When we arrived at The Moorings’s Tortola base last February, our 40-foot catamaran was waiting at the dock, replete with modern conveniences: electric refrigeration, electric heads that always worked, a propane stove and, of course, a compass and an anemometer. We pre-ordered some provisions from a long online list and bought the rest from a nearby supermarket and a well-stocked store on the base. We bought a block of ice to cool down the fridge and, other than replenishing the water at a handy stop, were self-sufficient for a week. We brought nothing from home but food-storage bags and credit cards. That’s chartering in the modern era.

Over the years I’ve heard so many tall tales about Virgin Islands chartering in the early days—the late ’60s and the early ’70s—that I have to believe at least some of them are true. It was certainly a pioneering venture at a time and in a place that wasn’t prepared for it, aside from a good supply of warm blue waters, excellent sailing conditions and natural beauty. It drew a mixed population of entrepreneurs and adventuresome young people, mostly British, who sailed in seeking employment and a get-out-of-jail-free pass from northern winters.

I talked about those times with Verna Ruan, now a crewed-charter broker based in St. Thomas, whose first Virgin Islands experience was a camping trip on St. John, and with Ed Hamilton, also a charter broker, who arrived in Tortola from England on a raceboat with $140 in his pocket and three weeks later managed to convince Charlie Cary, an oil business retiree who founded The Moorings, to take him on. I also spoke with Patience Wales, SAIL’s former editor, who arrived in St. Thomas at the end of a circumnavigation and seriously considered staying there. “It was a wonderful, surreal life in those days, and very much off the beaten track,” says Wales.

Charterers, too, were a pioneering bunch, says Hamilton, many of them good sailors with plenty of experience and (an excellent attribute in the circumstances) a sense of humor. They braved the available transport, an Eastern Airlines midnight flight from New York to San Juan, affectionately called the “Comet” by the company and, less affectionately, the “Vomit Comet” by the passengers, then slept on the airport floor while waiting for their interisland flight.

If you chartered a boat back then, it was likely one of Dick Avery’s Pearsons out of St. Thomas; a Carib 34 or 41 from CSY in Tortola, owned by a retired dentist, Jack Van Ost, who stocked his company with a fleet of CSY 32s, 37s, and 44s (many of which are still extant and cruising the world); one of The Moorings’s small fleet of Pearson 35s and Morgan Out Island 41s; or a boat from West Indies Yachts in St. Thomas or Tortola Yacht Charters. Van Ost, Hamilton says, was the person who initiated the idea of a bareboat fleet whose owners put into charter identical boats that were easy to maintain. The boats offered the bare necessities: sails, an anchor or two, an icebox, an SSB radio and a compass (depthsounders first appeared on charterboats in 1975), and that was it.

Tourism in the Virgin Islands is not a phenomenon of the growth of chartering, though the blossoming of the charter industry certainly added to it. There were hotels, there were restaurants and there were a plethora of bars. Things were much more casual then, Hamilton says, and an incredible mix of people would show up at Marina Cay, then the most popular hang-out place for sailors and celebrities.

Wales reminds me that it’s hard to talk about the Virgin Islands sailing scene of 40 years ago and not make it sound like those were the good old days. In fact, there were no mooring buoys, sailors dumped their trash overboard and anchoring was a mystery for many people who, in their home waters, normally sailed from dock to dock. As for the boats, she continues, the tanks were not big enough, and there was no such thing as a deck shower. Engines were prone to problems, as were heads.

Probably the greatest problem for charterers in the early days was provisioning. First of all, there was no ice—not much, at any rate—and almost nothing in the way of supplies. When Ruan first arrived in the 1960s and stopped for provisions in a small market on St. Thomas, she found big wheels of yellow cheese and big barrels of pickled pork parts, mostly ears. Not surprisingly, this haul was generously washed down with rum, which was readily available. Most charterers hauled down duffels filled with food and dry ice and rationed their supplies.

On his website, Hamilton wrote about sailing in and out of every bay in the BVI to brief charterers on the area. “There were very few houses in the hills and almost no boats in the channel. It is no exaggeration to say that if you found a boat was in the anchorage, you moved to the next one.” Imagine! Those were the good old days in many ways.