If you’re looking for a way to see Boston’s highlights with a twist of fun, the 2-hour Boston Segway Tour might just be what you need. This guided adventure promises a thorough overview of the city’s most famous sites, blending history, scenic views, and a bit of modern mobility. Whether you’re a history buff or just want a memorable way to cover more ground than walking, this tour has something to offer.
What we really like about this experience is how it combines ease and excitement. Riding a Segway is surprisingly straightforward, and it opens up the city’s sights from a fresh perspective. Plus, the tour covers a significant chunk of Boston’s historic core and some of its most photogenic spots. The other thing that stands out is the knowledgeable guides, who add context and local color that elevate the experience.
Of course, there are a couple of things to keep in mind. Riding a Segway can be a bit demanding on your legs and back, especially if you’re not used to it. And because the tour is quite comprehensive, it’s definitely suited for those with a sense of adventure and some basic comfort on a Segway. This tour tends to attract those eager to combine sightseeing with a bit of offbeat fun — perfect for active travelers and those who want a quick but meaningful overview of Boston.
Key Points

- Comprehensive route covering iconic landmarks from Boston Common to Cambridge.
- Knowledgeable guides who share engaging historical stories.
- Scenic views of the Boston skyline, Charles River, and historic neighborhoods.
- Accessible for beginners, with safety and instruction included.
- Good value at $99 for 2 hours, considering the coverage and insight.
- Limited group size, ensuring personalized attention.
The Itinerary in Detail

The tour kicks off at 199 State Street, right in the heart of downtown Boston. From there, you’re introduced to the basics of riding a Segway before heading out on a route that hits many of Boston’s most beloved sights. The experience lasts approximately two and a half hours, giving plenty of time to enjoy each stop without feeling rushed.
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Long Wharf and the Rose Fitzgerald Kennedy Greenway
The journey begins at Long Wharf, Boston’s oldest pier established in 1711. Here, you’ll get a sense of the city’s maritime past, with views of the harbor and boats bobbing at dock. Just a short ride away is the Rose Fitzgerald Kennedy Greenway, a lively, mile-long park with gardens, fountains, and art installations. This spot offers a pleasant introduction, with plenty of photo opportunities of the bustling city backdrop.
Christopher Columbus Waterfront Park & North End
Next, the tour moves into the North End, Boston’s oldest residential neighborhood. Here, historic streets and Italian-American culture blend seamlessly. The group then visits Christopher Columbus Waterfront Park, which provides panoramic views of Boston Harbor, a perfect place for a quick stop and some photos.
Historic Landmarks and Revolutionary Sites
The tour covers key sites tied to Boston’s revolutionary past. At Old North Church, famous for Paul Revere’s midnight ride, you’ll learn about its role in colonial rebellion. The stop at the Bunker Hill Monument is a highlight, where a towering granite obelisk commemorates the first major battle of the American Revolution. Nearby, the Great Molasses Flood Plaque tells the story of Boston’s most bizarre industrial disaster in 1919.
The USS Constitution, launched in 1797 and still afloat, offers a glimpse into early American naval history. The TD Garden, home of the Celtics and Bruins, is also visible from the route. Crossing the Charles River on the Longfellow Bridge, you’ll enjoy one of Boston’s most iconic views—perfect for photos and simply soaking in the scenery.
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Beacon Hill and Downtown
The tour continues into Beacon Hill, with its brick-lined streets and Federal-style row houses. Charles Street here is great for window shopping or grabbing a coffee. The Boston Common, established in 1634, is the oldest public park in the U.S. and provides a peaceful break in the midst of the city’s hustle.
Cultural and Historic Stops
Further along, the tour passes King’s Chapel, the Omni Parker House (famous for its Boston Cream Pie), and Boston Latin School, the nation’s oldest public school. The historic Old Corner Bookstore and Old South Meeting House are also on the route, both rich with stories of Boston’s literary and revolutionary past.
The Climax: The Boston Massacre Site
To wrap up, the guide points out the Boston Massacre Site near the Old State House, where tensions between colonists and British soldiers escalated into violence. This stop ties the tour’s broader story of Boston’s role in American independence.
What to Expect
Throughout the tour, you’ll enjoy a balance of riding and stopping. The group sizes are capped at 24, which helps keep the experience intimate and allows guides to give their full attention. According to reviews, most participants find riding a Segway surprisingly easy, even for beginners. Although some mention it can stress your legs and back, the safety instructions and support from the guides help keep this manageable.
The scenic views of downtown Boston, the Charles River, and historic neighborhoods are a big plus. Many reviewers said the guides brought history to life with engaging stories, making the experience both educational and entertaining. One reviewer noted, “Captain J was very informative and always willing to help,” emphasizing the professional yet friendly vibe.
The flexibility of the route, which includes the same landmarks as shorter tours but adds more depth, makes this especially appealing for those wanting to see more than just the basics. The tour’s duration of 2 hours 30 minutes feels just right—long enough to take in sights without fatigue setting in.
The Value and Price

