Private Walking Tour of Freedom Trail and Little Italy
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Walking Tour of Freedom Trail and Little Italy worth booking?
Private Walking Tour of Freedom Trail and Little Italy is a 4.5-hour experience in Boston, United States, from $294 per person. It scores 53 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 53 / 100
- Rating
- 5/5 (6)
- Duration
- 4.5 hours
- From
- $294 per person
See every site on the Freedom Trail! This walking tour includes all 16 stops on the Freedom Trail, covering historical sites such as the Paul Revere House, Copp's Hill Burying Ground, Old North Church, USS Constitution,
What you get
About this experience
See every site on the Freedom Trail! This walking tour includes all 16 stops on the Freedom Trail, covering historical sites such as the Paul Revere House, Copp's Hill Burying Ground, Old North Church, USS Constitution, Boston Common, Old South Meeting House, Old State House, Bunker Hill Monument and more! Listen to hilarious stories from Boston's past as you learn about the history of the area from a longtime resident, passionate historian, and former city employee. Tour includes a short walk through historic Little Italy.
What's included
Included
- Professional Tour Guide
Not included
- Gratuities
- Bottled water
- Lunch
What you'll see and do
Boston Common
Start the day in Boston Common, the oldest public park in the country. Listen to lesser-known stories told by the forgotten plaques and monuments of as you stroll this beautiful park.
25 minutes here
Beacon Hill
Tour Boston’s most prestigious brownstone-lined neighborhood. Visit the “Most Photographed Street in North America”, featuring some of the original cobblestone. Stop by Louisburg Square, previously home to famous writers, today home to famous bankers and politicians.
25 minutes here
Massachusetts State House
Learn about the architecture and history of this famous building. Why is there a pine cone on top of the state house dome? What were the "King's Pines" and why did the pine tree end up symbolizing the American revolution?
20 minutes here
Granary Burying Ground
Visit one of America's most historic cemeteries. Listen to stories of the American Revolution as you visit the graves of famous Founding Fathers Sam Adams, Paul Revere, John Hancock, and more
20 minutes here
King's Chapel Burying Ground
Visit Boston's oldest cemetery, home to the graves of John Winthrop and William Dawes. Hear about King's Chapel, Boston's first Anglican Church, which was deeply despised by the local Puritans.
15 minutes here
Old Corner Bookstore
Visit the site of the Old Corner Bookstore, one of the most prolific publishing houses in early America. This building was where the first run of several important works was released, including Walden, The Scarlet Letter, Battle Hymn of the Republic, and Midnight Ride of Paul Revere.
15 minutes here
Old South Meeting House
View the building where the Boston Tea Party started. Listen to the story of one of Colonial America's most famous rebellions. Hear how Sam Adams rallied the crowd to storm the ships in Boston Harbor and dump the tea in the water.
10 minutes here
Faneuil Hall Marketplace
Learn about the "Cradle of Liberty," where Sam Adams gave his famous speeches that united Boston against the British. Learn about the quirky history behind this building's financial sponsor, Peter Faneuil.
25 minutes here
The Paul Revere House
See the oldest wooden building in downtown Boston, where Paul Revere lived for 20 years. Located on North Square, one of the oldest continually-inhabited areas of Boston, and former home to dignitaries such as Rose Fitzgerald Kennedy.
25 minutes here
North Square Park
Learn about the immigrant past of Boston's North End through public artwork installed on North Square
20 minutes here
Old North Church & Historic Site
See the Old North Church and learn all about the midnight ride of Paul Revere and the historical inaccuracies of the famous poem!
25 minutes here
Copp's Hill Burying Ground
Visit Boston’s second oldest burying ground, taking in view of the harbor and Charlestown, as well as the USS Constitution and Bunker Hill Monument. Learn all about Boston’s part in the events of the American Revolution.
25 minutes here
Visit the historic outlook, where you can see Bunker Hill, the Charlestown Naval Yard, and the site of the Great Molasses Flood
20 minutes here
Where it starts and ends
Meeting point
Boston
Look for the Boston Common Visitors Center located in the Boston Common part. Address is 139 Tremont St, Boston, MA 02111 .
