I live in Punta Gorda and mostly do overnighters behind the barrier islands of N. Captiva, Cayo Costa, Boca Grande and Don Pedro, all of which are north of Fort Meyers Beach. I have also cruised down from Tampa to Marco Island and beyond.
There are several nice cruising destinations in this area. Most are anchorages but marinas are also nearby. Here is a run down:
Boca Grande- Nice anchorage north up the bayou from the marked inlet on the bay side. A bit skinny, maybe 5' after you make the turn to the north, but it opens up and the anchorage has 10' in the middle and 6' all the way up to the mangroves. Drop your anchor in the center and back down and tie your stern to the mangroves. Dinghy over to the public/private dock on the north end. The north half are public and the south half are for the Pink Elephant. Walk a half mile or so into town wich has a couple of restaurants and over to the beach for a swim.
Cayo Costa State Park, Pelican Bay. Just south of Boca Grande. Either anchor out- there is lots of room for big boats and 6'+ draft, or if you are a smallish boat tie up to the park docks and pay a pittance for overnight. Walk 1/4 mile or so over to the beach.
Don Pedro State Park Docks- This one is a sleeper. Go north on the ICW from Boca Grande, under the bridge and then a mile or so up look for a tiny cut to the west. Your boat needs to draw no more than 3' to make it through at low. Tie up at one of the free park docks then walk a few hundred yards across the island to the pavilion and beach.
Sarasota- Further north, there is a mooring field just south of Marina Jack's who manages the moorings. Dinghy in to the beach to the north and you are in the middle of downtown Sarasota with lots to do.
Back down south again, North Captiva/Barnacles Restaurant- 3' is about all that can do this at low. Go into the cut and around the point at the north end of North Captiva. Barnacles, a nice old Florida type of fish house is at the head of the cove. Tie up at their docks, 30ish feet is about all that fit, and go in for lunch or dinner. The restaurant is under new ownership and maybe they will be more accommodating of overnight stays than the former ones. Or you can anchor out after dinner.
Down further south, Fort Meyers Beach has a nice mooring field. The motel at the bridge manages them. The mooring field is good for up to 45' and has deep water. The dinghy dock is under the bridge and from there you can find lots of bars, restaurants and the beach is 1/4 mile to the west.
Naples has a public mooring field right in town. Don't know of any other anchorages.
Marco has a decent anchorage in Factory Bay, but not much to do or go to down there.
David