Sunscreen and Shoes: The Walking Vacation in Key West

All the attractions in Key West's historic Old Town are walkable, so you simply need stout walking shoes, sunscreen, a hat, and a walking map.

You learn quickly that pedestrians need to be careful in Key West even if they imagine they surely are protected on marked pedestrian crossings. The streets are full of rented bicycles, scooters and motorbikes, golf carts, and even automobiles—some old enough to look as if they’ve just arrived from Cuba. The one-way streets don’t make driving easy, even for the locals, and a walk around town shows some cars have been retired as art exhibits.

Some can still be driven; two are permanently parked!

There is plenty to distract pedestrians, but they need to be watching for everything and anything on wheels. It’s not that tourists on 2 wheels for the first time since their childhood don’t want to stop, it’s that they don’t know how to!

All the attractions in Old Town are walkable, so you simply need stout walking shoes, sunscreen, a hat, and a walking map. Free maps are available all over town. There are 2 competitive trolley/train systems that cover most places: a little Conch Train that looks like fun and stops in 4 locations with on and off capabilities, and the Old Town Trolley that has about 13 stops. They cost about the same. The train would better suit a family with children but the multi-on/off Trolley would be ideal for active visitors who feel a vacation has to be busy-busy.

It’s said the most photographed sign in Key West is the one showing you are now heading north at the beginning of US Highway1. The Old Custom House with its statue of the massive dancing couple is an easy-to-find landmark. It now houses an interesting museum that includes a reminder of the famous 7 Mile Bridge.

Florida’s short history is well documented and easily understood.

Once upon a time and long, long ago… the Keys had pirates. It was the 1700s and the pirates were there for the same reason Willie Sutton robbed banks: Because that was where the money was. Ponderous treasure galleons laden with gold and silver and sometimes emeralds would blow past the Keys on their way from South America to Spain to finance Madrid’s colonial ambitions. They sailed the same route each time. Often privateers lay in wait in heavily armed maneuverable small craft and captured their prizes.

The well those pirates used for fresh water has been identified and sits not far from a street that bears the name of the American, John Simonton, who bought the entire Key from a Spanish landowner. A signpost marks where the US Naval Station was placed to fight the presence of pirates and a painting hangs in the museum in the Old Custom House of Captain John Geiger, who came as part of that naval force and remained to be the Key West Harbor Pilot and a master wrecker who became one of the wealthiest men in Florida.

It’s a quick jump from carvings of pirates to an 1830 wood & paint figurehead now in the Old Custom House found underwater off the Middle Keys, a relic from an unknown ship that foundered on the Great Florida Reef. And it’s an easy second jump to one of the many cigar store Indians found in Key West’s cigar shops. The Cuban cigar industry brought a new wave of prosperity to Key West.

“The rebellion in Cuba against the autocratic rule of the Spanish government” starting with the Ten Years War of 1868-1878 brought thousands of Cuban workers to Key West. They became cigar workers and were followed by wealthy Cuban entrepreneurs who built large factories. By 1876 there were 29 factories and 2,100 workers who produced 62 million cigars annually!

A fire in 1886 destroyed many of the large factories whereupon a delegation from Tampa came offering inducements for owners to move. Some did, but trade unions became strong enough to fight the anti-labor owners who stayed. Those owners, too, moved to Tampa. And Americans moved also, to cigarettes more than cigars. And the Key West cigar industry slipped into bankruptcy.

John Long has been offering high-quality cigars at the Key West Cigar Club & Smoke Shop since 2009. Cuban cigars are still illegal in the United States but he feels there is another issue. “Cuban cigars lost their luster in the 1990s,” he says, “because all the dirt in their soil had depleted the nutrients.” He feels the emerging tobacco-growing areas are Nicaragua and the Dominican Republic. “They took seeds from Cuba in 1963 and played with them till they had it all worked out.”

It may change again. The Cuban problem began when Castro nationalized nearly all American-owned businesses in Cuba in the late 1960s, transferring their assets to the Cuban government without compensation. In response, Eisenhower enacted an embargo on all exports to Cuba and, just before leaving office in January 1961, severed all diplomatic ties with the country. Even today Congress remains divided and the presence of nearly 1 million Cuban immigrants who live here complicates the story. In December 2014, the “Cuban Thaw” began, but even the new travel regulations enacted in January prohibit general tourism travel.

John Long and the Key West Cigar Club & Smoke Shop. An exhibit at the Custom House Museum suggests the cigar store Indian is looking into the future of Cuban cigars.

A cigar factory would start when 2 men—often brothers—sat at a roller’s table, sometimes with only boxes to sit on. The wood for the boxes came from Ohio, the Buckeye State, and those little work places were often named “Buckeyes,” although most Cubans called their little factories “chinchales. As the factories grew, a reader would be hired and paid to read the day’s news or even episodes of a novel to the busy workers.

Although cigar manufacturing added to the prosperity of Key West, nothing had been more monumental than what preceded it; the “Wrecking Industry.” In the great age of sailing, more than 100 ships a day passed by Key West and, on average, one per week would founder on the reef. More than 1,000 ships are registered as having sunk off the Florida Keys. Visiting scuba divers today who ask any local where they might dive to find a sunken ship reputedly have been told, “Why drive farther? Throw the car in park and dive here!”

The current lighthouse opened in 1848 in its present location and was decommissioned in 1969. It’s worth a brief visit, and you have the option to climb the 88 iron steps to the top. One admission fee covers all 3 historic museums, the Custom House, the Lighthouse, and the Fort East Martello (more on that later.) But not even improved maritime maps and lighthouses stemmed the dangers to passing ships. The Great Florida Reef was just too dangerous.

The Shipwreck Treasure Museum shows the impact of shipwrecking, an industry that made Key West and many of its residents the wealthiest in Florida. Actors in costume tell the story and artifacts are displayed as exhibits from that era. Again, you can climb a tower for a panoramic view of the Keys, you can watch a brief movie, and you can try and lift a 60-pound bar of silver if your biceps are up to it.

In maritime museums we often see glistening gold treasures and forget how much those coins might have required cleaning. A Clark & White Saratoga Springs mineral water bottle rescued after years in the ocean reminds us.

There’s more to do at the Shipwreck Treasure Museum than just listen to auctioneers, and hide from undertakers trying to measure you for your coffin. There are artifacts in cases—and a rather touching small sculpture of a wrecker struggling back to shore. An exhausted small child clings to his back. This contemporary work by local artist James Martin reminds visitors that, even in such a difficult time, “by law and moral inclination the saving of human lives was the first part of a wrecker’s job,” before the salvage of any valuable cargo that would make Key West rich.

Photography by the authors.

The Andersons, who live in San Diego, are the resident travel and 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