Sojourning in the Windwards, where cruising dreams live and die

In the Lagoon, the anchorage in the heart of the teeming city of St. George's, Grenada, a worn ketch of about 35 feet lies at anchor. It has obviously been there for some time. The water is too murky to reveal the boat's bottom-pellucid Caribbean water is not among the Lagoon's many charms-but surely it is as foul as the shaggy waterline and the brown bottom of the limp inflatable dinghy tethered to its stern. Gray paint peels from the steel topsides; rust streaks down from the chainplates. An uncovered, dun-colored mainsail sits on the boom, haphazardly furled. Jerrycans, stacked plastic cartons and a hard-bottomed dinghy clutter the deck. At the transom, between a self-steering vane and a wind generator, a faded flag of Sweden hangs from a staff. The residents of this floating home stay mostly below. A thin, gray-haired man appears at times under the doghouse roof; sometimes a woman joins him briefly. A dog the size of a cocker spaniel keeps a station aft of the cockpit, except when it rains, when it moves to its namesake shelter.

I don't know the story of this sad-looking vessel. It could be a happy one. But from appearances, I have to say this is not the poster boat for every sailor's cruising dream.

The dream is our private cliché: live aboard, cruise full time, hang out in the tropics, sail around the world. I have indulged this dream-who among us sailors hasn't?-but have always found reasons to stop short of acting on it. When I need more, I can find them in the Windward Islands.

Most of the popular anchorages, the likes of Admiralty Bay at Bequia, Carriacou's Tyrrel Bay and Clifton Harbour at Union Island, have a few of them-boats that carried their owners away on cruising dreams and then stopped, as though they had somehow run out of wind in one of the most reliably windy sailing places on earth.

Some look like waterborne garage sales, cluttered with more possessions than a small sailboat should be expected to hold. On the deck of a 40-foot double-ender near which we anchored in Clifton Harbour, I counted three dinghies, two outboard motors and three bicycles, plus assorted propane tanks, fuel containers and bulky parcels wrapped in tarps. I didn't see a lawn mower, but it wouldn't have been a surprising discovery.

Aged beyond their years by the ravages of sun and salt, these boats are sobering sights. But in spite of them, when in the thrall of my favorite cruising waters, the Grenadines, standing watch for sunset's green flash in the company of my cruising mate and a glass of Bordeaux, I tend to wax romantic about the cruising life.

My mate humors me for a while, but if I persist she will point to one of the aforementioned vessels and say something to the effect that the cruising life would be a bachelor's life for me, and that when she would visit at odd intervals she would expect to find me looking like Robinson Crusoe, wild-haired and bearded, sun-dried to a raisiny consistency, sitting in the cockpit, surrounded by rusting boat parts, picking at baggywrinkle.

At which point, I adroitly change the subject by asking what varieties of nasturtiums she's planning for next season's garden.

Not all cruising dreams, of course, end in dilapidated boats at perpetual anchor. We've all read the books of couples who have enriched their lives cruising for years at a time. I know people who have done it with great style and evident joy. I've noticed that it helps to be financially independent, in other words, to have plenty of money to maintain a comfortable lifestyle afloat, and to fly now and then to a base on terra firma.

A few fortunate sailors are able to lead more or less normal lives aboard their boats, pursuing careers and earning livings in exotic locales. Canadians Don and Anne Miller have spent the better part of the last 15 years in the Caribbean running a successful art business. Anne is the artist, Don her agent. Her studio is aboard their immaculate 56-foot aluminum cutter. Anne's watercolors and prints of island life sell briskly throughout the Windwards. At Tyrrel Bay, where their boat is anchored, Don will deliver a selection of prints to your boat.

The one aspect of full-time cruising that gives me pause is the danger of vegetation. I'm not referring to hostile plant life; I mean the vegetating of sailors. Sailing is strenuous work that can keep you fit. The problem is, a big part of cruising is sitting around between passages.

I like to run. Let me amend that-after decades of pounding the pavement, I feel compelled to do it to keep my tenuous grip on the slippery slope to couch potatodom. But it's hard to run and cruise. Even a short cruise corrupts my exercise ethic.

It doesn't help that the islands of the Caribbean are particularly unsuited to running. For one thing, running there is bad form. The island culture dictates a certain pace, which is definitely not the speed of running, jogging or even fast walking. There are perfectly good reasons for this. First, these volcanic islands are more vertical than horizontal. Second, they're hot; the cooling trade winds don't make it far inland. What's more, Caribbean island roads are among the most dangerous places on earth to be afoot, given their curves, hills, narrowness and the local driving style.

I suppose that could be construed as one of the charms of the Caribbean-that you can avoid strenuous physical activity without guilt. For the better part of a recent cruise, I was able to happily ignore the running imperative. Until a gung-ho fellow cruiser laced up his running shoes with an unseemly show of enthusiasm and shamed me into a jog on the peninsula separating True Blue Bay and Prickly Bay on the south coast of Grenada. As expected, the experience was too hot and steep to be enjoyable, but it had a redeeming moment. That was when I crested a hill and a view of Prickly Bay opened before me with a splendor that took away what little breath I had left. From amid the boats clustered in the turquoise water, a great spar rose to an incredible height, towering over lesser masts like a magnificent redwood among saplings. I had an inkling as to the identity of the boat beneath this astonishing rig, which I verified later by dinghy.

As I suspected, it was Velsheda, one of the restored J-Class boats. With her 184-foot carbon mast, steel topsides gleaming in navy blue paint, and brightwork and fittings reflecting the ministrations of a full-time professional crew, she is one of the world's most glamorous classic yachts. Rafted to her, flaunting the same color scheme and overall polish, was the mother ship, the owner's extravagantly proportioned motoryacht.

This was an epiphany: a 130-foot sailboat for daysailing and island visits, a palatial motoryacht to live aboard . . . the cruising life for me.