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A charter cruise is a gift that keeps on giving

2024 September 1
sailing_chris-caswell

It was a Christmas morning decades ago, and I leapt down the stairs to see what was under the tree. But it wasn’t the usual mishmash of large and small packages, bearing the mix of new shirts, belts and perhaps a wallet. There was just a single package, badly wrapped because it was not only bulky, but soft and oddly shaped.


I ripped the wrapping paper off to find a bag with a drawstring holding it closed. What could it be? The cool car coat I’d been wanting? More socks than I could ever wear? Nope. It was filled with crackly, stiff fabric and it wasn’t until I’d spread it out on the floor that I realized what it was. A sail.


I hadn’t noticed, in my furious rending of the wrapping paper, that my mother had surreptitiously made a phone call and, as I was studying this 44-square-foot item, there was a knock at the front door. Two of my dad’s friends backed into the living room carrying an 8-foot sailing pram.


It was a moment that changed my life forever. Not only did I embrace sailing and, almost immediately, enough racing to fill closets with trophies, but a lifetime on the water. Not to mention a career that brings me to these pages.


It was, to use the popular advertising phrase, “the gift that kept on giving.” It led to the after-school job at a local sailboat dealer, sailing on my college team, and pursuing sailing journalism. And it was fun for the whole family. One of my early outings on Newport Bay was with my mother scrunched in the bow of the pram, clearly wondering why she had tipped off this sailing avalanche.


Again (as with many of my SAILING columns), you’re wondering “What the heck is he talking about?”


Full disclosure: In the process of all this sailing, I’ve become the poster child for bareboat chartering. 


Further full disclosure: I admit that I am a charterholic. “I have been five months and seven days since my last charter.” Applause. This is the charter issue and, as you read these pages, it’s about three months before Christmas. For me, that means two months and three weeks before I start thinking about Christmas gifts. But here’s the point.


A bareboat charter is the perfect Christmas gift. Like that sail under the Christmas tree, it is a gift for the whole family, and it keeps on giving in memories. There is never a size problem with a shirt and no more socks with little boats on them.


Yet more full disclosure: I am a bareboat charter missionary. Sir David Livingstone has nothing on me. He may have been looking for the headwaters of the Nile, but I continue to look for wonderful new bareboating experiences. So far, that has included all the BVI (of course), the Bahamas (again, of course), Thailand, Greece, Scotland, Tahiti, the Pacific Northwest, Baja California, French canals and many more. 


Slipping the contract for a weeklong bareboat charter into a box, wrapping it with ribbon, and putting it under the Christmas tree may be visually unremarkable, as with my sail bag. But, like that crackly sail, it will be a neverending delight that lasts long after the socks are past darning and the belts no longer fit.


I was 13 when I ripped that package, and it was more than a decade before I did my first charter with Charlie and Ginny Cary, when they opened The Moorings with a fleet of Alberg 35s in the British Virgins. I don’t want to disparage Alberg 35s, which are lovely sailboats, but these had no generators, no air conditioning, no blenders for piña coladas, no electric anchor windlasses. They were as uncivilized as what Dr. Livingstone found when he reached the headwaters of the Nile.


And yet, I was enchanted. The very idea of jumping on a plane (or climbing in a car for a North American charter) is endlessly appealing. Even today, when going through an airport would have dissuaded Dr. Livingstone before he left Britain, does not deter me. 


The reason? At the end of a flight (and a winning wager that my baggage will arrive at the same airport), there is a clean and shiny yacht ready for my friends and I to savor. The world, at least within bounds, is at our feet: new anchorages to explore, sandy beaches, and more than a few local pubs. 


Cunard used to have a phrase, “Getting there is half the fun,” but I can say without question that “Being there is all the fun.” I’ve done enough long ocean races to last a lifetime and the idea of spending weeks getting somewhere is, to me, a losing bet. I’d rather hand my ticket to the boarding agent, and await the warm rush of fragrant tropic air as I debark in a few hours.


And so, my counsel is this: a bareboat charter is the absolute best Christmas gift, and I say this with the permission of She Who Must Be Obeyed, who has been campaigning for a diamond bracelet that says “BTDT” which, of course, means “Been There Done That.” I take that to mean she wants me to find new bareboating destinations. 


To paraphrase Dr. Livingstone’s famous quote, “I go anywhere, provided it be forward,”let me offer: “I go everywhere, provided it be bareboat.”