I can't speak (yet) for Tampa and north, but the Fort Myers/Cape Coral/Charlotte Harbor is loaded with interesting places, many of which can be reached by car. Gasparilla Island is cute and quiet. Useppa Island is boat only. Cayo Costa state park is also boater friendly.
In the Fort Myers
area there is St. James City on the south end of Pine Island and Bokeelia on the north. Pine Island can be reached by car through Matlachai, which is interesting in itself.
In Cape Coral
you can go by car to Tarpon Point where there is a pricey restaurant called Marker 92 and a jumping outdoor bar called the Nauti Mermaid. From there you can see Glovers Bight, one of my favorite anchorages
, which is reached by boat from, what else, marker 92 on the Gulf ICW
There is a large mooring
field a bit up the Caloosahatchie River operated by the city of Fort Myers
There are many other anchorages
. I would suggest you go to www.activecaptain.com
where you can log in as a guest and use their Interactive cruising guide book. There are marine charts
shots with markers showing anchorages, marinas
, obstructions etc. Each anchorage has information contributed by cruisers who have been there. There are also ratings for each.
Good luck. Enjoy both trips.