The phrase "Marinas & Dinning" makes me think instantly of Crows Nest in Venice. Little pocket marina with a great pub & resturant.
There are many resturants along the
ICW with docks, not all allow overnights, but some do.
Both Twin Dolphin and
Regatta Point on the Manatee River have resturants and others within walking distance.
Further inland up Tampa Bay any of the marinas are within walking distance to decent resturants. The Vinoy marina is especially nice and you get access to the amenities of the
hotel.
Tarpon Springs has great Greek
food, an artifact from its Greek immigrant past. I used to keep my
boat there. One trick I learned to beat the tourist crowds is that a number of the resturants do take out. So, I would call in a take out order, then zip over in my dink to pick it up from the back. Yum.
Clearwater municipal marina is right on the tourist strip with access to lots of resturants.
Cabagge Key is a cool place to drop in for dinner. Dont go for lunch, they just churn out junk for tourists then. Its a whole different vibe and way better
food at night. They used to have a few ricketty slips.
You can cover a lot of SW FL with 5' draft, but there are many places where you will have to stay in the marked channels.
Note: its been a long time since I lived in SW FL so best to confirm with the marinas/resturants above.