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Cape Itinerary and is Martha's Vineyard walkable?

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I will be going to The Cape next week with my Mother-in-law. We are staying in Mashpee and planning to visit some of the small towns in the area. So far, it looks like we will arrive(by car from Pittsburgh) early-to mid evening on Monday. Tuesday will will head out early to Ptown. We plan on seeing the Pilgrim Monument. Race Point Beach, lunch at The Lobster Pot, walk around Commercial Street, drive back to Mashpee. I think we will want a good bit of time here, so dedicating the day to it. Wed: Hyannis Whale Watching, lunch at The Dolphin Restaurant, afternoon in Chatham. Thurs: Orleans, Welfleet and Truro (Atlantic Spice Co. and Truro Vineyard. Fri: My Mother-in-law ants me to see the Plymouth Plantation--I have mixed feelings about this as it seems a little field tripish--not sure it is my cup of tea--I am thinking instead of heading to Martha's Vineyard. I enjoy reading many of Linda Fairstein's novels in which she mentions a restaurant in Menemsha called The Bite. What would be the best way to tour the island and have lunch here? I would love to rent bikes, but am not sure she's up to that... Any suggestions?

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