How to Become a Dirty Sailor

We were standing in the IGA supermarket in St. George’s, Grenada, when it happened. We were in the produce section, looking at some tired limes, when a security guard walked over and stood beside us in an obvious fashion. She was gorgeous—six feet tall, powerfully built, huge, brown eyes with luxurious lashes. We smiled at her and continued shopping. She continued following us.

No matter where we wandered, she was there: on our heels in the bakery; at our side while we pondered cheese from New Zealand; and especially attentive as we selected a jug of Clarke’s Court dark rum. What was going on here?

And that’s when we realized it: We had become dirty sailors.

We looked at ourselves: floppy sun hats, sun-bleached t-shirts, well-worn sandals, the stunned look of a sailor on land. It all added up to the profile of someone who might just try to stuff a plantain down their shorts and make a run for it. Wouldn’t be the first time: yachties in the Caribbean are notorious for their thrift, and heisting veggies isn’t as unlikely as it seems.

The path to becoming a dirty sailor is no neat rhumb line. It usually begins with respectability: a family, a job, a marriage. Blue pill stuff. Fair winds and following seas. Then comes the thing that nobody expects: the wrinkle. The inciting incident. Our heroes are tossed forward, into a new world.

For aspiring dirty sailors, the inciting incident could be Empty Nest Syndrome. Or divorce—sometimes, but not always, including an affair. New love. For us, it was the pandemic. We had been noodling around the idea of sailing after we sold our business of 17 years (a Vermont B&B) and our kids had graduated college and moved out. My wife had traveled the Camino de Santiago, and soon she did it again—this time the Camino Portuguese, with me. I had done a university teaching gig in France’s Provence region one winter, and we were now officially Itching for Adventure.

Back to boats. And YouTube. It sounds cliche now, but it was easy to lose ourselves then. So we made a simple plan: buy a sailboat and figure it out. There were books, too (thank you, Lin and Larry Pardey; thank you, Rick Page), and ASA manuals to study, and knots to learn. But first and foremost, there was a boat to buy.

We found ours in Grenda, in Woburn Bay. It conformed to the “don’t risk more money than you can afford to lose” formula, a 2000 Beneteau Oceanis Clipper 381. We bought it, packed up our lives into a food-grade plastic barrel, and flew down. The broker dropped us off on our new home and then fled, and we immediately began to sweat and starve.

Along the way there were helpers: the South African who became an indispensable conduit to the world of sailing in general, and life in Grenada specifically; the electrician who sorted out our hellacious current woes; and a sailing couple who became close friends and inspired us to get out there and do it.

The first rule of realizing what it means to be a dirty sailor is that you are always hot and sweaty. Sometimes this was due to the climate. Other times this was due to boat yoga—the various contortions required to fix all the broken stuff on your boat.

We quickly learned that there was little need for clothes—unless you were dinghying in for some breakfast beers and free Wi-Fi. And when you lived mostly in swimsuits and birthday suits, the laundry didn’t pile up. Showers were on the transom. Food was simple. Rum was plentiful.

The second rule of becoming a dirty sailor is that you are always wet—it's a corollary of the first rule. Sometimes you are wet from sweat. Sometimes you are wet because the dinghy ride into the bar was sporty. Sometimes you are wet because you were sailing close-hauled, trying to get into Admiralty Bay in Bequia and the seas were pounding your hull, breaking over the cockpit, and you are now seasoned with a crust of salt. And you are wet.

And when you drop the hook in front of Princess Margaret Beach, you strip off your sodden sun shirts and swimsuits and jump in the water to rinse off the salt water with less salty water, and you sit on your transom and rinse with precious freshwater from your tanks, and you have just taken your single shower for the week.

Like other dirty sailors, we developed a routine: wait for a weather window, sail to the next island, drop the hook, fix everything that just broke on the passage, and live aboard for a few weeks. Repeat.

It’s not hard to see how this lifestyle could sun-bleach your brain as you tried to manage your burn rate. We were okay: I still taught online, and that kept us the other kind of afloat. But you could see it in the eyes of the vendors, from Tyrell Bay in Carriacou to Ste. Anne in Martinique: smile, but keep an eye on the hands and bags.

After a season sailing the Windwards we returned to Woburn Bay in Grenada. On a Sunday afternoon we did some limin’ at Roger’s Beach Bar, accessible only by dinghy. The sun arced lower. There was a band. There were intense conversations about broken windlasses and the little dive bar in Ste. Anne that was a front for a drug selling operation. There was rum.

And there were dirty sailors all around.