There are very few cities in which it's advisable to just wander aimlessly through all the neighborhoods. In Boston, you'll have a fine time if you stick to the downtown areas of Fenway, Back Bay, Beacon Hill, Downtown Crossing, Quincy Marketplace, and the North End.

lery, for a day trip to New Hampshire

http://www.yankeecruisah.com/kanc.html
The Kancamagus highway. When I was a child and my father drove me there for a day trip, I thought it was magical

Considering your preferred style of seeing a city, I might suggest that the Freedom Trail can actually take several days if done in depth. There are several less-known museums along the way, and I have actually spent several hours reading inscriptions on tombstones in the several very old burial grounds. You could plan your time to even attend an actual worship service at Old North Church - still a real and active church.

On Fridays and especially Saturdays you could browse stalls at Haymarket - listen to the conversations of the old-timer produce vendors. There are still some very interesting shops in North End - consignment shops, a couple of thrift stores. Poke around in some of the Italian grocers stores - on a slow day they will still let you taste various cheeses and salamis.

Go to the small Chinatown area on a Saturday AM - they still have places that hang whole dead poultry in the windows, although I do not know anyplace that still has lived caged birds on the sidewalk waiting to be dinner. Eat at one of the tiny below street level Chinese restaurants where few non-Asians eat.

Pick a nice day to go to Isabella Steward Gardner Museum and spend some time in the garden/courtyard.

Do a Kennedy day - first visit JFK's birthplace house in Brookline and then take Red Lnie of MBTA to JFK Museum and Library.

Some of these have been said before but here are some of my favorite must doo's for Boston

Harbor Islands-Take inexpensive ferry to georges island-Free water axis to other islands

Go to the TOP OF THE HUB resteraunt for a birds eye view just before sunset

Go for a stroll down NEWBERY and BOYLSON STREETS

Go to the Midevil Mannor Dinner theater for alcohol dinner and show for about $35pp

MFA and Boston Science museum

Fanuel Hall

Could take ferry to go over night to Providence Town-a very fun place straight or gay

Plymouth Plantation

Take an Odessy or Booze Cruise

Go to Aquarium

Go to Gardner Museum

See a free friday night movie at the Hatch Shell-bring blanket and munchies

You could see all of Boston in
three days as long as you don't plan
to waste time eating or sleeping.

I spent a wonderful week in Boston last Fall and easily filled my days with sights and adventures. 10 days is not too much in any great city, in my opinion. If you want to "paint with broad brush strokes" you can "do a city" in 3 days, but Iike a relaxed pace and I like to get off the beaten path a bit. We spent 2 1/2 days on the Freedom Trail!! You will LOVE Boston. Have fun!!

I live in Boston. I love it. 10 days is too much.

Other things to do, with a rental car.
Salem Mass-- the witch trials.

Hiking in The White Mountains in New Hampshire or Mount Monadnock. You can drive there in the Am, hike all day, and shower and be out to dinner that night.

Driving to the Beach, either Crane's Beach in Ipswich or driving to Cape Cod.

There's enough in New England for fun, but 10 days in Boston itself is a lot. You could also check out Lowell or The Saugus Iron Works.

A little known fun 1/2 day visit is JFK's birth home in Brookline. You can get there by subway, known as the "T" in Boston.

Have Fun.

Saving...

Bookmarking for Boston trip - same time!

Recently I was in Boston area for a family get together and visited Salem, MA. Yes, despite having grown up on the South Shore, we never got up to Salem.

Really enjoyed the Peabody Essex Museum. Didn't go to any of the 'witch sites'; rather toured the house of the seven gables and strolled thru charming city of Salem. I'm sure it's a whole lot more crowded during summer season than when I was there earlier this month. Ate a good lunch at "Finz", seafood restaurant off of Derby St. on Pickering Wharf.

We drove up to Salem; however I did note that the T stop (commuter rail) seemed a reasonable walk. For others who are using public transport, I think you also have option of taking a bus from Boston.

September is a great time to visit the coast of Maine and the lakes of New Hampshire! No crowds! If I had 10 days I would definitely rent a car and explore for 3 or 4 days.

And I would add that on weekdays this time of year, you won't need reservations up the coast or down on Cape Cod...you can just rent your car and set out on an adventure, deciding to spend the night wherever the road may take you.