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The legal height for transporting on U.S. highways is 13 feet, 6 inches. Many boats will, of course, have no trouble meeting this standard even on a trailer, but larger ones will need to be partially disassembled to pass under bridges and through tunnels.
If you ship a boat with your own cradle or trailer, be very sure the boat will be held securely. You will be responsible if the cradle or trailer fails. Wooden boats may do best in a custom cradle.
If your boat is being shipped on an open trailer or truck, consider having it shrink-wrapped for protection against weather damage and road dirt.
When shipping a dinghy with your larger boat, do not leave it on davits. Instead, protect it with padding to avoid damage to both vessels. Finally, pad every point which touches the deck or rails.