Join Date: Nov 2009
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This is a vague question with no concrete answer. It depends on the boat, and how it's setup.
A 25' boat, with hank-on headsails, no tillerpilot or tiller clamp, and no lines lead to the cockpit can be a real PITA to singlehand. On the other hand, Bene505 singlehands his 50 foot Benetug regularly. His boat is probably extensively setup for singlehanding.
Generally speaking, I'd say that it's common to singlehand boats up to 35 or 40 feet. That's just a vague generality.
Alacrity, 1981 Tartan 33 #168