The world is fraught with problems-it's time to buy a boat

"A never-ending cruise on other people's boats."

I have been refining Plan A for years. I’ve diagrammed it, mapped it and budgeted it. I’m ready to put it in action. I could pull the trigger as early as next fall.

The plan would kick in at the end of the ridiculously short sailing season here above latitude 43, when our boat would be put onto a truck instead of into winter storage. It would be hauled to Fort Lauderdale, where it would be launched, rigged, fitted out for cruising and provisioned. On a glorious day in late November, in weather more tropical than autumnal, we would set off with a crew of sailing friends for a bracing passage to the Caribbean. After landfall in the Virgin Islands, we would begin a leisurely voyage in some of the most gorgeous sailing waters on earth, through the Leewards and Windwards, down to Trinidad and Tobago and back, on our own fast boat, sojourning as we pleased, on our own schedule, with a varying cast of crewmembers joining us at exotic ports of call along the way.

This plan has some logistical and work-related challenges, but they could be overcome. More difficult to overcome is the appeal of the alternate plan.

Plan B also calls for cruising in the Caribbean, in the same robust trade winds and turquoise water as Plan A, but without the hassle of moving our boat 2,500 miles to get there. This is an old plan we’ve been following for years, and it is still such an agreeable way to indulge our craving for winter sailing that it begs the question—who needs Plan A?

Plan B is bareboat chartering, which I rank as the most important invention in sailing next to fiberglass, based on the sailing enjoyment it has created and the number of people who have experienced it.

Relatively few people were experiencing it when we had our first taste of bareboat chartering. That was in the 1970s, when the phenomenon of offering boats for charter without captain and crew was in its infancy. Long ago as that was—so long ago that Mount Gay rum sold for $2 a bottle in the British Virgin Islands—I still remember well the gracious welcome we received at Road Town, Tortola, from those pioneers of the bareboat charter industry, Charlie and Ginnie Cary, founders of the Moorings. They showed us to a Gulfstar 50 that seemed too new and immaculate to be a rent-a-boat—and really big. I will admit that at that stage of my sailing development, there was a certain thrill in the realization that I was to be the master of a 50-foot yacht, if only for a week.

That was the start of a Caribbean voyage that has gone on for nearly three decades, a voyage made in increments, on many boats with many different crews, that has taken us from the British Virgin Islands to Grenada. Today the BVI archipelago, where the odyssey started, is perhaps the world’s most popular charter sailing place. Then it was the frontier of the bareboating revolution.

We were virgin charterers in the Virgin Islands and everything was new to our fresh eyes. We discovered the limpid water and the December winds that gave us exhilarating sailing during the day and wakeful nights at anchor as they shook the boat with thundering gusts and 10-minute rain storms. We learned that Jimmy Buffet was telling the truth when he sang that you could see the loom of the lights of St. Thomas from Cane Garden Bay.

The islands and the waters they protected seemed to us a sailors’ heaven to which few were admitted. We had anchorages to ourselves, and saw few sails on the short, breezy passages between islands. No reservation was needed at Sidney’s Peace and Love Restaurant, the shack at water’s edge in Little Harbor, Jost Van Dyke, where the bill of fare consisted of a single entree, lobster boiled in a cauldron on the beach. The place was ours alone. We anchored in front of its sagging eve in a tidal cut so close to shore we swam for dinner in half a dozen strokes.

In the ensuing years, as charter companies established outposts in the lower Caribbean, we moved on, crisscrossing the Leeward and Windward islands. We know them now as old friends, from the sleek, hedonistic St. Barts down to the scruffy islands of the tiny nations of the Windwards, where we are thrilled anew by each return to the underwater glories of the Tobago Cays and never tire of the simple pleasure of lying at anchor in the busy, cosmopolitan, windward-facing Clifton harbor at Union Island, separated from the trade wind-roiled Caribbean Sea by a spit of sand.

We go for the sailing and the destinations, of course, but the enjoyment of Plan B has been enhanced by the boats themselves. In our annuls of chartering, there has been only one clunker, a doozy I’ll tell you about later. The others have been delightful to live aboard and to sail at a cruising pace, a credit to charter companies that know how to prepare their boats for picky sailors as well as to the highly evolved designs of purpose-built charter boats. As someone who has devoted years of study and practice to the science of keeping weight off of his boats, I am always amazed at how nice it is to sail with untold tons of furniture, appliances and amenities when chartering. A 48-foot catamaran we sailed was so palatial it seemed as though we were touring the Leeward Islands in a floating villa. The big monohulls we’ve chartered lately have had more bathrooms than our house, yet on our most recent Windward Islands jaunt, a boat with such an excess of water closets reached effortlessly at 9 knots. (Granted, the breeze was whistling at 25 knots.)

I only mention the boat that (he said diplomatically) fell short of expectations because it was such an exotic exception. (Don’t worry, the company that foisted it off on us went out of business long ago.) The most dramatic of its problems was the stowaways discovered after our first sunset cocktail hour when a female crewmember went below, turned on a cabin light and issued a blood-curdling scream. The stowaways had taken possession of the galley. They were encamped on the refrigerator lid. (Later we discovered they were encamped in the refrigerator, not to mention drawers, bins and lockers.) They marched on counters in phalanxes, like armored soldiers from the Star Wars era, while others, freelancers out of formation, made leisurely crossings of the cabin sole.

The cockroaches were our constant companions for the duration of the cruise. After the initial shock, we got along fine. They stayed out of sight during the day—though reaching into the fridge for a drink was an adventure—and they had the decency to eschew migrating to our sleeping quarters. As it turned out, they didn’t spoil the cruise.

Nor did the failing steering system, a present from a previous charterer who had obviously grounded the boat on its rudder. We nursed it along, steering a snaky course to Grenada. There the problem proved to be a welcome excuse to avoid the long, generally upwind return passage to St. Vincent. Instead we spent days anchored off the glorious beach called Grand Anse, immersing ourselves in the warm Caribbean and the island’s rich culture. We dinghied ashore daily on such rewarding missions as buying fish at the St. Georges market that shared quarters with the medieval looking public abattoir and hiking through the the rain forest. Funny how things always seem to work out under Plan B. Frankly, I don’t think Plan A has a chance.