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Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Discover Boston with a small-group, customizable tour led by an expert guide, visiting iconic sites like Harvard, Bunker Hill, and the USS Constitution.


This small-group Boston tour, priced at $159 per person, offers an intimate way to see many of the city’s most iconic landmarks. With a maximum of six guests, the experience guarantees personalized attention from the guide, ensuring that your interests shape the day’s activities. The 6 to 7 hours tour is perfect for visitors who want a thorough, relaxed exploration, with the flexibility to skip what doesn’t appeal.
The tour starts at the Boston Marriott Long Wharf and includes hotel pickup, making the start of your day smooth and stress-free. Booking is highly recommended, with most reservations made about 60 days in advance. This tour suits travelers looking for a comprehensive, flexible, and personalized Boston experience, especially those who appreciate in-depth knowledge and custom stops.
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The guide, often described as knowledgeable, personable, and engaging, is what truly sets this tour apart. They go above and beyond to tailor the experience, answering questions and sharing stories that most visitors won’t hear elsewhere. Many reviews highlight the guide’s friendly demeanor, humor, and willingness to spend extra time on particular sites.
This expert storytelling enhances visits to places like Harvard University, where the history of the institution’s growth from a converted home to a world-renowned research university is explained. The guide also shares local anecdotes and little-known facts, making Boston’s history feel closer and more personal.

The first stop on the tour is Harvard University, where a detailed story unfolds about how a modest home with a one-acre barnyard transformed into a globally influential institution. Visitors spend about 30 minutes here, enough to gain a sense of Harvard’s prestige and its historical significance in Boston.
Although no admission fee is charged at Harvard, the tour emphasizes the university’s impact on education and local history. The guide’s insights bring to life the legacy of influential figures associated with Harvard, making it a highlight for those interested in academic history.

Next, the tour visits Bunker Hill, site of the first battle of the Continetal Army. The 30-minute stop offers a vivid recounting of the battle, which was a pyrrhic victory for the British but a crucial lesson for the Patriots.
Visitors get to stand at the battlefield and learn about the significance of the fight in the American Revolution. The guide shares stories of heroism and strategic importance, bringing the battle’s history to life. This stop appeals to those interested in Revolutionary War history and military tactics.

The Charlestown Navy Yard is another key stop, emphasizing America’s naval history. Visitors see where battleships were built and repaired and visit the U.S.S. Constitution, famously known as Old Ironside. This 30-minute visit offers the opportunity to explore the historic ship, which is still afloat today.
Many reviews praise the USS Constitution as outstanding, calling it a highlight of the tour. The naval yard’s history as the home of American battleships adds a military dimension to the Boston story, and the guide’s insights make the visit both educational and inspiring.

The tour includes a short stop at Beacon Hill, the oldest neighborhood in Boston, where the wealthy and influential once ruled. Visitors are encouraged to take pictures and explore on their own for about 10 minutes.
Nearby, the North End, known as Little Italy, offers a glimpse into Boston’s immigrant past, transitioning from British and French Protestant roots to a hub of Irish and Jewish communities. This 10-minute stop provides opportunities for pictures and brief exploration of historic streets.

The Faneuil Hall Marketplace stands out as America’s oldest outdoor market and Boston’s first town hall. Visitors spend around 10 minutes here, soaking in the vibrant atmosphere and learning about its role as a center of commerce and gathering.
Next, the Old State House offers a deep dive into colonial and early American government. It is the scene of the Boston Massacre and the reading of the Declaration of Independence. The site itself is not included in the ticket price but is a significant historical stop.

The tour also visits the Old City Hall, once the location of the Latin School, America’s first public school. Only 10 minutes are allocated here, with free access to the street outside.
King’s Chapel, the oldest burial ground in Boston, offers a serene, historic setting. Visitors can walk through, with 10-minute stops at each site, gaining insight into Boston’s religious history and early community life.
The Granary Burying Ground is the final resting place of many patriot leaders, built on the site of a grain house due to space limitations. This 10-minute stop highlights patriot burials and early Boston life.
The Old South Meeting House served as a meeting place for Liberty protests and is known for its role in colonial resistance. Although admission is not included, it remains a symbol of revolutionary activism. The 10-minute stop offers a glimpse into the early fight for independence.
The tour begins at 9:00 am at the Boston Marriott Long Wharf and ends back at the same location. The vehicle used is an SUV, which comfortably accommodates up to six guests. The guide provides bottled water, soft drinks, or juice throughout the day.
The tour is designed for guests with moderate physical fitness, with several stops for walking and brief exploration. The pickup service adds convenience, making the experience accessible even for those unfamiliar with Boston’s layout.
A key feature of this tour is its customizability. Stops can be added or skipped based on guest preferences. The guide is willing to stop on request for photos or extra exploration, making this a tailored experience that aligns with individual interests.
While the tour lasts around 6 to 7 hours, the pacing is steady, with enough time at each site to enjoy without feeling rushed. Many reviews emphasize how the guide goes out of their way to make the day personal and enjoyable.
With a perfect 5.0 rating based on 42 reviews and a 97.6% recommendation rate, this tour has established a reputation for quality and personalized service. Review details consistently praise knowledgeable guides, comfortable rides, and the ability to see more of Boston than expected.
While luggage handling was cited as a minor issue in one review, the guide responded proactively, hiring taxis and offering a refund. The value for money and attention to detail make this a highly recommended choice for those seeking a focused, flexible Boston tour.
This small-group, customizable tour is ideal for history enthusiasts, first-time visitors, or anyone wanting a personalized, relaxed exploration of Boston. It suits those who value knowledgeable guides and flexible schedules over large, impersonal bus tours. Given its limited size, it offers a level of comfort and engagement not found in bigger groups.
The Small Group Boston Tour offers an intimate, informative, and flexible way to explore the city’s most famous landmarks and hidden sites. The expert guide, combined with a tailored itinerary and small group size, ensures guests get personalized attention and deep insights into Boston’s history.
While the luggage handling might be a challenge in some cases, the guide’s proactive response and service extras help mitigate this. This tour is most suited for guests who want a comprehensive, engaging day with plenty of opportunities for questions and custom stops. For those seeking a memorable, curated experience of Boston, this tour delivers on all fronts.
“Great, personalized experience! Stewie listened to what we wanted from the experience and got to see so much of Boston.”
Is hotel pickup included?
Yes, the tour offers hotel pickup at the Boston Marriott Long Wharf, making it convenient to start your day.
What is the maximum group size?
The tour is limited to six guests, ensuring personalized attention from the guide.
How long is the tour?
The tour lasts approximately 6 to 7 hours, providing ample time to see all the key sites and enjoy in-depth explanations.
Can I customize the stops?
Yes, the tour is customizable. Stops can be added on request, and the guide is happy to accommodate special interests.
What should I bring?
Comfortable shoes are recommended. The guide provides bottled water and drinks throughout the day. The tour is suitable for those with moderate physical fitness.