Bar Harbour doesn't have much in the way of decent anchorages or moorings. Winter Haven might be more interesting. You can take a bus from SW Harbour all over Mt. Desert Island.

The trip from Penobscot Bay to Casco Bay is a LONG Way. You might find a stop at Booths Bay from Camden or Rockport a better bet.

The Trip form Casco Bay to Portsmouth is a pretty long day. (We've done it twice -- but we sail or motor at 8-9 knots.)

Penobscott Bay is such a great place -- I'd spend more time there.