If you are seeking for beautiful coastal scenery and would like to enjoy delicious fresh seafood, charming little towns and more then maine is great choice of you..

First, keep in mind that south of Portland, beaches tend to be sandy and very popular while north of Portland, beaches are rockier although there are a few sand beaches. We prefer the mid-coast area but we're not beach people. Your family might prefer southern Maine and beach time. Portland is definitely a great place for food as it is considered one of the foodiest towns in the US. The Old Port Area has lots of shops and interesting food places. Don't miss the french fries at Duckfat or whoopie pies (anyplace in Maine). Also get a list of farmers markets. I thought the one in Bath and the one in Brunswick were very good. You might not be cooking but it's a good place to pick up freshly made pastries, cheese for snacking, etc. During August, you should find trucks by the side of the road selling blueberries in the mid-coast area.

Camden has a nice downtown shopping area almost on the water, actually, at least one shop had a balcony overlooking the harbor. Take the drive or hike up Mt Battie for stupdendous views.

Off the beaten path and Bar Harbor shouldn't even be in the same paragraph but Acadia park is wonderful and you won't want to miss it. For a quieter area, the Harpswells east of Brunswick offer some quieter places and some nice hiking areas on conservation land. You can get a map when you are there. One we liked was a short walk along the top of the rocky cliff. Another was a hike thru some woods to an inlet. Not many people around.

It's always fun to eat as much lobster as you can - comparing lobster rolls at different places. We made a pilgrimage to Waterman's Beach (near Owls Head Transportaton Museum and Rockland) for steamed lobster. The place has grown in popularity over the years but it's still the best picnic table with water view that we know. Tends to be quiet and a quiet area.

You might get a map to wineries for another way to get off the beaten path. This way we accidentally found Morse's Deli which is worth a visit even if DH doesn't like sauerkraut.

Stop at the Chicken Barn near Ellsworth for the used books on the second floor. Good place to find some reading material. It's right on Rt 1. Read the local papers for news of church suppers/benefit suppers. One time we had a great lobster dinner at a benefit for a volunteer fire dept. Last year we went to Bath for Heritage Days and enjoyed the chicken barbecue. We get baked beans at home but are willing to try them elsewhere.

Boothbay is not one of my favorite places although there are some great boat trips going out of there such as the one for Monhegan Island. Take a picnic lunch and enjoy a hike. If you get to Boothbay early, there's a private parking lot as you enter town. Very hard to find a parking spot otherwise.

Do you plan to explore Boston also?

Have you already purchased your airline tickets? If not, you might check on flying into Boston and out of Portland or Bangor, Maine or vice versa).

We enjoyed our stay at the Fisherman's Wharf Inn in Boothbay. It's not fancy, but it has a great location on the water, and the rates are reasonable with a full breakfast included.

The Coastal Maine Botanical Gardens in Boothbay are beautiful. Your son will love the forest pond they have FULL of frogs and tadpoles (I've never seen so many)!

Ogunquit is a nice town to stop for the day. The Marginal Way is a pleasant walk, and you can spend some time at the beach here. Not too far away is the Nubble Lighthouse in York. Be sure to stop for ice cream at Brown's near the lighthouse, it was the best ice cream of our New England trip, and we had a lot.

So many things to do in Bar Harbor and Acadia National Park. You'll enjoy the whale watch. I can gladly recommend Aqua-Terra Adventures for kayaking, we had a great time with them. Hike the 3 mile loop around Jordan Pond, and follow it with popovers and lunch at the Jordan Pond House. You should make a reservation here to avoid a long wait. In Bar Harbor, be sure to have breakfast at Two Cats Cafe...so quaint, and good too.

Thanks for the responses and great suggestions. Yes, we have already booked our tickets and will be flying out of Boston. Probably should have considered an alternative. I thought we might expore Boston if we had time since I know its a great city but I also realize there won't be much time depending on how we plan our days in Maine. Maybe plan for one full day/night there? I'm still not sure of the best itinerary for the Maine areas to visit and for how long so we aren't too exhausted/rushed.

Where you choose to go on your whale watch will factor into your itinerary, since this will take up about half a day. I'd suggest planning on going on it on your first full day in Bar Harbor. That way if it gets cancelled due to weather, you still have some days left to go on it. I'll make some recommendations, keeping your particular interests in mind and the fact that you have your 11 year old son with you.

I'd suggest something like this:

Aug 10 - Arrive in Boston
Aug 11 - Boston
Aug 12 - Rent car and drive to Portland
Aug 13 - Drive to Bar Harbor, check in hotel, walk the Shore Path and around Bar Harbor
Aug 14 - Bar Harbor/Acadia Natl. Park (whale watch this day, Loop Road in the afternoon)
Aug 15 - Bar Harbor/Acadia Natl Park (Explore more of Acadia, hike Jordan Pond Path, maybe bike some of the carriage roads)
Aug 16 - Bar Harbor/Acadia Natl Park (kayak tour in a.m, possibly explore the other side of MDI in the afternoon and hike the Ship Harbor Trail and Wonderland trail)
Aug 17 - Drive to Boothbay Harbor
Aug 18 - Drive to Ogunquit, stopping at Freeport on the way there
Aug 19 - Drive back to Boston, stopping at Salem on the way, and stay at a hotel near the airport if your flight is early the next day, if not can spend a little more time in Boston
Aug 20 - Flight back home