We are flying into Boston, would like to take in a game at Fenway, JFK library, drive to Hyannis port, adding a night on Martha vineyard. Then head to stockbridge to see Norman Rockwell museum. Adding Woodstock, Kennebunkport, bar harbor, and Portland. Flying back from Portland.
On the way, we would like to stop and see a covered bridge, Halley's store, sandy neck beach, Maine coastal wildlife refuge, otter point,if time Coolidge library. Would like some beach time.
How much time should we allow in each place, we have 9-10 days? Can we do it?
I would visit the John F. Kennedy Presidential Library and Museum and Fenway Park on my first day , Then early next morning head for Hyannis and Martha's Vineyard . Overnight there, thenuse the next tthree days to visit the museum,Woodstock (New York), Kennebunkport (Maine), Bar Harbor, then you could comfortably cover the trip to Maine with the next three days.
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Wow, that is quite a packed vacation. I am sure you can do all that but I am afraid you won't have time to stop and smell the roses. You can do Fenway and JFK in 1 day. The Cape and Martha's Vineyard is 2 days in my opinion. Then heading west is another day. Then you want to go to Vermont then over to ME. That is another 1-2 days depending if in stay over. Kennebunk in itself is 1 day, Bar Harbor should be at least 2 days to take in Acadia National Park- very beautiful. Then you have Portland. You want to at least spend 1 day there before you head out. Maybe cut out Stockbridge and Woodstock and stick to the coast. You'll have more time to enjoy what you are seeing, in my opinion.