The autopilot on my 35ft sloop, Second Wind, had been both commissioned and sea-trialed. I had also completed all of the other upgrades I’d had planned in preparation for perhaps a year-long cruise through the Caribbean. Working with various local technicians, I’d added solar panels, a new water-cooled refrigeration system, a new chartplotter, air conditioning, an EPIRB, an AIS transponder, a new dinghy and outboard, and a set of Eastern Caribbean courtesy flags. I’d also added new winches at the wheel for single-handed sailing and hired a professional rigger to check my standing rigging.
Now it was time for my first solo sail, an experience that would put both Second Wind and my skills to the test. Granted, I had solo-sailed my previous boat, a 25ft C&C, on any number of occasions up in Maine. But here on the coastal waters off the town of Fajardo in Eastern Puerto Rico, I would need an autopilot if only to stay head-to-wind while raising Second Wind’s significantly larger mainsail.
Because it would be my first solo departure from my slip, I called for some assistance in casting
