13 History Tours in Boston That Repay the Ticket

1.Freedom Trail History Small Group Walking Tour

★★★★★★★★★★5.0 · 6,450 reviews · 2 hours 30 minutes (approx.) · from $35Our pick

Follow Boston’s 2.5-mile Freedom Trail from Boston Common to Copp’s Hill Terrace in a group of no more than 16. Guides such as Jon, Maura, Mark, and Alejandro explain the years leading to the Revolution, answer questions, and add stories at landmarks including Faneuil Hall, Paul Revere’s house, and the Boston Massacre site.

“Jon was very knowledgeable and excited about his subject. It was clear that he had a love for his job, which made it an enjoyable experience.”

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2.Tour of Historic Fenway Park, America’s Most Beloved Ballpark

★★★★★★★★★★4.5 · 3,013 reviews · 1 hour (approx.) · from $45

Spend about an hour inside Fenway Park with a professional guide such as Steve, Matt, Jack, or Mary Ella. See the Green Monster, Pesky’s Pole, roof deck, press areas, and Living Museum, with access to rare Red Sox artifacts. Spanish and Japanese tours can be arranged in advance.

“Totally worth time and cost. We learned about the sox, Boston, Baseball and Fenway. We sat on the green monster and wanted to sit there the next day to watch a game but my husband is a “don’t change the schedule guy”. If I had to criticize I would want more Boston accents! I live in the south and that accent just makes me happy hearing that familiarity is soothing.”

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3.Boston Food & History: Pizza, North End & Freedom Trail

★★★★★★★★★★5.0 · 1,772 reviews · 5 hours (approx.) · from $90

Spend about five hours walking from Boston Harbor through the North End and along the Freedom Trail. Expect bread, pizza, an Italian deli sandwich, coffee and a pastry, plus stories of Paul Revere, the Boston Massacre and the Tea Party. Groups are capped at 12, and guides such as Lexie, Bob, Claire and Nabil bring local character to the route.

“Lexie made the tours fun, informative and so enjoyable. We had our 7 year old with us and she went out of her way to make sure he was having fun. Would definitely schedule with her and Viator again. The food on the tour was great and all the stops were amazing.”

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4.City Cruises Historical Sightseeing Cruise

★★★★★★★★★★4.6 · 1,771 reviews · 1 hour · from $46

Cruise Boston Harbor from Long Wharf for one hour, passing the USS Constitution, Bunker Hill Monument, Old North Church, Castle Island, and the Harbor Islands. English-speaking guides such as Kevin, Holly, Liz, and Dave bring local history to life. Choose the open deck or large-windowed indoor seating, with snacks and drinks available to buy.

“While in Boston we walked all over there for 4 days and saw everything we wanted to see. Hop on hop off was great. Loved the Freedom trail!”

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5.Freedom Trail History Small Group Walking Tour

★★★★★★★★★★4.9 · 1,590 reviews · 2h 30m · from $35

Follow Boston’s Freedom Trail for 2.5 hours with a guide such as Maura, Nick, or Alejandro. You’ll see all 16 official landmarks, from Boston Common and Granary Burying Ground to Paul Revere’s home and Old North Church, with a short break at Quincy Market. The tour ends at Copp’s Hill Terrace with views toward USS Constitution and Bunker Hill.

“I loved all of the stories. I am still telling my wife stories I learned during the tour more than a week later. the guide was excellent.”

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6.City Cruises Boston Historic Sightseeing Harbor Cruise

★★★★★★★★★★4.5 · 1,388 reviews · 1 hour (approx.) · from $46

Take a one-hour narrated cruise from Boston’s Long Wharf past Fort Independence, the USS Constitution, Bunker Hill, Old North Church, Boston Tea Party ships, and Boston Light. Guides such as Kevin, Holly, and Mike bring the harbor’s history to life. Choose the upper deck for the clearest views, or stay inside in cold or wet weather.

“This activity was a lot of fun, even rain or sun. There a lot of things to learn from the guide. He was really funny. It was a fun activity overall”

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7.Boston’s North End Food Tour: Italian Flavors & Heritage Walk

★★★★★★★★★★5.0 · 1,322 reviews · 2 hours (approx.) · from $70

Walk about 1.3 miles from the Greenway Carousel into Boston’s North End, stopping for warm bread, salumi, pizza, pastry, and coffee. Your English-speaking guide, possibly Lexie, Nabil, Bob, or another local host, also covers Paul Revere and Old North Church. The group is limited to 12 people.

