13 Historical Tours in Boston That Are Worth the Ticket

1.Freedom Trail History Small Group Walking Tour

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

Review of Boston’s 2.5-hour Freedom Trail walking tour, with all 16 landmarks, expert guides, practical tips, price value, and drawbacks.

“Our travel guide Alejandro was knowledgeable and enthusiastic in his depiction of each historical destination. He was sympathetic to the frigid cold temperatures and we had warm-up breaks, which were appreciated. His overall presentation was educational and informative to even the Boston resident!”

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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

Tour historic Fenway Park, sit atop the Green Monster, see Red Sox memorabilia, and learn Boston baseball stories in one hour.

“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

Taste North End bread, pizza, and Italian specialties before walking Boston’s Freedom Trail, Beacon Hill, and harborfront with a local guide.

“Lexie was fun and knowledgeable. We enjoyed the tour. We would highly recommend her! Thanks for a wonderful day.”

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4.City Cruises Historical Sightseeing Cruise

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

See Boston Harbor, USS Constitution, Castle Island, and Revolutionary sites on a lively one-hour cruise with indoor and outdoor seating.

“We had such a great time, our tour director was so informative with such a great personality. He explained in great detail every site that was on the tour. It was so interesting, highly recommend taking this tour.”

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5.Freedom Trail History Small Group Walking Tour

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

Walk Boston’s Freedom Trail in a small group, hearing Revolution-era stories and seeing 16 landmarks for $35.

“I think a way to keep track of the freedom trail things we've seen as we go by would've been good. think like a hit list. there's just so much going on it's easy to get lost in the sauce”

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6.City Cruises Boston Historic Sightseeing Harbor Cruise

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

Review of Boston’s 60-minute historic harbor cruise, with USS Constitution, Boston Light, skyline views, practical tips, and honest value advice.

“The narrator on the boat ( i think his name was Jeff?) was fantastic. He had the girt of gab along with a sense of humor and fullof history and information about Boston as well as the harbor”

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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

Taste bread, pizza, salumi, pastry, and coffee while walking Boston’s North End with a small group and Old North Church visit.

“Skip breakfast, you'll need the room. Coffee and pastry, followed by bread, pizza, and a sandwich. Great food. Our guide, Nabil, knew so much of interest about Boston's North End.”

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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

Taste three Boston pizza slices, a cannoli, and North End history on a small-group Freedom Trail walking tour.

“This tour was wonderful. I went with my family of 6 and we all loved it. We started at a delicious cannoli place and also stopped at 3 pizza places in the North End and had a slice of pizza at each. Each one was different and delicious. Scotty was the tour guide and he was great. Very entertaining and great stories and information about the North End. This is our favorite section of Boston and we enjoyed the tour and all the food. We were stuffed and happy! Take this tour...you won't regret it!”

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

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

Taste Boston’s best donuts while walking from Kane’s to the North End, with local history, cider, coffee, and four bakery stops.

“my coworkers and I had a great time! Lucy was so personable and very knowledgeable/ passionate about donuts!”

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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

Review of Boston’s Freedom Trail pub crawl, with historic stories, four nearby bars, practical tips, costs, and who will enjoy it most.

“Short and enjoyable walk from place to place. Fun information Julie was great. The other members of the group were fun”

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11.Boston City View Bicycle Tour: History and Landmarks

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

Review of Boston’s 2.5-hour City View Bicycle Tour, with route details, landmarks, safety advice, pricing, and who should book.

“What a great way to see the city!! Great tour, great guide! Just be aware that the bikes are pedal-driven. There isn’t a throttle, so you do have to pedal to make the bike go. It’s still very easy, but if go into it thinking you won’t need to pedal, that’s not how it works. Highly recommend.”

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

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

Walk Boston’s historic core from Faneuil Hall to the Public Garden with local stories, a small group, and practical city tips.

“Allison did a great job sharing the history of the area. She answered questions from the group and we could tell she loves her job.”

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

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

Explore Boston’s North End through Italian food, wine, family businesses, and local history on a small-group walking tour with Paula.

“Knowledgeable and fun, learned about north end and Italian culture had great food, perfect portions best cannoli ever!!!”

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