inhospitable coral isle perched on the edge of a very dangerous reef” into today’s vacation island. It all started when Spain sold Florida to the United States in 1818 and 4 years later the Spanish landowner sold the island to John Simonton of New Jersey for $2,000 in 1821-22. He sold three-quarters of his interest to three partners whose names similarly were applied to the new streets they created, Whitehead, Fleming, and Greene.

Because the shipping lanes kept luring pirates, a US Naval Base with forts on Key West, and 70 miles away west on the Dry Tortugas island group, was built in 1822 with the importance of Key West rising and falling according to America’s needs. The navy base became strategic again during the Cuban Bay of Pigs threat in 1961.

Key West’s deep harbor has protected ships for more than 3 centuries with both yachts and private sailing ships anchoring in the Key West Bight on the northwest shore, and larger cruise ships now tying down at Key West Harbor off Mallory Square on the west.

The population of Key West is under 25,000 although it can double in high season especially when cruise ships are in town. The couple saying goodbye because one is going off to sea, in the figure called Contact by J. Seward Johnson is one of several sculptures in town supported by The Sculpture Foundation. The couple embracing on the dock were passengers from Brazil who kindly agreed to pose for us.

As we have said, it may be more pleasant to fly into Key West than drive; you get the immediate impression you have really arrived at the end of the rainbow! If you drive it’s not so magical. Says a writer friend, Elana Schor: “US 1 on the outskirts of town is littered with the detritus of modern life…However as you proceed south into the town center, the character changes into an ambience that’s quite Bahamian, not quite Cuban, and not quite nautical—just very Key West”

Photographs by Authors

The Andersons, who live in San Diego, are the resident travel & cruise columnists for Physician's Money Digest. Nancy is a former nursing educator, Eric a retired MD. The one-time president of the New Hampshire Academy of Family Physicians. Eric is the only physician in the Society of American Travel Writers. He has also written 5 books, the last called The Man Who Cried Orange: Stories from a Doctor's Life.

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