Have you considered going south of Punta Gorda to Burnt Store Marina, on Pine Island Sound? It's been at least 10 years since we chartered from Yachting Vacations, but they featured Island Packets and we enjoyed the restaurants at Gasparilla (not waterfront) , Cabbage Key, and at 'Tween Waters Marina, where we docked overnight. We anchored and dinghied in to the first two. Anchoring was easy in both of those spots at the time. There was a restaurant at Burnt Store Marina, too, which we enjoyed.
Back then Yachting Vacations was top-rated and we can verity their quality standards from our experience. But that was then and now there doesn't seem to be anybody rating charterers like they used to. Still, you might check them out. The Pine Island Sound area was maybe too relaxing for us, otherwise we would have gone back.