Most states allow 8'6" before a wide load permit is required. Anything over that will require a wide load permit, and boats that are over 10' will require escort vehicles in many states.
What is your budget? That will determine a lot about what boats you will be able to afford. There are some excellent, larger trailerable boats, but many of them are newer designs and require a bigger budget.
I'd point out that there is a difference between a trailerable boat and a boat that can be put on a trailer and towed. IMHO, a trailerable boat is launchable without external assistance from a crane or travellift.
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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.