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Cape Cod , Nantucket, Martha's Vineyard and Boston

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I am simultaneously planning a fall and spring trip to 2 different global regions . One is overwhelming, two is...well, a little crazy I am learning. Okay, the fall trip ....We are considering flying to Boston , driving to the Cape (maybe Ptown) as our base for 5 days and then heading back to Boston for 2 days before flying back out on the 3rd day. So, we have 6 days of sightseeing available. We wish to do this the first week in October. What are conditions like that time of year in Ptown and are most of the shops, restaurants and artisans still there at that late of a date? We love to and want to walk ...is there plenty of area and/or beach to walk? How possible or inconvenient is it to head to either Nantucket or Martha's Vineyard from there? Are single day trips( no overnighting) to those islands even possible ? Boston....we are thinking about staying at a hotel near the airport , turning in our rental car and then relying on public transportation to get to places such as the Freedom Trail and other recommended sightseeing for our Boston time. How difficult is it to navigate the transit system since we are from a state that has none so this is a bit ( okay, a LOT) intimidating! To get the BEST of the Cape feel AND Nantucket or Martha's Vineyard or both , where is the best place to base if not Ptown and would we later regret NOT staying in Ptown?

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