Your chosen carrier will have to get permits for each state the boat travels thru, and there is no consistancy in regs; the permit issuer is supposed to check clearances.
I've been out of the truck business for a while, but I believe the Fed. regs require 13'6" clearance on all interstates. Even if you meet this, and I think it's going to be close, the problem is local roads. The entire route has to be checked town by town, bridge by bridge.
Not to give you concern, but during the Cuban Crisis, I was taking a truck convoy thru FL and we had a forklift on a flat bed. The marking on the bridge said we had enough clearance; we didn't, and dumped the forklift on the main road thru town during the middle of morning rush hour! What a mess!
PS: Is your "Gypsy" the boat that was owned by Jim & Marcy Wright? If so welcome to the IP family. You should sign up with the IP Discussion Group on Sailnet.net