Hogan is right about the lake getting choppy at times. You will have good access to restaurants at MYC, Star Island, The Oar and the Gossmans dock area. For a run to town I would ditch the dink and grab a cab to town. The walk is a solid 20 minutes, probably more, but we don't take that hike.
I reccommend Snug Harbor for good dockage at a reasonable price. Reasonable, for Montauk that is!
Good Luck
Harris