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If anything’s gonna happen, it’s gonna happen out there”

-Captain Ron

One of my all-time favorite movies is Top Gun, but that has nothing to do with this story. Another of my all-time favorites is Captain Ron, and that has a lot to do with this story. For whatever reason (perhaps the movie being one of them), delivery skippers have earned a less-than-stellar reputation as beer-swilling, fun-loving dudes with long hair and eye-patches. Ironically, my example of “good professionalism” referred to my friend Moxie Marlinspike, who, minus the beer swilling and eye patch, fit that description pretty well yet was the best and most professional skippers I’ve ever met.

For freelance professionals like Moxie and myself, the yacht delivery business is a seat-of-the-pants sort of gig. It’s often feast or famine – I’ve gone months without so much as an inquiry, then suddenly the phone won’t stop ringing and it’s back-to-back-to-back offshore trips without so much as a day of rest.

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But that’s why we do it. There are companies that specialize in yacht delivery, like PYD out of the UK, but us freelancers are different. We work for ourselves and we work for adventure. We work because, when we’re doing a job, like sailing a Cherubini schooner offshore from Tortola to Bermuda, it just doesn’t seem like work.

My first delivery was as crew on a yacht sailing from Charleston, South Carolina, to Tortola, a fall trip south in November, after hurricane season and before the winter gales began off the US East Coast. I got the call the night before departure and had to drive nine hours from Annapolis to Charleston to make it on time. We spent the majority of a day surveying the boat, fixing odds and ends, and making about 15 trips to the local West Marine for spare parts and supplies. I took the owner’s truck to Sam’s Club and spent $400 on food, which we piled aboard. We stocked 80 gallons of water in one-gallon jugs, just in case our onboard fresh water tanks failed (they did). After 12 hours of scrambling, we left the dock, dropped the owner off at the last marina in Charleston before the open ocean, set sail and didn’t look back. With three of us on board, the watches were three hours on, six hours off, which for the first few days were exhausting.

We found the easterly Trades almost immediately, which was unfortunate for us, for our course was just south of east. And close-hauled, the vent in the forward berth, where my stuff happened to be, leaked like a sieve. For 11 full days we sailed like this, hard on it in 20 to 25 knots of breeze, making for an incredibly uncomfortable, wet and tiring passage. But I was on watch when we first sighted land, the lights of Tortola looming beyond the horizon in the darkness before the dawn, and all at once it was worth it.

My first delivery as skipper was in the Caribbean. I sailed a Lagoon catamaran from St. Martin to Dominica, a passage of only a few hundred miles. We departed Anse Marcel on the northernmost French side of St. Martin and sailed east, again into the Trades, making for Tintemarre before we could tack south and try to lay our course. From the comfort of the cat’s flybridge helm station we enjoyed the opposite of that Tortola trip – smooth sailing on a fast boat, making 9 knots and more, with a warm trade-wind breeze and clear nights. We made Roseau on the southwest side of Dominica only 40 or so hours after departing St. Martin. It was around 4 AM, and we sailed close enough along the shore to watch the headlights of cars driving by. It was a moonless night, and our only instructions for finding our mooring were to sail south of the cruise ship dock and look for three bright white lights – the Chinese restaurant – where our mooring would be. We found it, albeit after a bit of stress, and Shanon (my only crew) and I sat on the foredeck drinking a well-deserved beer as we watched the sky high above the mountainous island grow brighter with the coming daylight.

For some reason, I get the feeling that the proper yacht industry has a “different” opinion of us freelancers. The image of a captain in his dress uniform, sporting epaulets and a white beard, is what comes to my mind when I try to conjure the yachting world. Yet myself and the few friends that share my lifestyle are equally qualified if not equally attired, often holding multiple licenses in multiple countries, from US Coast Guard Master Mariner to RYA Yachtmaster Oceans, with the accompanying insurance record to legitimize them. We’ve paid our dues at the yachting schools (literally) and at the helm (figuratively). We must be jacks-of-all-trades, simultaneously engineers, stewards and chefs, and we must keep our often less-experienced crew running smoothly. We frequently have varied experience in other fields, from Wilderness First Aid (which has come in handy offshore) to leading adventure travel programs around the world. We sail different boats, ranging from a 32foot sailboat my friend Matt Rutherford sailed solo across the North Atlantic, to multi-million dollar schooners like the Kauri, on which my good friend Peter Horner sailed nearly around the world.

The yacht delivery business is but a niche in the greater yachting industry, and the good yacht delivery captain is devoted to filling that need, however small, in search of the adventurous lifestyle. Capt. Epaulet, you can have your fancy uniform, white beard and monthly paycheck. I’ll take my foul-weather jacket, three-day-old scruff and a Force 8 on the nose anytime. I’ll choose adventure.

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Andy Schell
Andy Schellhttp://59-north.com
Andy Schell is a professional sailor, writer and the event manager of the ARC Caribbean 1500. You can find him online at 59-north.com.

So Caribbean you can almost taste the rum...

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