The novel idea that lets us make our own sailing adventures

With all due respect to sliced bread, canned beer, the Internet and other great inventions, I have to ask: Has anyone seen a better idea (for sailors, at least) than bareboat chartering? I am almost as amazed by the phenomenon now as I was on my first bareboat charter some three decades ago when, on a typically hot, breezy day beside Road Harbour on Tortola in the British Virgin Islands, Charlie Cary, founder of the Moorings, handed me the keys to one of the classiest cruising sailboats of the time, a Gulfstar 50 ketch, and wished me and my crew of dazzled friends bon voyage.

What a novel idea. For the price of a stay at a mediocre resort, you can sail away to wonderful places in a boat worth a substantial fraction of a million dollars that is yours to do with as you please.

Given the supposed difficulty of sailing, the challenges posed by the sea and the unreliability of human nature, it’s a wonder that novel idea has grown into a worldwide industry that supports not only numerous charter companies, but to a considerable extent boatbuilders and the economies of small countries.

I’ve heard a few sad tales from charter operators about careless or clueless customers who did dumb things with their boats and brought them back with mangled keels or worse. But those are rare exceptions to the norm. Chartered sailboats are generally well cared for by their temporary masters, which might be explained by the fact many, if not most, charterers are boat owners who treat a rented boat as their own. Besides that, sailors are a proud lot—most of us would rather swim to a deserted island and hide under a palm tree than face the mortification of returning a boat marked by evidence of shoddy seamanship.

I suppose at this point I have a journalistic duty to disclose my own misadventures under chartered sail. I can say, knocking furiously on wood, that there haven’t been many and it’s debatable whether the most memorable was a misadventure, a bold resolution of a problem by a cool-headed skipper or a lucky narrow escape.

We had raced a storm into Key West with a catamaran. A gale was forecast, and the wind velocity was about two-thirds there as we scooted down the gulf, lifting the husky cruising cat’s windward hull in some of the gusts. It was a great ride, but what was exhilarating offshore was daunting in the harbor. Catamarans make wonderful cruising boats, but maneuvering under power in a stiff breeze is not one of their strong points.

I made a slow approach to our designated slip, which seemed prudent at the time. (In docking boats, I’ve learned, prudence is often overrated.) With the wind on the beam, going slow pretty much guaranteed that the cat would crab its way across the harbor. By the time we reached the slip, the boat was angled enough to put one of its bows on the wrong side of a piling. And I was chagrined enough to swim for that island.

The only bright side of the developing disaster was that the nasty weather was keeping would-be kibitzers in the Duval Street saloons. There was no dockside crowd to offer advice or be entertained by my boat-handling exhibition.

We managed to back off the piling. Then for lack of a better idea and motivated by visions of the cat fetching up on the towering topsides of one the fancy motoryachts ringing the harbor, I pushed the throttle forward, aimed at the center of the slip and let nature takes its course.

Everyone in the crew noticed it before I did (maybe I was closing my eyes): The slip was not as wide as the boat—there was no way we’d fit. But the die was cast. Disaster and mortification seemed inevitable.

It turned out the bows were tapered just enough to squeeze between the pilings; the rest of the boat wasn’t. The hulls pried the pilings apart as we coasted in amid a shower of splinters. The friction brought the boat to a gentle stop two feet from the dock. There was no need to rush around with dock lines—the boat was secure in the embrace of the pilings.

In response to a look from the First Mate that I interpreted as meaning, “What the hell was that?” I said, “I guess that’s what rubrails are for.” The boat indeed had particularly robust rubrails, and the only damage was to the pilings.

About that time the charter manager, having viewed the landing from his office, walked down the dock, extended his hand and said, “I guess that’s what rubrails are for.”

I’m writing about bareboat chartering, of course, which is what real (male) sailors do. We don’t ask for directions when we’re lost on the road, and we don’t hire professionals to drive our chartered boats on the water. I’ve deviated from the rule twice, however, both times with happy outcomes.

The first was easy—a Greek captain for a Greek cruise. He left the sailing to us, but when it was time to find a hidden harbor or an out-of-the-way taverna with stewed octopus to die for or to navigate the Byzantine politics of docking in crowded ports, complete with the requisite shouting, gesticulating and hurling Greek profanities, he was indispensable.

In the other case, it was simply an offer that couldn’t be refused from a charter company that wanted to put the big, plush catamaran it provided in its best light: Take a captain and you get a chef. She was his girlfriend, a delightful woman with a gift for creating celestial food in a sailboat galley.

We sailed mainly in the French Caribbean, and her meals reflected that culture’s cuisine exquisitely in the company of her excellent selection of French wine. I have a slide somewhere, but I don’t have to look for it because I still carry a vivid mental image, of our comely chef returning in the cat’s RIB from an early morning visit to a boulangerie on one of Les Saintes with a bag of freshly baked baguettes and French pastries. Life was good, even if I wasn’t the skipper.

As for the captain, he wasn’t much a sailor, but he certainly was a hail fellow who had no trouble enjoying the good life himself. We taught him something about sailing. He taught us something about partying.

Pleasant experiences to be sure, but not quite worthy to fit in the seabag full of memories I carry with me of sailing chartered boats on our own, free to craft our own adventures with full responsibility for their rewards—or their consequences.
For that I thank the visionary, whoever he or she may have been, who invented bareboat chartering, without which I would not have the great rubrail landing on my sailing resume.