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7-Day Massachusetts Itinerary

A mix of American history, coastal charm, and outdoor adventures across Massachusetts.

The Ultimate Massachusetts Family Vacation: Kid-Friendly History, Coastal Adventures & New England Charm

Day1

Arrive in Boston & Explore the Freedom Trail

Fly into Boston Logan International Airport (BOS).

Top Things to Do in Boston

  • Walk the Freedom TrailVisit 16 historic sites, including Paul Revere's House, Faneuil Hall, and the Old North Church.
  • Tour Fenway ParkHome of the Boston Red Sox (or catch a game if in season!).
  • Visit the Boston Tea Party Ships & MuseumAn interactive look at the Revolution.
  • Dinner at Legal Sea Foods or Union Oyster HouseTry New England clam chowder & lobster roll.

Overnight in Boston.

Day2

Cambridge & Harvard, Boston's Waterfront

Explore more of Boston & the historic town of Cambridge.

Top Things to Do

  • Walk Through Harvard UniversityVisit Harvard Yard & Harvard Square.
  • Explore the Boston Harborwalk & Take a Boston Harbor Cruise.
  • Dine at Neptune OysterOne of the best seafood spots in the city.
  • Walk Across the Charles River EsplanadeBeautiful views at sunset.

Overnight in Boston.

Day3

Plymouth - Where America Began

Drive from Boston to Plymouth (45 minutes).

Top Things to Do in Plymouth

  • See the Mayflower IIA full-scale replica of the ship that carried the Pilgrims.
  • Visit Plimoth Patuxet MuseumsA living history museum recreating the 17th-century colony.
  • Walk Along Plymouth Harbor & See Plymouth Rock.
  • Try Seafood at Wood's Seafood or East Bay Grille.

Overnight in Plymouth or Cape Cod.

Day4

Cape Cod - Beaches & Lighthouses

Drive from Plymouth to Cape Cod (1 hour).

Top Things to Do in Cape Cod

  • Relax on Nauset Beach or Race Point Beach.
  • Explore Chatham's Quaint Downtown & Chatham Lighthouse.
  • Bike Along the Cape Cod Rail Trail.
  • Go Whale Watching in Provincetown (Seasonal: April-October).

Overnight in Provincetown or Chatham.

Day5

Martha's Vineyard or Nantucket Island

Take the Ferry from Cape Cod to Either Martha's Vineyard or Nantucket (1 hour).

Top Things to Do in Martha's Vineyard

  • Visit Oak Bluffs & See the Gingerbread Cottages.
  • Bike to Edgartown & South Beach.
  • Eat Fresh Lobster at Larsen's Fish Market in Menemsha.

Top Things to Do in Nantucket

  • Relax at Cisco Beach.
  • Visit the Whaling Museum.
  • Bike the Scenic Sconset Bluff Walk.

Return to Cape Cod & Drive to Boston (2 hours).

Overnight in Boston.

Day6

The Berkshires - Mountains & Small Towns

Drive from Boston to The Berkshires (2.5 hours).

Top Things to Do in The Berkshires

  • Hike Monument Mountain or Bash Bish Falls State Park.
  • Visit The Norman Rockwell Museum in Stockbridge.
  • Enjoy Wine Tasting at a Local Vineyard.
  • Explore the Clark Art Institute in Williamstown.

Overnight in The Berkshires.

Day7

Return to Boston & Depart

Drive from The Berkshires to Boston (2.5 hours).

Optional Stops Along the Way

  • Visit Walden Pond in ConcordWhere Henry David Thoreau lived.
  • Explore Lexington & ConcordKey sites of the American Revolution.

Fly out of Boston (BOS).

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Header photo: King of Hearts, CC BY-SA 4.0, via Wikimedia Commons.