Thanks to all for the replies. I will be booking a 6 day charter for November.
Go have fun with it!!
I lived there on our boat for some time and know the area very well. Just got back from there in January (as it so happens that is where Dad's boat was at too).
Water is very shallow in many areas and the ICW around Pine Island through to Ft. Myers (called the Miserable Mile) stinks. Other than that, you will enjoy it. GO check out Sanibel Island; anchor off of Useppa Island to go over to Cabbage Key for a $10 Cheeseburger. Charolotte Harbor is nice, but you gotta watch out for the crab traps which were plentiful in January. Other attractions would be Ft. Myers Beach. You can grab a mooring ball and everything is "dinkable". I can give you stores that are easily walkable via dink if you would like. Try the Beached Whale for a little more local environment. It is on FMB. In Charolote Harbor, go spend some money at Fisherman's Wharf. You will have to anchor WAY out from it, but you can sit at the bar and watch out over the bay. It is nice. Lots of shops there too. If you want to see how the other side lives, take a short hop down to Factory Bay in Naples. Downtown Naples, such as it is, is an intersting place to visit.
You might be able to hop down to the Key West/Marathon, but that will be a lot more time sailing and less time seeing the site. The Tortugas, one of my favorite places, is 121 miles from Ft. Myers. Absolutely a wonderful place to visit, but you would be hard pressed to make in the time alotted since it is 24 hours (and an offshore passage) there and back. You cannot (or should not) go in there at night. Many shipwrecks and even more reefs.
Watch out for the bridges going through Cape Coral. All are 55. There is probably not a lot you would want to see that way anyhow.
Take the camera. You will have more dolphin shots than film/card memory. If lucky, you will even see a Manatee. We saw several in January.
PM me with any questions. Have fun!!!!