Joe, you don't mention your friend's boat's draft
. Assuming they are not extreme, were I your buddy I would zero in on the Indian River area of FL's east coast. There are a large variety of marinas
in that region (from FL's Space Center and nearby Titusville on south...), he can alternate between many free anchorages
(in part behind the causeway structures, allowing one to shift to the N or S side of the causeway for protection) and using the nearby marinas
in towns with bus service
. This area is populated each Fall/Winter with snow birds from up north and finnding transient berthing (which is what he would be looking for, not indefinite liveaboard
berthing) should be no problem for him.
You might mention to him that he'll find 50+ cruising yachts anchored off Melbourne's Eau Gallie Causeway for the annual SSCA Gam this coming weekend; a good way to network with folks he'll later be meeting in the islands and a great event, too.