I can tell you abut a few places...
Charlotte Harbor is a great place to start out of. Boca Grande on Gaspirilla (I'm sure I spelled it wrong) Island is a neat little town. Millers Marina has good access and the town is a few blocks away. Good Resturants, Lighthouse Hole (at Millers), Pink Elephant, and Loons on a Limb. South Beach grill is a neat beach bar/resturant. The loose Caboose has some of he best home made Ice Cream around. The island has a great trail for skating or biking and neat shops.The next island south is Cayo Costa, which is a nature preserve. I think you need a dingy to get in there (the last time I was there I took a 16 foot cat so beaching wasn't a problem). Going north from there Venice Inlet is good, but its the first inlet I would attempt, there is Stump Pass but if you don't have local knowledge I suggest you stay clear of it. Going south you have Fort Myers and Naples and I've not been that way via boat.There is a gunkholers guide for SW Florida that you might want to pick up. I got it for my uncle (who is out of Englewood) and he seems to have found it to be valuable.