I know nothing about this topic, so thought I should pass along this email from MR reader Edward Dixon:
Having benefited from your advice on restaurants, I thought I would pass on some simple tips for the identification of interesting boats & interesting sailors.
The method is actually a little like finding an interesting restaurant: most of the boats you see are more or less in the form in which they left the boatyard that built them. You can think of them and their owners as being akin to chain restaurants. These are the ones to ignore!
Watch instead for boats:
– Ignore anything suggested of a racing pedigree
– Equipped to sail. Two masts are better than one. Gaff rigs and junk rigs are also interesting indicators. The limited speed but unlimited range are attributes of sail that act as a sort of filder.
– extra hardware bolted on top, like a solar panel / wind-vane combination
– A complicated-looking wind-vane attachment bolted onto the stern indicates self-steering gear
– A cupola or dome, a little reminiscent of a turret on top of a WWII bomber somewhere on the coach-roof.
– Indications that the boat is a home-build – possible harder for you to assess
Boats with quirks tend to contain interesting people; often they have made Unconventional Life Choices, including of course long sea voyages, often solo. They have often made extraordinary efforts to go to sea – I once met a man in late middle age who had crossed the Irish Sea in an easterly gale in a 17ft open boat he had constructed himself using (non-marine-grade) plywood, and who was engaged in a boat-based camping tour of Ireland. This turned out to be entirely consistent with the rest of his history.
Interesting boat folk, like interesting restaurants, are out there to be found, once you learn a few heuristics.