The posts we’ve written so far have alluded to buying a sailboat in the Virgin Islands, but haven’t provided much in the way of detail. There are probably lessons to be learned from our experience in long-distance boat-buying, so perhaps it’s worth discussing. There were multiple stages in this process and I’m doing a shit job of remaining concise, so I’ll break this up over multiple posts. Without further ado…
The Decision
Sometime in early 2013 we started to get serious about this idea. Cat had heard enough of me talking about it. She probably realized that I needed a bit of a kick in the ass to get moving on it otherwise life would get in the way. The trip would never materialize. And if the trip never materialized, I’d end up 40 years old, fat, bitter and a pain in her ass.  That would lead to us sleeping in separate bedrooms. A few years of that would have her taking up with her yoga instructor that I incorrectly assumed was gay, resulting in me drinking way too much at the office Christmas party to compensate for my crippling depression and I’d unsuccessfully attempt to seduce the homely-but-27 year old receptionist, ending in my firing. Cat and I would get separated, our lawyers would divide everything, she’d get the kids and the house and would remarry in less than a year. I’d get the dog and a bad drinking problem, still be fat and bitter, and definitely not get remarried.
All that because I let life get in the way, didn’t go sailing, and got bitter. It’s a slippery slope.
Cat realized she didn’t want us to go down that rabbit hole and decided to take action. She built a spreadsheet to track our finances and create savings targets. We plotted our existing assets and monthly expenditures. We made estimates about the expenses of the trip (boat, maintenance, living, fees, insurance, etc). With those pieces of information, it was easy to estimate how much money needed to be saved and we were able to set up monthly goals and a tentative timeline.
Another important detail that came out during this phase was deciding that we wanted to start the trip in the Eastern Caribbean i.e., upwind. If you buy a boat in Florida with the intention of getting to the islands, you’ve got a 1500 mile smash to windward, pounding against unrelenting tradewinds and swell. I don’t consider that a pleasant thing, and I actually like sailing. Trying to remind Cat that this is a FUN TRIP while bucking into 8 foot seas and 25 knots of wind seemed like a bad way to start the journey. So we thought better of it and decided that we’d buy a boat that’s already positioned where we want to be and then take it on a downwind sleigh ride back to the East Coast via the Greater Antilles and the Bahamas on the way home. Plus, boats in U.S. waters are often intended only for day sailing and are therefore lightly equipped. The Caribbean, being that it’s far away from where all the boats are built, ought to have loads of boats that are already fitted out with all the expensive gear necessary for long distance cruising. Win/win! Well, that was the idea anyway.
In Part 2 we’ll take a look at how I went about researching the market to determine what kind of boat we could get for the money, whether the time of year makes a difference in price and availability, and if boats are cheaper in the Caribbean versus the U.S.
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