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Copp's Hill Terrace is located in the North End neighborhood, with easy transportation options back to your hotel. Terrace is located at 520 Commercial Street, Boston, MA 02109.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Boston Hidden Gems
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Travelers should have at least a moderate level of physical fitness
Photos
What travelers are saying
Outty’s summary of the themes that recur across 5 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
3 mentionsTravelers single out the guide as the reason the experience works.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Organization
1 mentionPickup, timing, and logistics are described as running smoothly.
Good for families
1 mentionReviewers traveling with kids report it landed well with their group.
Traveler reviews
5 verified traveler reviews for Private Walking Tour of Freedom Trail and Little Italy. Ratings and reviews provided by Viator and Tripadvisor.
Amazing FreedomTrail July Tour
We had the pleasure of touring Boston’s Freedom Trail with BJ from Hidden Gem Tours on Saturday, July 25, as a private family of four. From the moment we met him, BJ was incredibly kind, accommodating, and attentive to everyone in our family. He immediately made us feel comfortable, and it truly felt as though we were exploring Boston with a knowledgeable friend. BJ provided an amazing blend of Boston and Revolutionary War history while keeping the tour engaging and enjoyable for all ages. We especially loved the fascinating extra tidbits he shared about Boston and Massachusetts sports, film locations, and movie history. His warmth, knowledge, and storytelling made this one of the highlights of our trip. We highly recommend BJ and would take another one of his tours again in a heartbeat!
Response from the operator: Thank you for your wonderful feedback! We're thrilled that BJ made your tour memorable with his expertise and storytelling. We’d love to welcome you back for another tour!
via Tripadvisor
Walked the Freedom Trail from Haymarket to Boston Common
We had such a great experience. What a wonderful way to connect with history. Our tour guide, Rocky, was just the best!
Response from the operator: Thank you for sharing your wonderful experience on the Freedom Trail. We're delighted you enjoyed the tour and found Rocky to be exceptional. Hope you make more history-filled journeys!
via Tripadvisor
Amazing historic private walking tour of the Freedom Trail.
Jenny Zipursky was an amazing tour guide. We truly enjoyed our walk around Boston. I learned so much and love the historic city. Would definitely recommend this tour to all my friends.
Response from the operator: Thank you for sharing your enjoyable experience and kind words about the tour! We're thrilled you had such a wonderful time exploring Boston's history with Jenny.
via Tripadvisor
Excellent Day in Boston
Alex met us right on time. After greeting our tour began with an interesting and detailed review of the history of the Boston Common. Alex did an excellent job weaving the story of the revolution into our walking tour. We truly enjoyed this tour and were fortunate to have Alex as our guide.
Response from the operator: Thanks for your review! We're glad to hear you had a great tour of the Freedom Trail with Alex!
via Tripadvisor
Great Tour
Jenny was very friendly, knowledgeable, and loved her job. She was also curious to learn more. She is great.
Response from the operator: We're glad to hear you had a great Freedom Trail & Little Italy tour with Jenny!
via Viator
Good to know
- Duration
- 4.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $294 to $789
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 2
- Verdict
- Worth a Look
Why this scores 53
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Walking Tour of Freedom Trail and Little Italy: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Boston.
How much does Private Walking Tour of Freedom Trail and Little Italy cost?
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Prices start at $294 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Boston usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Walking Tour of Freedom Trail and Little Italy take?
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Plan for about 4.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Boston is not rushed.
Is Private Walking Tour of Freedom Trail and Little Italy worth it?
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It holds an Outty Ranking of 53 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 6 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Boston, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Walking Tour of Freedom Trail and Little Italy?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Walking Tour of Freedom Trail and Little Italy suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 4.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Walking Tour of Freedom Trail and Little Italy?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Boston can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Boston and add a light layer if any part of the 4.5-hour experience runs outdoors or after sunset.
Where does Private Walking Tour of Freedom Trail and Little Italy start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Boston within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Boston?
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Boston is compact enough that a good walking guide beats any bus. Freedom Trail walks, harbour cruises, Fenway tours and whale-watch runs out to Stellwagen Bank are the core, plus Salem and Cape Cod as day trips. Outty Ranking weights guide storytelling and group size heavily, because on the Freedom Trail the narration is the entire product. On Outty we rank every Boston experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Full Revolutionary Story Epic Small-Group Boston Walking Tour, Boston: Freedom Trail History Small Group Walking Tour, Boston's Freedom Trail: A Revolutionary Walking Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Boston?
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May to October. Whale watching runs roughly April through October only. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Boston?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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