Head for MDI, being sure to get up the sound to Soamesville. Stop at Frenchboro/Long Island on the way west.
Your time window is relatively short - you could spend the whole time in Penobscot Bay. You'll have to save the Jonesport area for the next trip.
For your list, Merchants Row off Stonington, Sand Cove on Marshall Island, go through Eggemoggin Reach (just to do it). I don't know that I'd take your tri into Camden inner harbor - it's kinda tight, but you could certainly do a pass-through - as I recall, the schooners go CCW. Do Tenants Hbr you last evening in Penobscot - have lobster at the Cods End (pick a rock out of the basket for opening the claws).
But, you've read our journals (I think). E-mail me if you haven't.