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Marathon, Fla.

In “Where Have All the Pirates Gone,” singer Eileen Quinn captures Boot Key Harbor in Marathon at a period in its history some sailors remember fondly, but others would happily forget.

Approaching the entrance to Boot Key Harbor, there is a much more orderly mooring field than cruisers from years ago will remember.He’ll bluff about the beaches,

The bikini babes, the boats,

And the endless sea of overproof

On which this whole myth floats.

Where have all the pirates gone?

They’re pumping gas in Marathon.

Living in some trailer park,

They sail their dreams out after dark.

A witty chronicler of the cruising lifestyle, Quinn used to introduce her pirate song with a commentary about this small city in the Florida Keys. “I liked to describe Marathon as the American Dream destination for folks without a lot of financial resources, who climbed into their decrepit cars and headed south to paradise,” Quinn says. “When their cars broke down in Marathon, that’s where they stayed — some of them still living in those cars.”

Of course, that was before Marathon’s great cleansing, which came quickly after the new millennium. “These days I think I’d be tempted to mention how cleaning up Marathon has meant that they now have to bus all the service workers in from Homestead,” she says, referring to Miami’s southern suburb.

Most of Marathon’s pirates have scattered to the wind, at least those with cars and boats capable of getting under way. But they and like-minded brethren are still out there, reminders of those old days. Should you ever find yourself down-island, you can get an earful of the old Marathon by visiting the nearest sailor bar, then listening for the loudest mouth in the place. “Crusty” or “scruffy” will describe the man behind the mouth, usually (dare I say it) a native of Florida boasting about some future accomplishment or some big score. For a sense of precleanup Marathon, take Scruffy the Sailor, multiply him mentally, seat one copy at every table in the place, and turn up the volume.

But that was not the Marathon I found when I arrived there shortly before Thanksgiving last year. My purpose was to deliver a 2006 Island Packet 440 from Bradenton, Fla., to the south coast of the Dominican Republic. Her new owners were on board for the Bradenton-to-Marathon leg, after which the other two members of the delivery crew would fly in to finish the trip with me. We chose Marathon as the best place to assemble the gear and provisions we would need for an 11-day voyage to the D.R. As a bonus, the three-day layover would allow me to investigate the harbor’s notorious past and speculate about its future.

A staff member with the Marathon Turtle Hospital shows visitors a recovering female green sea turtle.From Bradenton, we had sailed overnight to Marco Island. Under way early the next morning, we made Little Shark River at Everglades National Park in time to drop the hook to a sherbet and strawberry sunset. From there to Marathon was an easy 37-nautical-mile run across Florida Bay. You get the idea — with an average speed between 6.5 and 7 knots, Tampa Bay to Marathon makes for a leisurely three-day cruise for sailboats and trawlers. Urban South Florida is closer. Transiting from Florida’s East Coast via Hawk Channel, Marathon is about 90 nautical miles from Miami, while Key West lies about 45 miles farther down the archipelago.

As we entered Boot Key Harbor, Thanksgiving was still two days away, so the mooring field was half empty, still awaiting the flocking snowbirds. A few shabby vessels lay at anchor — and a few character boats that we photographed — but most of the vessels were conventional and reasonably well-maintained, between 30 and 45 feet. The neat rows of mooring balls made a good first impression, and the water looked clean. We brought Tides Forever alongside the bulkhead at the Boot Key Harbor Municipal Marina, whose primary mission is administering the mooring field from its headquarters in a former fish processing plant.

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