Charter: Best Gateway Drug to Cruising?

We plotted our own course, we cast our own lines, we poured our own drinks. We absolutely lived, in every sense of the word, for several sun- and fun-soaked days.

What’s a BVI charter without a proper Painkiller? Andrew Parkinson

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Having worked as an editor in marine publishing for the better part of a decade and a half, I’ve had a few opportunities to charter. I’ve been able to witness firsthand the whole spectrum of what some refer to as the best-kept secret in vacation travel. It hasn’t been often that those situations presented themselves, but since the opportunity to charter even once is a bucket-list item for most sailors, I never took an assignment for granted—though I did manage to embarrass myself at a cocktail party, complaining about having to leave home again for a week to “go do another charter story.”

My first taste of charter on a crewed luxury yacht had all the spoils. I was a fairly green editor working at a superyacht magazine, and the boat was a 160-footer owned by a billionaire and managed by a spruce crew of 12. The experience was truly something out of a fantasy.

I didn’t come from a ton of money. Heck, when my parents finally sprung for a well-aged Hunter 31 back in the day, for which I must have been lobbying for years, I figured my dad had hit the jackpot or something. So, that first charter came with a steep learning curve for me. It began the minute I stepped foot from the dinghy—they call them “tenders” up in that stratosphere—onto the massive swim platform. I’ll never forget the chief stewardess greeting us with the most sophisticated British accent I’d ever heard. The second stewardess tonged out crisp, cool, moist towelettes that were delicately scented with cucumber mint. A third stewardess asked if we would care for a refreshment. All the other mates and stewardesses scurried off to our lavish staterooms with our bags, unpacking and pressing all of our clothes before putting them neatly away. It was five-star service at my beck and call. It was surreal. And it was quite easy to get used to. 

For years, that story assignment defined the charter experience for me—until this past summer, when I got to experience bareboating. My wife and I, plus three other couples who are friends, helmed a 54-footer for a week through the matchless cruising grounds that are the British Virgin Islands. Unlike the superyacht experience—which is like a floating Ritz-Carlton that could have been anywhere—we plotted our own course, we cast our own lines, we poured our own drinks. We absolutely lived, in every sense of the word, for several sun- and fun-soaked days. It was soulful. It was real. It was home. 

One of the best things about charter is the wide variety of experiences that exists for cruising nuts like you and me. Charter is not only what I like to call the gateway drug to yacht ownership, but it’s also the actual gateway to some of the most memorable and exceptional waterborne experiences one can have on this planet. 

You’ll find some of those ­adventures detailed in this issue, such as our award-winning ­editor-at-large Mark Pillsbury’s ­recent sailing escapades in Antigua, where he had the rare pleasure of observing—and nearly unwittingly becoming a part of—Antigua Sailing Week from the deck of a Lagoon 42 on charter. Kim Kavin, another award-winner, takes a different tack, profiling why some lifelong sailors decided to cross over to “the dark side” (see also: power) to charter the scenic Pacific Northwest. Each charterer was rewarded with memories for a lifetime. 

On the subject of tacking, you’ve probably noticed a few subtle changes in the magazine, on which our editorial team has been working passionately and tirelessly. Our goal is the same as it’s always been: to be your gateway to the cruising realm, where the spirit of adventure calls those who feel most alive when they’re on the water, who aren’t afraid to venture a bit farther beyond the reef. 

One of those changes is the evolution of our previous Food column to the all-new Sailor & Galley, headed up by longtime CW contributing editor and Greece-based charter operator Lynda Morris Childress. She delves beyond recipes and into the lives and nautical inspiration of the hands that prepare them. I hope you enjoy the first installment of Sailor & Galley

As for charter, I can confidently attest firsthand that the ­business is booming—and rightfully so. There’s never been a ­better time to make that bucket-list item a reality. No matter your means or what type of charter you decide on, there’s a unique experience out there for everyone.

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