I'm probably too late on this (by a few months, ha!) but this is my area. I keep my boat at Gasparilla. Cabbage Key is great, but nothing to do there aside from eat, drink and be eaten alive by noseeums. Their marina is tiny, decent facilities though, not a lot of overnighters there. I consider it more like camping in an RV. Boca Grande has some great beaches and a few places to tie up for lunch or dinner (backside of Boca). Cayo Costa is a state park, people can camp there but no amenities on the island otherwise. Great shelling and empty beaches. Fishermen's Village in Charlotte Harbor is a good night or two. Lots within walking distance into downtown Punta Gorda. Running down to Ft Myers Beach is my favorite. Try Pink Shell Resort and Marina. Their rates are high during season, but manageable now. Boaters staying with them get full access to the resort amenities and the place is walking distance from downtown shops, bars, etc. Venice has Fisherman's Wharf Marina, good bar and restaurant there and quick walk over the bridge into downtown. These are just a few of my favorites. If you already made your trip, try a few of these next time!