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How to Spend 3 Days in Boston

How to Spend 3 Days in Boston

Three days in Boston gives you time to explore the history-steeped city and get out into the surrounding countryside. Uncover the sites behind the American Revolution, tap into Bostonians’ passion for food and baseball, and make time to visit New England’s coastal towns. Here’s how to get the best from a 3-day break in Boston.

Day 1: Dive into the Sights

Kick-start your stay by visiting Boston must-sees such as Boston Common, Harvard University—the USA’s oldest—and the 1794-built USS Constitution tall ship docked at Charleston Navy Yard. To explore at your own pace, opt for a discount city sightseeing pass or hop-on hop-off trolley tour, or go with a guide on a walking, bike, or Segway tour. Next, focus on one of Boston’s claims to fame—its food—on a tour. Explore Little Italy and its pizzerias on a guided walk around the North End district, or take your taste buds around some of Boston’s famously good chocolate shops. In the evening, join a brewpub tour to discover some local craft beers before dinner at a gastropub. Or end the day on a creepy note with a ghost walking tour that delves into the city’s darkest corners and tales.

Day 2: Head Out of the City

Devote today to a day trip—many of New England’s historical towns are within easy reach. Admire the gingerbread cottages and beaches of Martha’s Vineyard, or cast your net further along New England’s coast with a coach tour to places such as Kennebunkport and Cape Neddick Lighthouse. Another destination is Salem, the scene of notorious witch trials of 1692 and 1693. Group and private tours leave from Boston in the mornings and include visits to witch museums and cemeteries.

Day 3: Colonial History to Sunset Cruises

Trace the steps of America’s revolutionaries with a guided walk or drive along Boston’s Freedom Trail—a route studded with colonial-era buildings such as Paul Revere’s House. Perhaps combine it with a stroll around the elegant Beacon Hill and Copley Square neighborhoods; or discover Boston’s baseball heritage by exploring Fenway Park, one of the country’s oldest stadiums. Alternatively, see the wilder side of Boston on a seasonal whale-watching cruise—sailing to Massachusetts Bay to view the mammals in their natural habitat. Spend your last evening on a Boston harbor cruise. Typical options include cocktail cruises or boat trips with dinner and entertainment.

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9 Tours and Activities

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Martha's Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option
Likely to Sell OutLikely to Sell Out

Martha's Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

star-4.5
1273
Join Boston's only award-winning, original, Martha's Vineyard Day Trip! Leave the trouble of driving to someone else and enjoy a day trip to Martha’s Vineyard from Boston. Then, take a short cruise to Martha's Vineyard then enjoy free time to explore or upgrade to add an island tour. Complimentary snacks, bottled water, island guidebooks and a discount card with island perks are provided during the drive.
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  • 12 hours
  • Free Cancellation
From
US$110.00
From
US$110.00

Boston Hop-On Hop-Off Trolley Tour with 14 Stops

Boston Hop-On Hop-Off Trolley Tour with 14 Stops

star-4.5
2411
Explore the best that Boston has to offer on this hop-on hop-off tour of the city. See Boston’s top attractions—like the USS ‘Constitution’ and the Boston Tea Party Ships and Museum, to name a few—on the loop. Enjoy discounted admission to attractions like the Boston Tea Party Ships and Museum with the purchase of your tour.
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  • 1 hour 45 minutes
  • Free Cancellation
From
US$50.40
From
US$50.40

Boston Whale Watching Cruise by High-Speed Catamaran

Boston Whale Watching Cruise by High-Speed Catamaran

star-4.5
1452
Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed catamaran that gets to and from the whales in the least amount of time possible. See humpback and fin whales, plus Atlantic white-sided dolphins with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.
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  • 3 hours 30 minutes
From
US$71.50
From
US$71.50

Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

star-4.5
968
Revel in the history of Fenway Park, one of baseball’s most beloved stadiums, during this guided tour. Revisit the careers of Red Sox greats like Ted Williams, Babe Ruth, and Carl Yastrzemski, celebrate the club’s numerous World Series titles, and tour famous stadium locales like the ‘Green Monster,’ ‘Pesky’s Pole,’ and the Fenway Park Living Museum.
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  • 1 hour
From
US$33.34
From
US$33.34

Boston Premier Odyssey Dinner Cruise
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Boston Premier Odyssey Dinner Cruise

star-4
69
Try a unique alternative to a typical night out in downtown Boston with an exciting dinner cruise along the city’s waterfront. This 2-hour expedition on Boston Harbor features a three-course meal with live entertainment and dancing. Watch the sun set, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night or head to the dance floor for music and fun in the ship’s nightclub. Bring that special someone or a whole group of friends for a night to remember.
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  • 2 hours
From
US$186.99
From
US$186.99

Go City: Boston All-Inclusive Pass with 40+ Attractions and Tours

Go City: Boston All-Inclusive Pass with 40+ Attractions and Tours

star-4
200
Seeing the best of Boston doesn’t get any easier, or more economical, than with Go City's Boston All-Inclusive Pass. This flexible sightseeing pass allows visitors to pick and choose from a wide variety of Boston’s top attractions, over 40 in all, at any pace desired over the course of one, two, three, five, or seven consecutive days. Enjoy immediate entry to attractions. Simply save the pass (available as your 'ticket' after purchase) on your mobile device and go. No voucher redemption is required. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for the remaining number of days purchased.
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  • 1 to 7 days
From
US$62.00
From
US$62.00

Boston City View Bicycle Tour by Urban AdvenTours

Boston City View Bicycle Tour by Urban AdvenTours

star-5
378
Discover Boston’s top attractions on this comprehensive guided bike tour around the city. See the unique character and charm of each community up close, like the beautiful brownstones in Back Bay and the South End. Visit Boston’s historic North End and pedal past Copley Square and Fenway Park. Cross the Freedom Trail, passing significant locations to United States history.
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  • 2 hours 30 minutes
From
US$68.00
From
US$68.00

Boston Guided Brewery Tour with Tastings & Lunch or Dinner
Likely to Sell OutLikely to Sell Out

Boston Guided Brewery Tour with Tastings & Lunch or Dinner

star-5
232
Learn about Boston’s thriving craft beer scene and sample a variety of libations on this morning or evening brewery tour. Get an inside look at how beer is made and learn about their operations as you visit breweries, cider houses, and distilleries. Visit brewpubs that may include the well-known Samuel Adams or gastropub Meadhall. Round-trip transportation in downtown Boston by air-conditioned van is included.
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  • 5 hours
  • Free Cancellation
From
US$115.00
Price varies by group size
From
US$115.00
Price varies by group size

Guided Walking Tour of Copley Square to Downtown Boston Freedom Trail
Likely to Sell OutLikely to Sell Out

Guided Walking Tour of Copley Square to Downtown Boston Freedom Trail

star-4.5
34
Explore elegant neighborhoods, historic streets, and American landmarks on a Boston walking tour from the Back Bay to Beacon Hill and downtown portions of the Freedom Trail. Learn about Boston’s history and culture as you stroll brownstone-lined avenues and walk the shady paths of the Boston Public Garden. Step into Boston’s Revolutionary history in the churches, cemeteries, and battlegrounds of the American struggle for independence.
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  • 2 hours
  • Free Cancellation
From
US$45.00
From
US$45.00