If you want to live free on the water you could do worse than drop an anchor in the shallow mud flats between Key West and Stock Island.
You will find a wild assortment of floating fiberglass that one can hardly describe as boats if by the term you mean a conveyance that moves. They are living quarters shaped like boats.
As always the dinghies to get to shore tend to be unnaturally large compared to the mother ship. Those are the boats that move and the larger they are the drier their occupants remain.
To go to town people tie their assorted landing craft along the sea wall that used to be occupied by houseboats which gives this stretch of South Roosevelt the name Houseboat Row.
A waterfront view.