I was going to take the train to Portland, Oregon (after, yes, dipping my wheels in the sea) and go from there to Portland, Maine - so I'm thinking I should end up in Bar Harbor, Maine - also just north of Portland. (Sort of going for symmetry...)
Now I just have to figure out how to get from the Mackinac Bridge down to Ann Arbor, and decide whether to veer south to Pittsburgh or plow on across Canada (and go by Niagra Falls!). See more of my family? Or avoid a several-hundred-mile detour? I'm not that decisive, yet.