Portland, with the harbor setting the pace

Portland makes sense when the harbor is the first orientation point. Begin among the brick blocks of the Old Port, walk down toward the wharves, and let the smell of salt and diesel settle the fact that this is still a working waterfront rather than a painted backdrop.

A cruise is most useful when it gives the islands, forts, and lighthouse approaches a shape that cannot be seen from Commercial Street. Pick one water outing that suits the weather and your tolerance for spray; there is no prize for boarding in conditions that make everyone miserable.

Keep the shore side of the day compact. A warm lunch, one bookshop or gallery, and an early walk along the Eastern Promenade leave more of Portland intact than a car full of crossed-off stops.