The next best thing to being a local.

Boston

Prudential Center in Boston Boston is a great city to navigate by foot, however, it can be difficult in the summer and winter months when the climate might not be as favorable. I recommend getting a reusable Charlie Card to allow you to ride the T (Boston's version of the Subway) and buses.

If you are interested in attending a Red Sox game at Fenway, you will most likely have to buy your tickets through a third-party Web site. One Web site I trust is Stub Hub because they offer risk-free guarantee that your tickets will arrive on time and they are approved by Major League Baseball. A word of caution, since Red Sox games are so popular tickets are often sold well above face value, especially for games against big rivals or ones that are later in the season.

Cape Cod

Summer months are incredibly busy on the Cape. However, I think it is the nicest time to visit because Massachusetts can have chilly weather through May. The crowds are not so thick that they're unbearable. It is important, however, that you plan ahead and make reservations as soon as possible for campsites and hotels

Amherst and Northampton

Unless you know somebody that already lives in this area, it can be difficult to find somewhere to stay. Also, the downtowns in both of these areas do not have a lot of parking, especially at night. I recommend finding buses that will take you from the outer areas to the centers of town, or finding lodging that is walking distance from the sites you want to visit