“Bob was very accommodating and interactive even with elementary age children! He was able to adjust the orders without sacrificing the quality of the food and gave historical tid bits along the way”

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8.Boston Pizza Lovers Food and History Walking Food Tour

★★★★★★★★★★4.5 · 1,082 reviews · 2 hours 50 minutes (approx.) · from $69

Meet at Modern Pastry for a nearly three-hour walk through Boston’s North End, combining three full pizza slices with five Freedom Trail sights. Guides such as Scotty and Big Al add local stories and humor. The tour ends with a cannoli, and the group is limited to 12 people.

“Pizza tour was great, only problem was that it was so cold out that day. But the tour itself was interesting and the food was good.”

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9.Delicious Donuts of Boston: A Sweet History Walking Tour

★★★★★★★★★★5.0 · 1,038 reviews · 2 hours (approx.) · from $70

Walk through Boston’s Financial District, Public Market, Greenway, Quincy Market, and North End while sampling donuts from Kane’s, Union Square Donuts, Bova’s Bakery, and a local cider maker. Guides such as Jackie, Lucy, Katie, Stephanie, and Izzy mix donut lore with Boston stories. Expect about two hours and more than two miles on foot.

“This was a very cool tour! Yes, the donuts were indeed delicious, however, the tour guide brought Boston’s history alive. Jackie was the best tour guide I have ever seen. She is fun and vibrant. Viator should never lose her. She could guide any tour and make it extraordinary! Thanks Jackie!🩷 Melissa”

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10.Boston Freedom Trail History Pub Crawl Small-Group Tour

★★★★★★★★★★5.0 · 996 reviews · 2 hours 15 minutes (approx.) · from $60

Meet your Boston guide at the Samuel Adams statue by Faneuil Hall for a 2-hour-15-minute pub crawl through four nearby bars. Guides such as Julie, Maddie, Anna, Sam, and Arielle mix colonial and Revolutionary-era stories with local beer suggestions. Drinks cost extra, walking is short, and groups are capped at 12.

“We had a very lovely and entertaining tour guide. She told us loads of Bostons history and shuffled us to four different pubs, all very close together, so not a lot of walking was required.”

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11.Boston City View Bicycle Tour: History and Landmarks

★★★★★★★★★★5.0 · 638 reviews · 2 hours 30 minutes (approx.) · from $78

Ride through six Boston neighborhoods with Urban AdvenTours, covering Fenway Park, the North End, Beacon Hill, Copley Square, and the Charles River Esplanade. Expect about 8 to 11 miles, several short stops, city traffic, and lively local stories from guides such as Gary, Costa, Austin, and Charles. Comfort bikes and pedal-assist e-bikes are available.

“Great way to see and get oriented to the city for first timers. Bikes are in very good condition and the guides shared useful information.”

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12.Boston History Tour: Scenic Walk Through Time & Landmarks

★★★★★★★★★★5.0 · 627 reviews · 2 hours (approx.) · from $39

Join a small group for a 2-hour, 4-kilometer walk from the Greenway Carousel to the Public Garden. Along the way, guides such as Bob, Nabil, Lexie, and Tim bring Faneuil Hall, the Old State House, Boston Common, Beacon Hill, and other landmarks to life with stories, local tips, and a surprise treat.

“We had hoped for a lot more . Seemed like a waste of time walking inside packed shopping retail areas vs spending more time learning more about the history of the area . Not worth the 98.00 per person .”

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13.Boston’s North End Food and History Walking Tour

★★★★★★★★★★5.0 · 459 reviews · 3 hours (approx.)

Spend about three hours exploring Boston’s North End with a local guide, often Paula, whose tour blends neighborhood history with Italian food and wine. Visit an Italian market, bakery, café, liquor shop, and restaurant, with tastings ranging from arancini and prosciutto to cannoli, gelato, espresso, and a two-course lunch.

“So much interesting history in the North End, and the little hidden spots for delicious Italian treats!! Paula is a long time resident of the North End and it is very apparent that she loves it!! She, herself, is a treasure!!”

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