I sail out of Naples and often sail to ft myers and up to Charlotte harbor. I do not find a lot going on in The big bay there. I stayed at Burnt Store and its nice, affordable but nothing to do there. One restaurant, pool across the street. Moved on west. Then fishermans Village in punta gorda. Los of places to eat and small shops. You can walk in the park along the shore and bike to town. They have a pool there but when we were there the wifi was bad and we need to be in touch. You can do it in a few days. That was all we found in the harbor. We went to boca grande pass and the marina there to the north. Very small, expensive restaurant and a hike to,town,. Town is quaint but not when being visited by pres bush. (42). There is a better marina north called uncle henrys. But it is a couple miles from town and you have to rent a golf cart to get from there to town. There is a big noisy ,big marina, with full boat service to the east. It was too crowded and busy for us. (Hundreds of boats). Crowded. So,that is all we found to do at charlotte harbor. If i missed something please let me know. I will be back and would like to see new places. Heading south there are lots of islands in the IC. Anchor out, explore the islands but other than cabbage key there are no,eating spots.
On south is south seas. A great spot. Lots to do for a couple days. Then near there is tween waters. A small resort with minimal dockage. Good pool, walk,around the island to a few spots. Really need bicycles here and you can rent them. Nothing south until anchoring off st james city. Dinghy To restaurant. Not much here. There Is ding darling on sanibel but shallow water there. After miserable mile you are in Ft Myers area where you thought of in the first place.
You can see the many places along the river. Most I think private.
From here under the 72 foot sanibel bridge is ft myers beach, then south to Naples, marco, and inside to,goodland, from Naples its 100 n. Miles to Marathom, 100"to key west and 100 to the dry Tortugas.
So ft Myers is a good compromise for you especially if your friends are there.