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Acadia National Park

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My husband and I will be traveling from Boston to Acadia National Park in mid-September for our first visit to Maine. We also want to visit some of the coastal towns along the way there and / or on the way back. Our flight to Boston arrives at 1:00 PM on a Wednesday and then we will then pick up our rental car to head to Maine. We have five nights to see Acadia and some of the Coast. My husband and I are both in our early fifties and want to do some hiking and biking in Acadia , as well as spend some time driving to see the scenery both in Acadia and a little of the coastal area North of Acadia. If we have time, we want to do a whale watching tour(are they around this time of year?) or an afternoon sail. After researching towns to stay, it seems the most convenient and popular place to stay is Bar Harbor. We are not necessarily looking for the most touristy place to stay, but would like to be convenient to driving or biking to park, as well as walking (or short drive) to some good restaurants. Our idea of a great evening is watching the sun go down with a martini and walking to a great place to eat. Would Southwest Harbor be just of good an option than Bar Harbor.? Or does anyone have any other suggestions? We would like to spend no more that $125 to $150 a night. It can be self catering or B & B or hotel.
My next question is this. If we land at 1:00 (if on time) and get our car, we would be looking at an arrival time of 7:00 PM if we drive straight to Acadia. As much as I would rather get there the first night, it would probably be more relaxing to have a 2 1/2 hour drive up the road to one of the scenic coastal towns. Be able to walk around, watch the sun go down and have a nice dinner, We could then leisurely drive up the Acadia the next morning. It seems we need at least 3 nights around Acadia to do want we want to do and have down time. We could then spend our last night at another town on the coast a little closer to Boston (would like to be no longer than a 2 hour drive from the airport). Our flight is at 2:45 PM the following Monday.
I realize I am rambling. I need to make a decision on whether to get straight to Acadia and do our coastal touring the last 2 days on the way back to Boston. Or do 1 night on way up, and one night back down. I am thinking about whether it is better being in certain places on weekdays, week nights, weekends, etc. as far as traffic and crowds and driving are concerned. I am over thinking this!
Thanks for everyone's input on the Fodor's site!

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