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I am a newbie when it comes to sailing. I do want to buy my own liveaboard someday. I have 2 questions.

1) What is the largest trailerable boat that is possible without having to use a semi flatbed?

2) What is the smallest boat that will suffice for liveaboard status that can handle some offshore passages?

I don''t plan on crossing the atlantic in a straight shot, just shorline cruising and short blue water crossings, such as miami-bahamas or nova scotia-greenland.
 

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Your beam is going to max out at 8''6" to trailer the boat without a permit. Any trailer or item being moved on a road in excess of 8''6" or 102" requires a permit according to the Title 49, FMCSR''s. Some states will require escorts as well. Daylight movement only. Length will be resticted to about 30'' or so.

I would suggest that you look very closely at boats....an 8''6" beam is very narrow inside, especially after you take the thickness of the hull on both sides and everything else inside....it could get very tight....
 
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