It would cost well over $3000 + fuel surcharges just for the truck alone. Then there is about $500 each way to haul and to put back in the water, and another $500 each way to take the mast down and rig it back up. I also have to travel down there and spend a few days taking everything off the boat (no anchors or rode, no lines,no blocks,even a tiny shackle if left inside to bounce around while boat is being trucked, can do a lot of damage to interior). All that stuff has to be hauled separately.
More importantly, road travel damages boats - a lot. Even if I can have her fully plastic wrapped - it's going to affect the boat somehow (and complete plastic wrap is also pretty expensive). Without that - my fiberglass and teak repair bills have to be accounted for as well.
Incidentally, my insurance has no qualms with anyone sailing my boat so long as their past experience is satisfactory (i.e. they sailed similar boats in similar waters) - there isn't even a specific requirement that they'd be USCG licensed.
I had a few people answer, and I am sorting it out as best I can now.