Sailing Lessons in the Caribbean - aka Meet the Locals

With the beach facing west, the winds coming from behind pushed us away from shore until the beach was a distant white line. I was surprised that my sailing instructor had let us float that far out, so I said something about the first-ever sailing lesson at a Caribbean resort to terminate in Mexico. “Sailing lesson?” he said. “I thought you just wanted someone from the water sports desk to add weight to the boat. I don't know how to sail.”

Bummer. But it did reinforce my theory that you always learn something about your instructor when you take a sailing lesson. Maybe not on a large, keeled boat, where there are more things to keep track of, but definitely on a small, simple sportcraft like a Hobie-Cat. After all, you and the instructor are sitting right next to each other, so you fill the long stretches between tacks (turns) with talk about your family, work, goals, and foibles. This is a gift, because when traveling overseas, you often end up customer-vendor exchanges that are as superficial as they are genial. But there's a conversational flow while sailing a small boat that doesn't happen with your waiter or with the golf or tennis pro working (relentlessly, obsessively) on your swing.

The Sailing Instructor and the Library

On a day when the breeze was light and the intervals between turns were especially long, one sailing instructor confided to me about having been born to a crack addict mother who'd had no interest in raising him. She handed him off to an older brother, he explained. “but he was still a kid himself, and he started taking drugs, too, so I was on my own. I taught myself how to be presentable,” he recalled. “I learned water sports by visiting a library and googling everything I could about sailing.” And I'd thought Andrew Carnegie was a self-made man. He added, “I don't understand parents who abandon their children. My girls are everything.”

On Anguilla, I learned something about that island's culture when an instructor offered to sail with me to St. Martin – across five miles of open water with big waves, and back. Mind you, this would have been on a boat whose length was barely 13 feet. “I'd be a little scared,” I admitted. “But it's sailing!” he exclaimed, as if that solved everything. “We Anguillans love to sail. If someone here doesn't love sailing, he is not a true Anguillan.”

Tom Cruise Sails?

Yet another instructor seemed to have that same can-do attitude – until we started to talk about our love lives. Mine's pretty simple: I'm married, I belong to AARP. The instructor was 30 years younger than me and a lot better looking, but he told me he couldn't get a date because the local girls went for taller buys (he was maybe 5' 6”). I asked him if he'd ever seen one of those old Alan Ladd movies. He had, so I pointed out that he and Ladd were the same height. Paul Newman, Tom Cruise -- short guys. We got into a discussion about how men present themselves to women; how I'd met my wife. It was the sort of talk that might normally have made us both cringe – I mean, what is this, The View? -- but out there on the water, it was fine. Meanwhile, he turned me into a better sailor. And not a moment too soon.

It was on my very next trip to the Caribbean that I went out, way out, with the rookie water sports employee who didn't know how to teach sailing -- or even how to sail, period. I looked back at that shoreline, which was growing more distant every minute, and realized I was going to need some help getting back. I said to him, "You can't give me a lesson, so do you want me to give you one?” The answer was yes, and those next two hours of tacking back to the beach on a tough, zigzag course against the wind provided a good lesson for both of us.