3 Days in Boston: Suggested Itineraries

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Freedom’s the word in Boston. From the Boston Tea Party and the Boston Massacre to the beginning of the American Revolution, this city’s steeped in history and lucky for you, it’s one of the few cities in the ‘Land of the Free’ where you can feel free to leave your car at home.

Day 1: Boston Sightseeing

The historic core of Boston begins and radiates outward from Boston Common, and thus it's a great place to orient yourself. Before you get going, though, consider getting a Go Boston Card, which gives you free entry to 70 of Boston's sights, attractions and tours. You can then start your Boston foray by following the Freedom Trail, winding past iconic colonial and Revolutionary sites. Then, to get a more in-depth view of Beantown, jump aboard the Boston Hop-on, Hop-off Trolley Tour - you can hop on and off at any of the 17 centrally located stops as often as you like.

Day 2: Out and About in Boston

From historic walks and ghostly encounters to leisurely cruises by day or night, there are plenty of ways to get out and about in Boston. Explore the exquisite architecture of the city's cosmopolitan Back Bay district or take a guided walk around historic Beacon Hill, an evocative 18th century neighborhood of charming streets, brick sidewalks lined with gas lamps, hidden houses, and parade of doors and doorknockers. For more history, retrace that famous tea party on a walking tour of Boston's waterfront, or meet ghouls and witches on a nocturnal Ghosts and Gravestones walk with a 17th century gravedigger.

Day 3: Day Trips From Boston

Boston is brilliantly positioned for all kinds of day trips, from colonial-era sightseeing to splashing across the water seeking whales, to lounging about in quaint Cape Cod. Start your foray into the Boston area's past with a visit to the historic Plimoth Plantation, a fascinating re-creation of 1620s Plymouth, or relive the 1690s witch trials on a day trip to Salem. Boston's Revolutionary story is complete when you visit Lexington and Concord, and there's more recent history at the fabulously opulent mansions and yachts of wealthy Newport.

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