If Ralph Waldo Emerson and Henry Thoreau could find transcendental inspiration in Massachusetts, surely you can too. This state has been leading America in everything from liberty to higher education since the very first colonies were founded in Plymouth and Boston. Brimming with history, culture, and natural beauty, Massachusetts guarantees its travelers will have their hands full planning an itinerary.

Besides the urban star power of Boston, most visitors head to the coast. Between Cape Cod, Martha’s Vineyard, and Nantucket, it’s easy to slip back into another era when sea captains milled around and wealthy bluebloods escaped their city digs for a weekend at the beach. Head inland to travel through the historic farming region of Pioneer Valley or venture far west to the perennially popular Berkshires Mountains.

It’s hard to label Massachusetts a bargain destination, but deals can be found during the winter months. The simple fact is the area is loaded with picturesque towns with even quainter inns and the buzz of Boston so there is something to do any month of the year. While not cheap, the lodging from the Berkshires to the Cape is deliberately charming. By land or by sea, people want to visit and for the most part, the locals are very welcoming if not off-put by their New England accents. Besides the superlative history, the state excels in its seafood. All along the coast, modest cafés hide superb clam chowders and steamed lobster dishes.

The centrality of Massachusetts to the rest of New England ensures all kinds of extended trips into neighboring states. It’s also completely feasible to travel from the coast to the Berkshires in a day, though you’ll certainly want to take your time cruising along some of America’s prettiest roads. One particular highlight is whale watching off Cape Cod, though the annual star attraction is simply the changing leaves each fall.

With so much to see between the major regions of Massachusetts, deciding not to rent a car would be regrettable. Half the fun is getting from point A to point B, as the roads are incredibly scenic and marked with timeless, colonial-era towns along the way. The one area where you could get by without a vehicle is along the coast. Water taxis make traveling between Boston and the Cape a real pleasure. Though once on Martha’s Vineyard, it’s likely you’ll wish you had your own set of wheels to explore this amazing island.


  • Walk between Boston’s historic neighborhoods and envision the city as it began shaping the course of America centuries ago
  • Go whale watching off the coast of Cape May in summer for reliable sightings of blue and pilot whales
  • Indulge your appetite in the cozy, but exquisite seafood restaurants on Martha’s Vineyard and Nantucket
  • Pick you own apples in fall at a farm in the Pioneer Valley, the core of Massachusetts’ traditional agricultural region
  • Fill your hiking quota along a mountain trail in the Berkshires, preferably in the fall as the colors of the leaves change
  • Explore the Boston Museum of Fine Arts, one of the world’s best galleries
  • Take the ferry all the way to Nantucket Island, once the whaling capital of the planet and now one of the world’s most endearing tourist hideaways