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Boston to Acadia Trip in Sept First Time!

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Hi. I am so glad I found this site- so much helpful info and replies. I haven't joined many forums, but have spent time reading some over the years - most aren't nearly as helpful as this one- thanks to all the moderators out there! I have spent weeks researching an upcoming adventure and would like some feedback about current plans.
Flying into Boston early September to avoid the crowds, staying at Lenox (Back Bay) for 3 days, then have to get back to airport somehow (is taxi the best way?) with luggage to get enterprise rental car (half the cost of getting vehicle in town and returning to airport), then driving to Rockport for a few days to explore Salem, Marblehead and Cape Ann areas. Next meeting some friends near Old Sturbridge area for a few days, then heading north to Maine - should we take 90 to 495 to 95 then get off where to see the coast via US 1 before Portland? What should we do around Portland for 2 days, besides maybe the observatory, eastern promenade, Head light, eating lobster, LL Bean for hubby, maybe a boat trip around lighthouses? Then heading north to Acadia, sounds like we should take Rt 1 into Brunswick to Rockland, Camden, Mt. Battie, then around to Acadia? Have reservations at Best Western just outside of Bar Harbor- reasonable rates but hope its as nice as most TA reviews... thinking maybe we should look for another place besides Bar Harbor area to stay for our 3 days here? Many were already booked weeks ago or too expensive, and we aren't B & B people. We like quiet, clean, driving (not big hikers), wildlife, photo ops. Thanks for any help you can offer! Haven't planned a big trip like this in 10 years!

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