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Itinerary help for Boston and Islands

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Let me know how this will work:
Day 1-3 Boston, Day 4 - Rent car drive coast to Plimouth Plantation then on to Chatham and spend night
Day 5-6 - Nantucket
Day 7- ferry over to Martha's Vinyard (spend night and leave from there next day or go back to Nantucket? Will have to compare prices of ferry, room rate etc.
Day 8- Ferry back to Hyannis to get car. Drive to Newport RI for night. See the mansions, etc.
Day 10 drive to Boston airport for departure
Questions: It could be cheaper to fly from Boston to Nantucket, no rental, no parking. Skip Newport and fly back to Boston . Sounds like a lot of hopping around while the car is just sitting in parking lot.
Any other suggestions? Maybe go north instead of south. Want to spend as much time seeing the beauty of Mass. while I'm there. We are in good physical shape and I know what activities I'd like to do and where to stay but am concerned about the itinerary.

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