Correction: An earlier version of this article incorrectly described St. Vincent as the largest of the Grenadine Islands. St. Vincent, the main island in the Caribbean nation of St. Vincent and the Grenadines, is not part of the Grenadine island chain. This version has been updated.

Sailboats moor off the shore of the island of St. Vincent in the Caribbean. (Winston Ross)

When I first learned that the parents of the woman I’d been dating had bought a 38-foot catamaran and planned to sail it around the world in a couple of years, I have to admit, a little voice inside my head whispered:


Not only did this mean that Roxy had almost certainly inherited the most important gene in the pool — the ad­ven­ture gene — but it also meant that maybe, if I played my cards right, I’d get to go sailing on that boat someday. Which is how this spring I discovered the exhilarating, addictive sport that is gliding through the seas at the mercy of the wind. And I also learned the best part: Because the boat’s owners are still learning to ply this trade, I got to be of real help, as much first mate as deckhand, making the trip all the more rewarding.

My last two sailing trips are increasingly fuzzy memories: one a quick Fourth of July jaunt on a pal’s 25-foot boat in the Fern Ridge Reservoir in my home town of Eugene, Ore., the other a harrowing journey on Northern California’s Tomales Bay at the age of 8, with a father with perhaps too strong a penchant for adventure and afternoon winds that did all they could to dunk me in the water and keep me there.

So it would be understandable if I approached a 10-day trip in St. Vincent and the Grenadines led by a couple of novice sailors with some trepidation. But there was none of that; not when we booked the flight to the Grenadines, not when we boarded the Astral Wind, not when we motored out of the harbor for the first time. I was nothing but electrified, from start to finish. And we all (obviously) survived the trip.

A crabby resident of the picture-perfect Grenadine Islands. (Winston Ross)
Lazy days

Our trip began in the Blue Lagoon, the harbor in St. Vincent, with an introduction to the affable expert sailor Raymond, a St. Vincent native who’d agreed to accompany us for the first few days, to make sure that we all knew what we were doing. We linked up with him at the docks, gleaned some advice about what kind of rum we should pick up and then headed into the city center to gather supplies.

When we returned to the ship, breakfast was ready: Another local had walked down the dock with a sack of rotis, the Caribbean version of burritos, eaten at any time of day.

Then came an inspection of the Astral Wind, which in hindsight should have rendered us a little nervous about venturing out into the Caribbean. The cat was supposed to have been equipped with a new sail, but the mooring company had failed to install it. The hatches above the galley were leaking and duct-taped. The propane grill and the wind generator weren’t working. Neither was the VHF radio.

For reasons that I’m not sure any of us really stopped to understand at that point, we took off anyway. Aaron, Roxy’s dad and our captain, said later that he figured we’d be able to sort the thing out while at sea, and we were all eager to get on the water. We’d traveled a long way to get there. So we watched the first of no fewer than eight incredible and unique sunsets on the water, drank rum punch and drifted off to sleep.

That first day, our destination was Bequia, about 10 nautical miles to the south. With Raymond effectively running the show, I mostly stayed out of the way, playing dominoes and drinking strong rum-laced piña coladas with Roxy. We got to Bequia in a few hours, and Raymond taught me how to drop anchor. We bought some fresh snapper from a man in a long wooden skiff who greeted us out in the harbor, then motored into town for a meal of conch fritters and mahi mahi and then back to the Astral Wind, in the dark, for our first night aboard. Piece of cake, that first day.

Our next destination was Mustique, a vacation getaway for the rich-and-famous likes of Mick Jagger, Prince William and Kate, and Tommy Hilfiger. Mustique is an island so exclusive that photography is discouraged, Raymond told us, presumably to prevent paparazzi from stalking the place.

With Raymond as our security blanket, I remained a lazy and sunbathing passenger that second day, too, figuring that I’d come in handy when they needed me. We made it to Mustique easily, hired a taxi to tour the celebrity mansions, sprawled out on the world-famous Macaroni Beach, shrieked at the attack of a massive land crab we’d thought was dead, and drank from coconuts that Raymond had climbed some nearby palm trees to pluck and chuck down to me.

To sail or not to sail

The next day, we were on our own. Raymond hopped aboard another catamaran on its way back to St. Vincent, and we charted a course for the Tobago Cays, a national marine park about 19 miles away as the pelican flies.

