Boston, the capital and largest city in Massachusetts, is one of the oldest and wealthiest cities in the nation. Boston is a city steeped in American history. Boston is a haven for university life, with over sixty colleges calling the greater Boston area home. Harvard University, in neighboring Cambridge, is the oldest college in the country. Boston is a popular shopping destination with exclusive Newbury Street offering up designer stores and boutiques, while Copley Place has an opulent variety of stylish European stores. Fenway Park, one of the most notable baseball stadiums in the country, hosts the Boston Red Sox.

Martha's Vineyard is just five miles south of Cape Cod and is a twenty mile long island. There are several distinct towns on the Vineyard, which has become a popular locale for celebrity mansions along private enclaves. Edgartown is a very proper neighborhood on the eastern side of the island, with Colonial style homes accessorized by pampered gardens. It is the oldest settlement on the island, and features a number of historic houses as well as the Edgartown Lighthouse.

Nantucket, a two hour ferry ride from Cape Cod, is the smaller, quieter, reserved sister to Martha's Vineyard. Covered in similar looking buildings, with a gray blue exterior and white trim, Nantucket has a distinct fishing/seaside look. The restaurants specialize in seafood, and the island is known for its remote location and serene beaches.

New Bedford is a whaling port and is home to one of the largest fishing fleets in the nation. Having been such a prominent whaling center in history, Herman Melville set the beginning of Moby Dick in New Bedford. The city center has been designated a National Historical Park, with its cobblestone streets and gas lanterns.

Plymouth, Massachusetts was the final landing site of the Mayflower, a replica of which stands in Plymouth harbor. Also home to Plymouth Rock, the town receives visitors by the droves looking to learn more about the history of early settlers and the original colonies. One way the area keeps the past alive is through Plymouth Plantation, a living-history tribute to the Pilgrims and the Indians.