But I’ve got a little secret. I’m not, in fact, heading off alone, inexperienced, and unprepared for this trip. At least I’m doing something about preparation.

You see, when I hatched this audacious scheme I took careful stock of my capabilities. I’m daring, perhaps, but not stupid. Before I even picked GYPSY out, before I decided on my route, I was already seeking proper training for a voyage of this magnitude.

As luck would have it, Steve Colgate’s Offshore Sailing School, one of the nation’s most respected institutions of nautical learning, happens to have a Coastal Passage Making Course run out of Tortola, a mere 15 miles from GYPSY as the pelican flies. The course is a weeklong immersion in the fundamentals of sailing the high seas. Students and instructors set out in a large vessel (ours was a 50-foot sloop) and run through the finer points of weather forecasting, night-time navigation, emergency protocol, reefing sails, and handling a yacht in ten-foot seas. You emerge after seven days with certification from the US Sailing Association for their highest level of seamanship. When I found GYPSY in St. Thomas, taking Passage Making was a no brainer.

PAST REPORTS
GR #2	April 30	So You Want to Buy A Boat...
GR #1	April 23	A New Beginning

So on Sunday I tidy up GYPSY, lock down her hatches, and catch the afternoon ferry to Tortola. My teachers and fellow students are at the boat, a 50-foot Beneteau custom-designed for the chartering company. We meet at a local restaurant in the evening for formal introductions and a rundown of our plans.

Captain of the boat is Jim Palmer, a global passage making veteran of over 20 years. He proves to be a first-rate sailor and an excellent teacher—adhering to the hands-off philosophy of clear direction and minimal interference. He’s also a constant source of informative tips that go beyond the course curriculum—knots, clearing customs, seasonal storm patterns—once we settle in on the boat he provides a non-stop stream of nautical lore.

First mate is Mick, a good-natured fellow from London who has been sailing since the mid-1980s. He is fit and thin, his face and hair bleached by years in the sun. On the boat he seems to subsist on doses of fresh fruit, canned beans and lentil soup. He’s professional, but never overbearing. His teaching approach is summed up by his favorite expression, “no worries,” a constant reminder that we are, after all, on vacation.

My two fellow students are from the east coast: Jan is a book editor from Washington DC and Gordon is a doctor in Syracuse. We all bond quickly in the dislocating experience of constant sailing and studying for our certification exam. Our plan for the week is intended to maximize our exposure to offshore sailing conditions and techniques. We’ll cruise from the British Virgin Islands to the Leeward Islands of St. Martins and St. Barts—about a 15-hour passage each way. We’ll make two night landings, sail all points to the wind, and more than likely experience substantial seas.

We leave mid-day Monday, a leisurely beat from Tortola across Sir Francis Drake Channel to the northern end of Virgin Gorda. The four-hour trip makes two things clear: my mastery of sailing is rusty after five years staring at a computer screen, and a 50-foot keel boat sails radically different than the tiny scows I’d grown up on. The winch for the jib is the size of a 5-gallon bucket, and you need all the torque it provides when you’re trimming the massive genoa in a stiff breeze. Jan and Gordon seem to be scouring the rust off their sailing skills as well. We all are, figuratively, in the same boat as far as capabilities.

The real challenge starts Tuesday, when we pull anchor at 8:00 am and motor through a cut in the reef into a driving rain and 5-foot seas. We reef the main, raise the sails, take a three-point fix, and set off beating towards St. Martin, 80 miles away. We heel over about 30 degrees from the wind, and plow methodically through the steep waves. The drama intensifies every time we tack, something all three students are still getting the hang of on a pitching boat in significant wind. Maybe it’s a repressed memory from sailing with my grandfather as a kid, but I’m a little surprised every time the helm calls out “hard to lee,” the boat points across the wind, the jib sheet is cranked in as the sails snap across the deck, and nothing gets broken or tangled in the rigging. In fact, everything goes smoothly until we hook our first fish (Jim and Mick have brought rods, and we troll under way). Mick’s rod screeches to life, and when he sets the hook we look down to see bottom just 20 feet below. Mick shouts “Come about!” and it’s a Chinese fire drill as we uncoil lines and crank in winches, tacking away from the shallow shoal. By the time we get the fish in, a barracuda, it’s been bitten in half by a shark.

Our day progresses with scheduled transitions on wheel watch, the persistent flow of sailing wisdom from Jim, a few more fish teases (Mick fights a four-foot Wahoo until it finally breaks free—leaping and spinning in the sun), and the constant pound of water on our hull. We drop the jib at dusk, and motor for the remainder of the trip. By 9 pm the loom of St. Martin (that soft glow highlighting inhabited land) appears in the distance, and at midnight we drop anchor in Marigot harbor.

The next day is a layover. We spend the morning covering materials in the course book, and the afternoon is ours to wander the quaint streets of Marigot, a decidedly French outpost with sidewalk cafes, gesticulating men and surly waitresses.

On Wednesday, we rise early and set sail for St. Barts, about five hours southeast. The morning trial is beating our way between the west coast of St. Martin and a small island (and submerged reef) about a mile off. We tack continually, monitoring a ‘danger bearing’ we set—an imaginary line beyond which the reef lies. Right in the middle of our exercise, Jim manages to land a four-foot barracuda. Once we’re past the island, we settle into our comfortable surge of cruising at seven knots and turn our attention to the sailing exam (we’re scheduled to take it in St. Barts). I wouldn’t say that Jim and Mick breech the teacher/student contract, but they clearly want us to pass, and do everything they can to make sure we’re familiar with the material (including walking through the test, question by question, coaxing us towards the correct answers).

We arrive at St. Barts mid-day, and tie up stern against break wall—so we can sit in our cockpit and watch couples wander along the promenade just a few feet away. We have a pleasant few hours for lunch and drinks at a sidewalk café, and then return to the boat for our certification test. Unsurprisingly, given our well-intentioned guidance, we pass easily. To coin a Mick-ism “No worries.”

Friday we’re under way by 6:30 am. We’ve got over 90 miles to cover back to the British Virgin Islands, and we’ll be working with a light, 10-knot breeze. By now we’ve got our routines well established—we’ve split into two teams, and we rotate with three-hour wheel watches. It’s a slow but pleasant cruise home, the sun is shining, the boat coasts gently with the wind, and we are all chatty with the prospect of finishing up the week. Mid-day we are joined, briefly, by a small pod of porpoises. We motor sail for much of the afternoon, and drop anchor at about 9 pm, our final passage complete.

Saturday is understandably anti-climactic after the challenge and excitement of our week—a quick sail to the charter docks, the rush to pack belongings, the strange, awkward farewells with people with whom I felt an intense bond. I don’t know if I’ll ever see them again, but we grew to respect and depend on each other as we learned the ropes of coastal passage making.

And now I’m back with GYPSY, anxious to get her out on the open water. I’m feeling much more capable now. Comfortable with my role as captain and cruiser. We’ve still got work to do before we can set sail, but I’m ready.