The Corsair 37 is trailerable, and a lot bigger than the Hobie 33...
Largest trailerable sailboat I know of is the Hobie 33. It's a racer that was designed to be trailered to races at locations far from home waters. Only 8 foot beam and a retractable keel.
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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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Still—DON'T READ THAT POST AGAIN.