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  • Boston skyline
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    Boston: A Hub of History, Higher Learning and Winning Sports Teams

  • Plimoth Plantation
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    Plymouth: Colonies and Clam Rolls

  • Life Saving Grace Point in Cape Cod
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    Cape Cod: Summer Like a President

  • Nantucket
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    Nantucket: A Whaling Town Turned Summer Surf Spot

  • Martha's Vineyard coastline
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    Martha’s Vineyard: Cottages, a Carousel and Lobster Rolls

Martha's Vineyard coastline
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Beach-hopping Around Boston

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    1-2 weeks

Come summer, the Massachusetts shore is a wonderful place to be

Quaint beach towns, fresh seafood and sweeping harbor views: A trip to coastal Massachusetts is a dream come summertime. Begin your beach vacation in historic Boston, soaking up American history along the Freedom Trail or from the bleachers of Fenway Park baseball stadium, home of the Boston Red Sox. Then head south to the shores of Plymouth Colony and down the coast to the dune-backed beaches of Cape Cod, island hopping to Nantucket and Martha’s Vineyard, where days revolve around sand, sunsets and scoring the freshest lobster rolls.

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Boston skyline
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Boston: A Hub of History, Higher Learning and Winning Sports Teams

One of America’s oldest cities and the birthplace of the American Revolution, Boston exudes history at every cobblestoned street corner. Lace up your walking shoes and follow the 4-kilometer Freedom Trail from Boston Common, the oldest city park in the U.S., to the 18th-century warship known as the USS Constitution. The bright red line marking the path is easy to follow and passes by 16 historically significant sites along the way.

It’s not all history in Boston: Home to 35 colleges and universities, the city’s intellect runs high. Take the subway (locally known as “the T”) across the Charles River and wander the storied grounds of Harvard University in Cambridge or visit Boston Public Library, an architectural gem in Copley Square that boasts the second-largest volume of books in the country.

Art lovers will want to plan a visit to the Museum of Fine Arts, one of America’s leading art museums with a collection of nearly 450,000 works, or the more intimate Isabella Stewart Gardner Museum, which showcases its founder’s eclectic global collection of furniture, textiles, sculptures and ceramics. From here, it’s an easy walk along the beautiful trails of the Back Bay Fens to the up-and-coming Fenway neighborhood. Whether you’re a sports fan or not, it’s worth walking down Yawkey Way and catching a glimpse of Fenway Park, the oldest baseball stadium in Major League Baseball. Nearby, get a taste of Boston’s dynamite food scene at Southeast Asian-inspired Tiger Mama or Island Creek Oyster Bar.

64 km
1 hour by car
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Plimoth Plantation
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Plymouth: Colonies and Clam Rolls

Continue your history lesson by driving about an hour south along Interstate 93 and Massachusetts Highway 3 to Plymouth, best known for its famous rock, where English “pilgrims” aboard the Mayflower ship landed and set up Plymouth Colony, the second permanent English settlement in North America, in 1620. Nearly 1 million visitors a year travel to the shore of Plymouth Harbor to view this humble symbol of American heritage. But there’s more to see than just a rock. Plimoth Plantation is like a living history museum, where costumed guides lead you through a re-creation of a 17th-century village that includes the homesite of the Wampanoag Indians and a replica of the Mayflower. A bit farther down the road you’ll find the entrance to Plymouth Beach. Sun and swim, then stop by Sandy’s for a clam roll and scallop stuffie.

53 km
0.75 hours by car
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Life Saving Grace Point in Cape Cod
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Cape Cod: Summer Like a President

The Cape, as locals lovingly refer to it, resembles the arm of someone flexing their bicep. Comprising 15 towns, this 124-kilometer-long stretch of sand is one of America’s most popular summer destinations thanks to its laid-back beaches, charming ice cream shops and seafood shacks. Iconic U.S. president John F. Kennedy spent his summers here, and today the Kennedy Compound in Hyannis is still used by the family. Ten minutes from the compound, the John F. Kennedy Hyannis Museum provides an in-depth look at JFK’s time on the Cape.

You’ll have no problem finding your own perfect patch of sand. Chatham Lighthouse Beach is one of the most scenic, while Gray’s Beach in Yarmouth has a wooden boardwalk that winds through a natural salt marsh where you can spot osprey. Scusset Beach State Park welcomes campers, and Skaket Beach in Orleans is where locals head to enjoy the sunset. In the evening, catch a show at the Cape Playhouse, which has been attracting top talent since opening in 1927. At least one meal a day should be eaten in a salt-dog seafood shack. Try the fried lobster tail at Arnold’s Lobster & Clam Bar in Eastham or grab “lobstah” rolls for a beach picnic at Mac’s Chatham Fish & Lobster.

41 km
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Nantucket
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Nantucket: A Whaling Town Turned Summer Surf Spot

From Hyannis, hop a ferry to the tiny island of Nantucket. The 42-kilometer journey, which takes anywhere from 1 hour to 2 hours and 15 minutes, will allow you a glimpse of the Kennedy Compound. Once on the island, head to cobblestoned Main Street, a lively area just off the harbor. Spend some time exploring the shops, like family-run Murray’s Toggery Shop, and be sure to grab a scoop of homemade ice cream at the Juice Bar. Then, get a glimpse of the island’s past at the Whaling Museum. Bring your camera and take a photo of the 14-meter sperm whale skeleton hanging from the ceiling of the whale hunt gallery, then climb the circular staircase to Tucker’s Roofwalk atop the museum to take in panoramic views of the harbor. When you’re ready to play in the waves, head to Cisco Beach, Nantucket’s go-to surf spot. Nantucket Island Surf School, based right in the beach-access parking lot, can help you learn the basics of surfing. After a day of surf and sun, catch the free shuttle bus (departing from the visitor center from noon to 6:30 p.m.) to Cisco Brewers and enjoy a local beer and live music on the weekends.

60 km
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Martha's Vineyard coastline
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Martha’s Vineyard: Cottages, a Carousel and Lobster Rolls

The high-speed inter-island ferry connects to the island known as Martha’s Vineyard in just over an hour. Start your visit in the historic resort community of Oaks Bluff, a popular destination in the 19th century — the canvas tents that hosted visitors back then were eventually replaced by the colorfully painted Carpenter Gothic cottages that remain today. Both adults and kids should take a spin on the Flying Horses Carousel, one of the oldest in America. Afterward, head to the southwestern tip of the island and walk the gray Aquinnah Cliffs, carved by millions of years of glacial erosion. Follow the upper trails so you can catch a view of Gay Head Light and, on a clear day, the Elizabeth Islands. Settle in for sunset at Menemsha Beach, then head into the classic New England fishing village and order a hot buttered lobster roll from Larsen’s Fish Market to enjoy on the waterfront. End your Massachusetts experience back in Boston, just a 2.5-hour trip away.

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Golden Gate Bridge, San Francisco, California
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