40' is probably a good basic limit for most people. A larger boat can certainly be single-handed, if the boat is rigged for it specifically, but it wouldn't be for the average sailor.
__________________
Sailingdog
Telstar 28
New England
You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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