1. Walk the Boston Freedom TrailIf you only have time to do one fun thing together in Boston, walk the Freedom Trail. A self-guided, 2.5-mile-long trail that meanders through the oldest part of Boston, it leads you past the city's historical most important 16 sites and acquaints you with the role Boston played in American freedom.
2. Graze in Boston Public GardenThe Freedom Trail begins in Boston Common, the oldest public park in America but that doesn't mean you have to rush through it. This pretty greensward can get crowded on fine-weather weekends, but that makes people-watching part of the fun. You may want to forgo the swan boats on the lake in Boston Common, a magnet for families out to air their infants and toddlers. The Boylston Street T Station (subway stop) at the south end of the Common will put you on the fast track to more Boston fun.
3. Admire Art in the Isabella Stewart Gardner MuseumDesigned as an Italianate villa with a central courtyard, the home that once belonged to Boston art collector Isabella Stewart Gardner is now a museum open to the public. Thanks to Gardner's enormous wealth, she was able to accumulate paintings and sculptures from around the world. Unlike the cool exhibitions one often finds in public museums, the Gardner collection is a pastiche of art from different eras, places, and styles, often displayed together in one room.
4. Drink in the Samuel Adams Brewery TourThirsty yet? The Samuel Adams Boston Brewery is, thanks to the free tasting at the tour's end, one of America's favorite fun factory tours. If you prefer to do your Boston imbibing in an actual bar, stop in at Cheers, aka the Bull and Finch Pub, where you will recognize the exterior from the classic TV show "Cheers."
5. Make a Run for Fenway ParkHome of the Boston Red Sox, Fenway Park opened in 1912 and maintains one of the last manual scoreboards in the Major Leagues. Behind-the-scenes tours are available daily, even on game days.
6. Educate Yourself in Harvard SquareCrossroads of Cambridge's academic community, Harvard Square is a dizzying collection of shops, cafes, museums, students and street performers adjacent to venerable Harvard University. If time is limited, take the free Harvard University tour, then devote the rest of your time to exploring the cavernous Harvard Coop.
7. Shop Newbury StreetThere are no temperature-controlled, indoor malls on Newbury Street. And there aren't many bargains to be found, either. (For that, head to the original Filene's Basement.) But quality hounds on vacation appreciate this elegant throwback. The street retains its carriage-trade aura and features many jewelers, silversmiths, antiquaires, and Boston originals including the always-dapper Louis, Boston.
8. Sail to Boston Harbor IslandsBoston Harbor Islands, part of the National Park System, consists of 34 islands within Boston Harbor as close as 11 miles from downtown Boston. May through October you can visit Boston Harbor Islands via ferry, shuttle, or tour boat. A fun complement to a Boston city visit, a trip to Boston Harbor Islands brings you close to both nature and history.
9. Visit the John F. Kennedy Presidential Library and MuseumTo some, he was a hero. To others, a style icon who represented America's youth and vigor. Still others thought him a rascal. Whatever your perspective, you can learn more about the 35th president of the United States, his elegant wife, his ambitious parents, and his place in American history at the John F. Kennedy Presidential Library and Museum located within a ten-acre Boston park.
10. Chow Down in Boston's ChinatownYou must be hungry by now. Alas, the one thing Boston lacks is truly great restaurants. Aside from Legal Sea Foods, where a hungry couple could faint away waiting for a table, Boston fare is unimpressive.
For an affordable, healthy meal in Boston, I recommend Chinatown, which has served students, residents, and tourists alike for generations. In addition to the many Chinese restaurants, there are also Japanese, Vietnamese, Cambodian, and Vietnamese eateries in this fun ethnic district.