At $99 per person, this tour offers good value, especially considering the coverage and the guided experience. Covering both historic sites and scenic overlooks, it’s a cost-effective way to get a broad overview of Boston. Some reviews point out that the tour provides a fun alternative to walking, allowing you to see more ground with less effort.
It’s worth noting that this is a non-refundable booking, so plan accordingly. The small group size and professional guidance mean you’ll feel safe, even if you’re new to Segways.
Who Will Love This Tour?
This experience is perfect for active travelers who want a dynamic and engaging way to see Boston’s highlights. It’s suitable for beginners, thanks to the thorough instruction and safety precautions. History lovers will appreciate the stories and landmarks, while those after scenic views will find plenty to admire, especially along the Charles River and from the bridge.
Foodies, shoppers, or those with limited time in Boston will find this a practical way to get an overview, especially if walking long distances isn’t appealing. The tour is also ideal for families or groups wanting a shared, fun activity that combines learning with adventure.
The Sum Up

The 2-hour Boston Segway Tour offers a well-rounded experience that balances history, scenic views, and fun. Its knowledgeable guides make the city’s stories come alive, and the coverage of landmarks from Boston Common to Cambridge ensures you leave with a meaningful understanding of Boston’s past and present. The ease of riding a Segway makes it accessible even for beginners, and the small group setting keeps the experience personal and safe.
While it might not be suitable for those with mobility issues or discomfort on a Segway, for most active visitors, this tour provides great value. It’s an excellent choice for first-time visitors wanting a memorable, efficient way to explore Boston’s iconic sights.
FAQs

Is this tour suitable for beginners?
Yes, most travelers find riding a Segway surprisingly easy. The guides provide safety instructions and support to help you get comfortable before heading out.
How long does the tour last?
The tour runs approximately 2 hours and 30 minutes, including riding time and stops at key landmarks.
What landmarks will I see?
You’ll visit sites like Boston Common, King’s Chapel, the Old South Meeting House, USS Constitution, Bunker Hill, Charles River, Beacon Hill, and many more.
Is the tour family-friendly?
Yes, most travelers, including families, enjoy this tour. However, children should be comfortable riding a Segway and able to follow safety instructions.
How much does it cost?
The price is $99 per person, which covers the guided tour, Segway rental, and safety equipment.
What is the group size?
Groups are limited to a maximum of 24 travelers, ensuring a personalized experience.
Are there any physical demands?
While riding a Segway is generally manageable, it can put some stress on your legs and back. It’s best suited for those who are reasonably active.
What should I wear?
Comfortable clothing suitable for outdoor activity is recommended. The guides will provide safety gear, including helmets.
Can I cancel if my plans change?
No, this experience is non-refundable and cannot be changed once booked.
Whether you’re a history enthusiast or just looking for a fun way to see Boston, this Segway tour offers a lively, engaging, and practical way to experience the city. It promises a blend of scenic beauty, historical insight, and a dash of adventure—all led by guides eager to share their love for Boston.
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