Your captain will likely know where you can dine at night, but it does require some planning and reseverations before 4 on the day you plan to dine. Have entree selections at the ready. You are out of lobster season so that won't be a consideration.
I too would go with the sailing cat. It is a quiet time of year down there. No need to rush to anchorages. Just relax and enjoy it - without the sound of an engine in your ear.