After crewing on the 2015 Caribbean 1500 rally, I bought Gryphon, my 1993 Morris Justine 36, with a specific goal in mind—sailing from Maine to the Virgin Islands, with pit stops in Annapolis and Portsmouth, Virginia, where I would join the Caribbean 1500 for the last leg. Gryphon is not my first sailboat, but she is certainly my first ocean-worthy boat, and this would be my first serious voyage as skipper of my own boat.
The prospect of sailing 1,500 miles, up to 400 miles from land, in a boat that was new to me made me focus on my lists of proactive maintenance and system improvements every day for six months before departure. Despite this intense focus, I was still not able to learn what I needed to make the voyage until I actually made the voyage.
While my learning curve was steep in the months before the trip, it became even steeper once we left the dock. The intimate understanding of a boat that is necessary to prepare her seemed only to come to me after situations in which things were not working correctly. I read as many books as anyone could, and I asked questions until I feared I had become a pest. Still, I needed to go out there and have parts or systems fail and then fix them before I understood them sufficiently to go offshore with them. The way I would prepare for going offshore was by getting beaten up offshore.
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