The learning curve was vertiginous, but I was eager to climb it. Triangulating our course with a chart, a guidebook of the islands and a GPS device, we set sail for Catholic Rock, a straight shot from Mustique that ferried us past the island of Canouan before we knew that we needed to make a hard turn to port (that’s left) en route to the Cays.

For boats equipped with engines, like the twin Yanmar diesels aboard the Astral Wind, there are basically two ways to sail. Both techniques begin the same way: Fire those engines up immediately upon leaving the harbor and point the boat “in the wind!,” as the captain cries out to signal the first mate to raise the main as quickly as possible, lest it get snagged on the lazy jacks that help rig the sail on the way up. Once the main is aloft, you unfurl the genoa jib, the head sail at the front (bow) of the boat, for more power and control.

Then comes a decision point: Do you sail out of the harbor, or motor out, maneuver into position and then cut the motors, relying on only the breeze? The latter approach is safer, but more expensive, because it burns diesel. The former is true sailing. It’s the part that makes your heart race.

Cheeky novice that I am, I lobbied Aaron early and often to cut those motors and sail. Donna, his wife, was (understandably) more cautious, and the two of us became devil and angel atop our skipper’s shoulders, prodding him to be more reckless or more careful. My abandon was all the more foolhardy because we still hadn’t figured out how to get the VHF radio working. Should we have struck a rock out there somewhere, we had only a tiny Nokia phone to use to call for help.

On the right tack

On our first day without Raymond’s guidance, we did it Donna’s way, motoring into position and relying on the wind only when a straight shot lay ahead of us. To make our left turn toward the Cays, we again flipped on the engines and glided easily into the harbor. We bought banana bread and barracuda from the first fisherman to greet us, and I dove into the water to swim with a half-dozen manta rays that had immediately arrived to inspect the boat. The next morning, we climbed aboard the dinghy and headed to the closest cay, home to a sanctuary of green turtles, dozens of them swimming peacefully everywhere we looked, gnawing at mouthfuls of underwater grass.

Although that approach all but guaranteed that we’d avoid running aground on any rocks lurking beneath the surface, it left us soft in the belly as seamen, especially with regard to one of the more challenging elements of sailing: tacking.

Tacking is how a sailboat turns left and right. Theoretically, it’s an easy process: The wind fills the main sail, held in place by a series of lines, on either the port or starboard side, powering the boat. To tack, a sailor releases the main from its secure position, turns the boat until the wind fills the other side of the sail and then a deckhand (me) rushes to tie it down in that spot. Easy enough, right?

Except, the first few times we tried it, we didn’t realize that tacking needed to happen in dramatic fashion, waiting until there was so much wind pushing the other side of the sail that once we released it, the main would snap right into place. Done tepidly, the sail meanders from left to right, and the lines flap in the wind, hanging up on anything in their way.

After a couple of sloppy tacks, I realized how I could prevail in my friendly “sail more, motor less” battle with Roxy’s mom. We needed more practice at this, I argued. What if the engines died? We ought to master the art of tacking so that we’re ready for anything.

So on the next day, on the sail back to Bequia, we practiced. We’d arrived in port early enough to have the entire afternoon to kill, tacking back and forth. We were clumsy at first, and I’d leave the Caribbean with the blisters on my hands to prove it, the marks of futile attempts to hang on to a line that was whipping away far too quickly for me to corral. But after three or four tries, we mastered it. Aaron would turn the boat, letting the sail fill back-wind as I stood ready to release the line. I’d wait until the perfect moment, and then thwap! The sail shot into its new position and we locked it into place. We were masters of the sea.

Walking on water

Until we arrived back in St. Vincent. Because we wanted to sleep in the harbor that night and not by the docks, we moored out in the bay, which meant connecting a line to a buoy affixed to the sandy bottom. My job was to hoist the buoy high enough out of the water so that I could run a line through it, but this required Aaron to steer the cat perfectly into position and then keep it there. Every time I’d get close enough to start looping the line into the right place, the boat would drift far enough away to make me drop the buoy back into the water. I tried to hang on to it with a boat hook, then dropped that in the water, too. Thankfully, one of the dock workers dinghied out to rescue the hook and moor us. We were safely in harbor once again.

It takes a while to get used to walking the earth after 10 days at sea. The ground floats beneath you as if it were the water and you are somehow walking on the surface. But the tougher adjustment was leaving that boat in the first place. By then, I wanted to spend the rest of my life on it.

Ross is a former national correspondent for Newsweek and the Daily Beast who now freelances in Oregon. His Web site is

More from Travel:

Travel Guide

Ski Guide

Caribbean Guide