We bought a boat in the Virgin Islands. She’s a beautiful CS 36 Merlin built in Canada in the late 80s. Well found, fast, and fit for the task at hand – taking us on a many thousand mile, year-long voyage through the Caribbean and beyond. We invested months in due diligence; working with our broker, pouring over research, contracting detailed surveys, and gauging the market. Once we were finally content that she was a worthy vessel, we spent another month in contentious negotiations before we could sign the dotted line. We’ve had her set on stands on dry land, stripped her down and buttoned her up to ride out the Atlantic hurricane season. We’ve arranged insurance, caretaking, documentation, registration, and all the rest of the minutiae inherent to boat ownership that invariably require hemorrhaging cash.
We’ve also never actually seen her.
Maybe I should back up.
Cat and I are 30ish newlyweds that live and work in San Francisco. We met  back in 2011 while we were in grad school, she in New York City, I in North Carolina. The location of our fortuitous meeting was in Tortola, about a half mile down the road from where our new boat calls home, while on a debaucherous spring break trip. The Yacht Week. Perhaps you’ve seen the original Yacht Week trailer that went viral – beautiful yachts under full sail set against azure seas, scantily clad bisexual Scandinavian girls gyrating to the pulse of electronic dance hits, and skippers in uniform strutting down the dock in slow motion.
The trailer, for reference:
[youtube=https://www.youtube.com/watch?v=_wC721zLZz4&rel=0]I didn’t need any convincing beyond that. I got in contact with the organizers of The Yacht Week and thanks to a little artistic license with my sailing resume, they hired me as a skipper for two weeks of their series of 2011 spring break trips in the BVI. I found myself at the helm of a Beneteau 393 with a crew of Texas business bros and Brazilian girls, amongst a fleet of fifteen other sailboats with a hundred fifty revelers comprised primarily of European jetsetters, American business and med students (student loan rich!), and well-moneyed banker types. We sailed all day and partied all night and repeated the process from island to island. While this was an exceptional opportunity to meet a lot of fun and adventurous people in an incredible environment, I had not gone in to it with any expectation of finding a lady with whom I’d ever spend more than a few nights. But so it goes. The first night of the second week I met Cat. I chased her around the islands for 7 nights and had her heart at beer-drinking-backflip.
Before we knew it, the trip was over, and we found ourselves deciding that we ought to give it a shot. We commited to see each other when we got back to the States, which led into an intense couple years of long-distance courtship, a joint move to San Francisco, and a proposal that ended in a wedding last year.
So we met in the islands and got married a while later, but what does that have to do with blowing our savings on a boat we’ve never seen before that’s sitting on an island a few thousand miles from our home? Somewhere in between starry-eyed nights on moon-lit beaches and getting hitched, we realized that my recurring daydream of selling up and going sailing for an extended period was achievable. Not only was it possible, but a rather desirable alternative to working. She made a spreadsheet. We started saving. We stayed on track and hit our financial targets over the course of 3 years. Then we started shopping for a boat.
So that’s where we are now. We’ve got a boat, we’ve got a few bucks tucked away, and we’ve got a quitting date. We’re out of here on October 1st. Bon voyage San Francisco, sayonara office jobs.
We’re going south.
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