TD may be on about the bridge height in many cases. I am recalling, could be wrong here, ie VERY wrong, that many sailboats that do the "great circle" ie up the mississippi to the GL's, out to the atlantic and down and around and back up or down the mississippi do take there masts down for parts of the mississippi. With this in mind, it is possible to take the boat "ON" the water either north then west and south, or south down the atlantic, east in the gulf and north on the mississippi. You may want to look at which is shorter, easier etc etc.
OR, have the blinking thing trucked overland! might be another option.
She drives me boat,
I drives me dinghy!