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Fall week in Massachusetts

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My wife and I are starting to plan a trip in the fall to New England, probably Massachusetts. We will probably go in late September or early October. We would like to spend about half our time in a coastal town, and the other half enjoying the fall colors in the interior. We enjoy staying in B&B's. We live in South Texas and would most likely fly into Boston. I would appreciate any travel tips. We are in our mid 50's and it will just be the two of us. We are physically fit and enjoy walking, shopping, eating, and sight-seeing. One specific question - if we fly into Boston, I assume we will need to rent a car to get to our ultimate destination. I was looking at Nantucket as a possibility. I understand that I don't need a car on the island. Rather than pay $60 or $70 per day for a rental car that is sitting at the port for 3 days, can rental cars be returned at the port, and re-rented when we are ready to leave? That could save us a couple of hundred dollars. Thanks!

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