(Okay, this may sound like a lot, but downtown Boston is pretty small, and
you can walk from one end to the other in a couple of hours.)
A lot of people skip the end of the Freedom Trail that goes to Charlestown,
but I think that's the best part. The neighborhood is really nice, the
U.S.S. Constitution is neat, and the views from the top of Bunker Hill (esp.
if you climb up to the top of the monument) are great. At the other end
(or beginning, depending) of the Freedom Trail, the Boston Common is nice,
but the Public Garden just across the street is much nicer. From there,
you can walk down Newbury St. (see below).
If you like seafood, there are lots of great options. A historic place to
get a bowl of clam chowder is the Union Oyster House, which is near Faneuil
(sort of rhymes with "manual") Hall and Quincy Market. They have good steamers
(steamed clams that you dip in butter). A number of places have lobster,
and you can get a clambake (usually lobster, chowder, and corn on the cob)
for less than $20 at some places -- the Black Rose, also near Faneuil Hall,
is an Irish pub that has this deal, as does Tia's, which is in the Marriott
right on the water, between the Aquarium (which is also fun) and
Christopher Columbus Park.
If you like Italian food, you have to go to the North End. Erin and I like
a place called Giacomo's on Hanover St. (the main drag, anyone can tell you
where it is, and I think the Freedom Trail goes down it near Paul Revere's
house and the Old North Church (of "One if by land, two if by sea" fame).
Afterward, we often stop at Mike's Pastry's for a cannoli. Pretty much all
of the little cafes on Hanover St. are also good for coffee/dessert.
Cask 'n Flagon is a good place to go before/after the Red Sox games -- tell
Chad it's like the Boston version of the Cubby Bear, where we went when he
was in Chicago.
For upscale shopping, Newbury Street is nice (we generally only window shop
there, but it's a pretty street). For more affordable shopping, try
Downtown Crossing (the original Filene's and Filene's Basement, Macy's,
If you make it to Cambridge, the Border Café is good for Tex-Mex and
margaritas, and Bertucci's has good pizza. Both are in Harvard Square. There
are short tours all the time, leaving from either Massachusetts Hall or maybe the John Harvard Statue in Harvard Yard. You can also walk down to the Charles
River, which is nice.