Book your reservations online. Take the train if you are in the Northeast, especially in autumn when you can make the travel and its accompanying foliage-viewing opportunities part of the adventure. If you are from points farther away, book your air travel as far in advance as possible. A weekend trip to Boston booked from Chicago 2 months in advance will run you about $275.An Amtrak trip from Philadelphia, round-trip, will run you in the neighborhood of $175. Note that you'll need to tack on an extra day if you are coming from far away on the train. New York to Boston is more do-able for a short jag.
Stay in a neighborhood that suits your temperament and taste. Boston's Bay Back district is reminiscent of several neighborhoods in Greater London. Its appeal is the mix of brownstones and modern restaurants juxtaposed with easy access to all points east and west. Alternatively, stay at a downtown hotel where you'll be closer to the main sites such as the Freedom Trail, which includes Faneuil Hall/Quincy Market and the Paul Revere House, among other stops (see Resources below).
Learn to speak the language. If you can't say that you've "pawked ya caw in Hawvawd yawd," you've never been--nor should you go--to Boston. But don't worry about getting the words right--just enjoy listening to the melody of this dialect.
Find your way to Fenway. If you've brought the kids, they'll thank you for pulling them away from the shopping madness at Faneuil Hall. Even if you aren't a Red Sox fan, consider going to a game. Sox fans are probably the most excitable fans in the nation. They breathe baseball in Boston the way Angelenos breathe smog and starlets. Games are held at Fenway Park, which is located in the heart of the city at 4 Yawkey way. Take the subway's (called the "T")green line and get off at either the Kenmore or Fenway stop. The "T" is divided into easy-to-read colored lines: red, blue, green, silver and orange (see Resources below).
Find your spot along the water. The view of Boston Harbor will give you chills, even when it's the middle of summer. If you can take a boat ride on the water, all the better.
Enjoy some of the best bars and restaurants in the country. Don't go to the Bull Finch Pub--a.k.a. the "Cheers" bar--unles you are such a diehard fan of the series that you can't handle the thought of going back to Des Moines without your Norm-Sat-Here mug. The bar itself doesn't resemble the set of "Cheers" in any case--it's only the outside view that was used in the famous TV sitcom. The Norm Burger may be worth it, though (Beacon Hill, across from the Public Garden).Instead, think like a Bostonian. One local recommends the now-trendy Alibi, which is in the Liberty Hotel on Charles Street, near Mass General (Massachusetts General Hospital). While there eat at Clink , so-named because it is jailhouse-themed (and is built where an actual prison once stood!). Try its amazing oyster chowder and tuna tartare.
Amble into a museum. If you've brought the tykes, visit the Boston Children's Museum, a private educational museum at Children's Wharf, 300 Congress Street. The museum features special acts as well as a host of educational treats for the family, designed to introduce kids to the world at large. You can even throw your child's birthday party there. Call the museum for more information at (617) 426-6500.Adults won't want to miss the JFK Museum located at Columbia Point in Boston. Take the "T" red line train to JFK/UMASS Station, where you can catch a free shuttle to the library every 20 minutes starting at 8 a.m. until closing in the late afternoon. Check with the museum for details on the schedule (see Resources below).
Relax and kick back. While Boston is brimming with history, culture, nightlife, delicious cuisine and some pretty tasty beers, you needn't put pressure on yourself to do more than just lie down and sleep. That's right - just relax.If you find a quaint hotel such as in the aforementioned Back Bay area, you can snuggle in with a good book and sleep, dreaming that a Kennedy has awakened you for a morning game of touch football or perhaps Paul Revere has sent you a text..
