With the cost of fuel these days, I know of dozens of 50-75' boats whos owners (including myself) have decided not to take them down to FL for the winter. Two years ago, my fuel bill for a one way trip from CT down to the Palm Beach area was roughly $5000. Last fall it was $6800 and when I brought it back up this past spring, it was over $10,000

I can see a $14000 one way fuel bill now. Then add in dockage, food, "drinkables", plane tickets, ground transportation, hopefully no mechanicals and I'd be looking at a $30,000 round trip for a 50' boat.
With all that said, Dockwise can't do it because of the "Jones Act" which says a non US registered vessel can not pick up and then drop off cargo from/to US ports without making a stop outside the USA inbetween pick up/drop off.
How about one of those 300- 400 foot ocean going barges? Couldn't they crane the boats in, block them up & take them all to FL? I have called two shipping companies and both have said they researched it years ago & it was not cost effective. There must be somebody out there who has a big barge & tug sitting around & looking for work.
Any big ideas? There must be another way of thinking here.