Spending two nights in either city with my wife and 14 year old boy, which would be more enjoyable? I am a foodie, my son wants to explore, and my wife loves to see all there is to see. We are also spending three nights in Boston. Thanks....ideas on what to do and restaurant suggestions are greatly appreciated.
As usual, jerrycoin provides excellent advice, checking some of the threads to the right in the More Like This column will provide some good overviews of Portsmouth NH (especially restaurants).
I just spent a spring week driving from Boston to Portland back to Portsmouth (based on those threads)
Spring drive thru the New England Coast listing several restaurants that I enjoyed
like yourself, I'm into food (and as you'll see brewpubs), and had an excellent time in both cities and it was an easy enough drive from Boston (altho, I wasn't going in the summer traffic of course)
Portland - a lot of interesting 2-3 hour cruises from Casco Bay, including one with lobsters, another one viewing seals etc
the downtown area - Commercial St. is fun (and easy) to walk around, good shopping for the Mrs. and some interesting stores (like the Cabot Cheese store with plenty of free samples, including root beer) for the kids. I always have a good time at minor league ballparks and Portland's (home of the Sea Dogs) is a nice stop, even if for only four or five innings.
Portsmouth - I haven't been, but friends said Strawbery Bank Museum was interesting - kind of a smaller Williamsburg/Jamestown Va. type set up explaining the history of Portsmouth and how it was settled.
They have a submarine museum - USS Albacore, where visitors can walk/hunch thru - tight quarters
Market Square, similar to Portland's Commercial St. area is their downtown and another easy day of walking about grabbing a coffee (or beer) some food and some shopping and local color
Some excellent outlets across the water in Kittery (along with the fort I snapped a photo of, where the 14 year old might want to bang around exploring)
And of course, both places offer some nice drives along the coast, where you can dive into the beach towns and grab a sandwich and see what's up (saw several amusement parks in the towns)
jakeal (where you been guy? miss your insights) says When Pigs Fly Bakery is a must do (and he knows his bakeries) and Petey's Summertime Seafood just down the road in Rye is supposed to be an enjoyable, 'beach' type hangout for food (I didn't make it, perhaps because it was only spring ).
I think you'll have a good time whichever way you decide. Good luck and enjoy.