The Charter Charter: Lessons from Sailing Adventures
A rum drink and a water swing in the BVI: the perfect reminder you’re right where you belong.
Andrew Parkinson
Chartering is guaranteed to teach you something. Sometimes it’s a gentle lesson, such as discovering the pure joy of a quiet anchorage that wasn’t even on your itinerary. Sometimes it’s more like a slap from a wet halyard. Either way, every charter adds a few notches to your sailing know-how—and your humility.
Over the years, I’ve come to think of charter trips less as vacations and more as continuing education. Each time out, there’s a new wrinkle: a mystery beep from the nav station, a stubborn mooring ball, a provisioning mishap that results in 5 pounds of cheese slices and no coffee. And so I’ve started keeping an informal mental list—call it the “charter charter.” These aren’t hard rules, exactly, and they’re certainly not gospel, but they are things I’ve learned, usually by doing them the hard way.
Like provisioning. Charter boats are often floating paradises, but they are not bottomless pantries. Let your crew loose in a shoreside market without supervision, and you might end up with nothing but snacks, mixers and a healthy debate about whether Coffee mate counts as a dairy substitute. My advice? Appoint a provisioning captain, make a list and, above all, do not forget the coffee. Pro tip: Paper towels can double as coffee filters. You’re welcome.
Packing falls into a similar category. Every charter begins with someone dragging an oversize rolling duffel onto the dock like they’re about to fly to the French Riviera. Don’t be that person. You’ll end up wearing the same pair of shorts, the same salt-crusted T-shirt and the one hat that doesn’t fly off in 20 knots of trade wind. The rest of it? Deadweight. But if you’re a coffee connoisseur, do pack your favorite beans. Just trust me.
Your crew—whether familial or familiar—have their own internal ecosystem too. There’s always someone who insists on organizing the itinerary down to the minute, complete with tide tables, wind models and backup anchorages in three languages. Let them. Every crew needs a logistics geek. But every crew also needs a “just happy to be here” type, and someone who insists on helping out with the daily onboard chores. Like dishes. This person is a saint. Extra grog rations might be in order.
As for sailing itself, the gear might get fancier every year, but the sea doesn’t care how many USB outlets your boat has. Batteries still run down, anchorages still get rolly, watermakers may or may not decide to stop making water halfway through the voyage, and marine toilets still operate on black-magic principles. Explaining “pump, pause, pump” to a landlubbing friend is a rite of passage. So is the awkward moment when someone insists that they never get seasick—right before turning the color of Key lime pie.
Then there’s the matter of anchoring. Modern catamarans are wide, comfortable and basically floating condos—but they still swing on a single hook, and scope is not a vibe. Learn the anchoring system. Communicate. Don’t be the crew who drifts too close to the boat flying the dive flag.
Charter boats these days come tricked out with more amenities than ever. I’ve chartered some that were better equipped than my last apartment. But that doesn’t mean the experience has lost its charm. In fact, the beauty of chartering is in the freedom. You’re not locked into a set itinerary. You don’t have to tick off every must-see beach bar. Some of the best moments come when you go off-script—when weather changes your plan, or when you decide to linger an extra day in that perfect little bay because the breeze feels just right.
And those moments stick with you. That’s what chartering does. It gives you stories. Like the time we set out for what we thought would be a mellow downwind sail and ended up motoring through a dead calm, dodging squalls and learning how to make cocktails with exactly three remaining ice cubes.
The memories that matter aren’t always the picture-perfect ones. They’re the ones where you figured out something together, adjusted on the fly, and laughed about it at the dinner table. Smooth sailing is nice, but a little friction makes the lobster tails taste better and the stories funnier.
Whether you’re eyeing the Med, the Caribbean or the Pacific Northwest—or you’re not quite sure where to begin—if this is your year to finally book that long-awaited charter, get it done. Book the boat. Gather your crew. Toss your flip-flops into a duffel bag and go. The boat might be borrowed, but the dream is all yours.
May you see fair winds, light packing lists, and just the right amount of ice for your Painkillers.
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