Welcome aboard! A couple ideas to explore: During the summer, a trolley runs continuously from Kilmarnock through White Stone and Irvington (tie up at Chesapeake Boat Basin). Tides Inn in Irvington would work as a direct destination
with its restaurants.
Urbanna, though not "on the bay" has many choices and a trolley.
Mathews has my favorite restaurant in the world (Southwind), but you would need to anchor
up Put-In Creek...worth it. There will soon be several other restaurants in Mathews. Have a fun summer! (I'll be watching this thread to get more ideas for my crew!)