having spent the vast majority of my life in the great state of massachusetts, I am not going to tell you to do the Freedom Trail, Faneuil Hall, or any other such historical-interest thing. I can advise on where to eat, what the locals do, and how to understand them. Above all, it's best to keep in mind that New Englanders tend to keep their business to themselves and expect you to do the same. First rule of New England: Connecticut doesn't count. Neither does anything south of New York.
Should you find yourself in Boston, you can and should do the following:
*the Museum of Science is a very fun place, as is the New England Aquarium. Singlehandedly either could beat the Cal Academy of Sciences to a bloody pulp, but among the many things to enjoy count an amazing three story tank with tortoises, large sharks, and awesome fish, a retro electricity show, chicks hatching live, snake handlers, tons o' taxidermy, an otter tank, and neat views.
* the Isabella Stewart Gardner museum is most famous for having Rembrandts + a Vermeer stolen and never recovered. That said it's got an amazing courtyard, great wallpaper, unique furniture, and this incredibly intimate feeling that most other museums don't.
* the MFA...I've seen and re-seen their permanent collection, which is pretty heavy on Impressionist and early American works (Winslow Homer, etc.). I still love the MFA. Their special exhibits are usually awesome also. I've seen over the years art deco, Monet, John Singer Sargent, Herb Ritts, el Greco-->Velasquez, David Hockney, the quilts of Gee's Bend, and many other exhibits.
places to eat:
*Clio (Hynes Convention Center): ken oringer. boston's foray into molecular gastronomy
*The Butcher Shop + Stir (Back Bay): barbara lynch's charcuterie and cheese shop + cookbook bookstore.
*No. 9 Park (Park St.): Barbara Lynch's original restaurant
*Oleana (Central): Ana Sortun is amazing.
*Sofra: Ana and Maura's bakery. The cookies are just incredible, and I'm not a cookie person.
*Clearflour: one of the three good bakeries, this one specializing in bread and laminates doughs.
*Hi-Rise (Harvard): my favorite of the three good bakeries, with delicious sandwiches. Do get the toast basket for breakfast and use lots of maple butter. The corn bread is excellent. If in Harvard, sit upstairs with coffee and food and feel like you're in an old timey schoolhouse.
*Sibling Rivalry (Back Bay): the brothers Kincaid duel different riffs on a shared item (a protein or veg). Everything I've had there had been quite good, and they used to have a rockstar pastry chef.
*Tealuxe (Copley/Harvard): tea and crumpets.
*Pinocchio's (Harvard): zucchini sicilian pizza, i miss you so terribly much!
*East Coast Grille (Central): now that Green St. Grille has taken a turn for the worse, East Coast reigns supreme for Carribean food, plantain goodness and fish. It gets very crowded and takes no reservations.
*Ten Tables (Stonybrook): it has only ten tables. i've heard nothing but good things.
*Craigie Street (Harvard): snooty waiters, fine French food.
*Darwin's (Harvard): sandwiches + soups for the 02138 intellectual. The Hubbard Park remains my fave sandwich, and do get some cape cod potato chips on the side.
*Redbones (Davis): pulled chicken sandwich with sweet sauce + mild sauce, and corn fritters with the bar regulars, a pint of something from the thirty beer wheel...this place sustained me through grad school!
*Helmand (Lechmere): Afghan pumpkin, eggplant, breads and delicious sauces. Get the meat, if you want, but it really isn't necessary.
places to get ice cream, and coffee:
*Herrell's (Harvard): if they have bourbon vanilla or chocolate peppermint, do indulge. The others flavors are delicious also.
*Toscanini's (Central): more purist than Herrell's (the inspiration to Ben and Jerry), people quite like the hazelnut.
*Christina's (Central): They serve malted vanilla. What more can I say? Christina's supplies plenty of restaurants (including Harvest) with fine quality ice cream.
*Espresso Royale (Copley/Hynes): your best option on Newbury, imho.
*JP Licks (Hynes/Stonybrook/Davis): my favorite for a long time was the oatmeal cookie froyo with caramel sauce. delicious. One day I was lucky enough to sample noodle kugel ice cream.
*Diesel (Davis): grad school writing dates, bright colors, and sceney lesbians.
*Dunkies: an institution that must be honored.
*The Boston Public Library (Copley) has a beautiful courtyard, John Singer Sargent murals, and now you can eat there, too.
*The Public Gardens/Boston Common (Park/Boylston/Arlington): Make Way For Ducklings + The Trumpeter Swan = YA classics.
*Fenway Park (Fenway/Kenmore): needs no introduction or explanation. Believe.
*Mt. Auburn Cemetery/Forest Hills Cemetery: Frederic Law Olmstead's cities of the dead.
*Arnold Arboretum (Forest Hills): sometimes rambling, sometimes manicured, always lovely.
*the Longfellow House (Harvard): lovely colonial house, nice gardens, vintage poet.
There are entire cities left uncovered. Harvard as an Educational Institution/Necessary Evil, or any other place of education, is unmentioned. JFK library, ditto. I make no mention of Allston, Brighton, Brookline, Southie, Dot, Roxbury, Chinatown, the North End, the suburbs, the beaches, the shopping, or the nightlife, though Somerville, JP and the South End do receive scant mention.
A couple of final tips:
1. the drivers are crazy.
2. the pedestrians are crazy.
3. dunkies is frequently a navigational tool.
4. don't mock the accent.