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Portland, ME to Boston-- A full day to sightsee. Need suggestions

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We will be arriving in Portland Maine around 2pm on the 24th of May. We plan to have a nice lonster lunch, check out the city of Portland, then have a nice dinner in the evening. We have nothing scheduled on May 25, except to return our rental car to downtown Boston by 6pm.

We are looking for fun activities/attractions to fill the day. We are 4 adults in our 30's with a love for food and drinks (one's a sommelier, one's a brewer). Museums don't really interest us, but the outdoors and history are appealing.

We will have 2 days in Boston after we return the car, so we could also use suggestions for attractions/bars/restaurants while there as well. Thanks for any help!

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