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If you are staying in Portland, plan on spending time around the Old Port and Commercial Street since it is easy to walk, full of good food, and the waterfront vibe is great. A small rental car also helps if you want a quick coastal drive to places like Cape Elizabeth, and October evenings can feel chilly near the water. For the Boston side, I once used Blue Nile Livery for an early airport pickup and it made the travel day much smoother.