TravelHat,
The mail boat thing sounds awesome and I think she'd really like that. Is this it?
http://www.cascobaylines.com/maine-boat-tours/scenic-harbor-cruises/mailboat/ We're going for our anniversary and here's the timeline:
Fly into Boston Tuesday evening 10/07 or as early as we can Wed 10/08. Spend Wednesday & Thursday in Boston and then in the late afternoon Thursday take the train to Portland (if we don't rent a car). Then have all day Friday and Saturday in Portland, fly back home Sunday.
Right now we don't even have any lodging reserved. Any recommendations for either city on lodging?