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How to Spend 2 Days in Boston

How to Spend 2 Days in Boston

With two days in Boston, you have time for both a generous dose of American revolutionary history and to explore its more modern side. From charting the origins of US independence on its historical Freedom Trail to taking a whale-watching cruise, here are some ways to spend a perfect 48 hours in the city.

Day 1: Exploring the City

Morning: Boston has plenty to fill your first morning. Follow the Freedom Trail to sites including Faneuil Hall and the 18th-century USS Constitution warship, or explore Harvard University or the city’s museums. Walking and bike tours cover the top sights, or buy a discount sightseeing pass or hop-on hop-off ticket for more flexibility.

Afternoon: After a morning of sightseeing, dial up the adventure for the afternoon. Splash down into the waters of the Charles River on a Boston Duck amphibious tour, or if it’s whale-watching season (generally April-October), take to a high-speed catamaran to see whales in nearby Massachusetts Bay.

Night: Revolutionary history infuses every corner of Boston, making it especially atmospheric after dark. Explore the city’s secret lanes and spooky legends on a ghost-themed evening tour. Options include guided walks into Boston’s oldest lamp-lit districts and a trolley tour that takes you to the city’s haunted buildings and half-forgotten graveyards.

Day 2: Freedom and Food Trails

Morning: Delve into Boston’s revolutionary war heritage on its Freedom Trail. Take a walking tour along the redbrick trail to learn about its British colonial and patriot past, or see the sights from a private car. Finish at the Tea Party Ships and Museum in Boston Harbor to learn more about the war-sparking protests.

Afternoon: See a different side of the city on a tour of some of Boston’s culinary hot spots. Join a guided food walk around the city’s North End district—aka “Little Italy”— to taste its pizzas. Alternatively, opt for a tour of Beacon Hill to discover off-the-beaten path eateries and treats that many miss.

Night: At dusk, take a harbor cruise to relax after your sightseeing and watch the sunset from the water. Choose an all-singing, all-dancing boat with a dinner buffet and live entertainment, or opt for a mellower cruise that settles for serving up sundowner cocktails alongside the city views.

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8 Tours and Activities

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Boston Hop-On Hop-Off Trolley Tour with 15 Stops

Boston Hop-On Hop-Off Trolley Tour with 15 Stops

star-4.5
2024
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. If you upgrade to the Gold or Platinum Pass, you will be given your (seasonal) Harbor Cruise ticket when you check in for the Trolley Tour. These seasonal cruises depart periodically throughout the day close to Stop 1.
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  • 1 hour 45 minutes
  • Free Cancellation
From
$49.35
From
$49.35

Boston Whale Watching Cruise by High-Speed Catamaran
Likely to Sell OutLikely to Sell Out

Boston Whale Watching Cruise by High-Speed Catamaran

star-4.5
1350
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
$62.85
From
$62.85

Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River

Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River

star-4.5
6662
Hop into a duck boat—renovated World War II amphibious vehicle—for a comprehensive tour of Boston. Pass Boston Common, Quincy Market, and the Celtics' home turf at TD Garden. Then splashdown into the Charles River for a view of the city by boat. Learn all about Boston's history and landmarks as you go.
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  • 1 hour 20 minutes
  • Free Cancellation
From
$53.35
From
$53.35

Walking Tour: Downtown Freedom Trail plus Beacon Hill to Copley Square/Back Bay
Likely to Sell OutLikely to Sell Out

Walking Tour: Downtown Freedom Trail plus Beacon Hill to Copley Square/Back Bay

star-4.5
237
Travel back in time through the early years of American history during this guided walking tour of Boston’s famous Freedom Trail and its most iconic landmarks. Relive the events of the American Revolution as you pass Faneuil Hall, see the Old and New State Houses, and visit the setting of the infamous Boston Massacre. Then head downtown past Boston Common and the modern John Hancock Tower, finishing in Copley Square. A professional guide joins your trip to help add context.
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  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

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

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

star-4
185
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
$76.00
From
$76.00

Boston City view Bicycle Tour

Boston City view Bicycle Tour

star-5
353
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
$68.00
From
$68.00

Boston Ghosts & Gravestones Night-Time Trolley Tour

Boston Ghosts & Gravestones Night-Time Trolley Tour

star-4.5
507
Discover some of Boston’s deepest, darkest secrets on a “frightseeing” tour aboard the Trolley of the Doomed, which roams around the haunted streets and burial grounds of Boston. Your costumed host provides illuminating insights into the history of the city's spookiest sights such as Copp's Hill Burying Ground.
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  • 2 hours
  • Free Cancellation
From
$45.15
From
$45.15

Boston Sunset Dinner Cruise with Buffet

Boston Sunset Dinner Cruise with Buffet

star-4
120
Try a unique alternative to a typical night out in downtown Boston on an exciting dinner cruise along the city’s waterfront. This expedition on Boston Harbor features an all-you-can-eat buffet meal with live entertainment and dancing. Watch the sunset, 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 inside 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 30 minutes
From
$104.67
From
$104.67