Well, I thought I'd get the forum rolling with this post.
Joan and I are planning to take Dolce Vita down the ICW this fall to Florida. We will then "jump off" from just South of Miami to Bimini, Bahamas, spending as much as 3 months making a big loop through the Bahamas, including Nassau, the Exumas, Eleuthera, the Abacos, and Grand Bahama. In the spring we will cross back to Florida and make our way back up the ICW to the Chesapeake.
Our general timetable is to head South from the Patapsco on Oct 1, and spend about 6 weeks getting to Florida. We're leaving a little earlier than is usual in order to stay as much ahead of the cold as possible, and don't plan to do an excessive amount of sightseeing on the way down for the same reason. We'll plan on doing that on the return trip North in the Spring, where the longer we dawdle, the warmer it gets!
We would seriously love to have some "buddy boats" on the way down, so anyone who is interested should please let us know.