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Discover Boston on a 2-hour Segway tour that covers historic sites, the skyline, and landmark neighborhoods – a fun, efficient way to see the city.
If you’re looking for a way to see Boston that’s both active and informative, a 2-hour Segway tour might just be your ideal choice. This guided adventure offers a fun and efficient way to cover a lot of ground without the fatigue of walking, all while soaking in the city’s sights and stories. While some travelers rave about the knowledgeable guides and breathtaking views, others note that the experience can be a bit physically demanding for some. But overall, it’s a lively, engaging introduction to Boston’s most iconic landmarks.
What we love about this tour? First, the combination of scenic views, especially of the Boston skyline and Charles River, makes it a memorable ride. Second, the comprehensive itinerary that includes not only the historic sites but also modern neighborhoods and hidden gems gives a well-rounded perspective of the city. On the flip side, we’re mindful that riding a Segway can be tricky for those with back or leg issues, and the guided pace might feel rushed to some. This tour suits travelers who want a mix of fun, history, and city vibe in a short amount of time.


This tour promises to give you a thorough taste of Boston’s past and present. From the very start, it begins at 199 State St, right in the heart of downtown Boston. Booking is straightforward, and most travelers find the group size manageable—limited to 24 participants—which helps maintain a personal feel.
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The journey kicks off at Long Wharf, Boston’s oldest pier, established in 1711, and historically a bustling hub for maritime trade. This location sets the tone for the tour — a blend of history and lively city life. You’ll glide past the waterfront, soaking in the views of ships, historic buildings, and the nearby Boston Tea Party ships.
Next, your guide will lead you through the Rose Kennedy Greenway, a modern, lively park that cuts through downtown Boston. This mile-long stretch features food trucks, art installations, fountains, and seasonal events, making it one of the city’s most vibrant spots. As one reviewer pointed out, this is a great place for photos, and the green space offers a welcome break from urban hustle.
The tour then moves into the North End, Boston’s oldest residential neighborhood, famous for its narrow streets and Italian-American culture. Here, you’ll visit Old North Church, where Paul Revere’s midnight ride was signaled by lanterns—an iconic snapshot of American history. Though just a quick stop, the significance of the site is palpable, and many visitors appreciate how the guide contextualizes these landmarks.
Continuing north, you’ll see the USS Constitution at the Charlestown Navy Yard, affectionately called “Old Ironsides”—a symbol of American naval heritage. The Bunker Hill Monument, a 221-foot granite obelisk, commemorates the first major battle of the American Revolution. Both sites are free to view, with just a brief stop for photos and historical tidbits.
A highlight for many is the story of the Great Molasses Flood—a peculiar but tragic event in 1919. Your guide might point out the plaque commemorating this sticky disaster, adding a quirky local flavor. Other stops include the TD Garden, home to Boston’s sports teams, and the Charles River, which offers scenic views of the Boston skyline and Cambridge.
Crossing into Cambridge, you’ll enjoy sights of the Longfellow Bridge with its distinctive salt-and-pepper towers, connecting Boston and Cambridge. Then, a ride through Beacon Hill offers charming brick streets, boutique shops, and timeless Federal architecture—a favorite for photos and strolling.
The tour concludes at the Boston Common, the oldest public park in America, which has served as a gathering place since 1634. Nearby, you’ll see King’s Chapel, Omni Parker House, Boston Latin School, and the Old Corner Bookstore—each with its own story to tell. These sites, though brief stops, deepen your understanding of Boston’s layered history.
Many positive reviews praise the expertise of the guides, with quotes like “Captain J was very informative” and “Rob shared his knowledge freely.” The majority of riders find the Segway manageable, even for beginners, though a few mention it can be taxing on the back and legs, especially if you’re not accustomed to riding.
One traveler noted, “Riding the Segway was easy enough, but it does put stress on your back, legs, feet,” which is worth considering if you have any physical discomfort. The duration of about 2 hours and 30 minutes (including stops and safety briefings) strikes a good balance—long enough to see a lot without feeling rushed.

Price: At $99 per person, this tour offers solid value considering the sights covered and the guided commentary. It’s more than just transportation—it’s a curated experience with historical insights.
Group Size: Limited to 24 people, ensuring a more personalized experience. This smaller group also allows the guide to keep everyone safe and engaged.
Booking and Cancellation: Confirmations are quick, and while the tour is non-refundable, most reviews suggest it’s worth the investment, especially for first-time visitors.
Physical Considerations: Riding a Segway requires a bit of balance and coordination. The experience is suitable for most travelers, but those with back or leg issues may want to consider their comfort.

This tour is ideal for first-time visitors wanting a broad overview of Boston’s landmarks without the fatigue of walking. It suits travelers looking for a fun, interactive way to explore, especially those interested in history, architecture, and scenic views. Families, small groups, and solo travelers alike will find it engaging, especially with guides who are eager to share their local knowledge.
If you’re short on time but want to cover familiar sights efficiently, this tour hits all the highlights. However, for those who prefer a more leisurely, in-depth exploration of each site, a slower walking tour might be more suitable.

A 2-hour Boston Segway tour offers a lively, memorable way to glimpse the city’s most famous landmarks, from historic sites to vibrant neighborhoods and scenic river views. The combination of ease, speed, and insider commentary makes it a great option for travelers eager to see a lot in a short time.
While riding a Segway might not be for everyone—especially if you’re concerned about physical comfort—the overall experience is often described as safe, friendly, and informative. It’s especially perfect for those who want a taste of Boston’s history and modern cityscape without spending hours on foot.
Whether you’re visiting Boston for the first time or looking for a fun activity to break up your sightseeing, this tour delivers entertainment and insight in one compact package. Just remember to wear comfortable shoes and come ready to learn, laugh, and enjoy some of the best views in the city.
“Great tour! Great tour guide! Highly recommended! Beyond expectations for duration, quality, and knowledge.”

Is the tour suitable for beginners?
Yes, most riders find the Segway easy to operate, and guides are there to help you get comfortable before starting.
What is the meeting point?
The tour begins at 199 State St, Boston, MA 02109, located conveniently near public transportation.
How long does the tour last?
The total duration is approximately 2 hours and 30 minutes, including stops and safety instructions.
Can I participate if I have physical issues?
While most can enjoy the tour, those with back, leg, or foot issues should consider their comfort level as riding can put some stress on those areas.
How many people are in a group?
Groups are capped at 24 travelers, fostering a more personal experience.
What landmarks will I see?
Expect to see everything from Long Wharf, Boston Common, the Old North Church, Bunker Hill, the Charles River, Beacon Hill, and much more.
Do I need to book in advance?
Yes, pre-booking is recommended, especially during busy seasons—confirmations are provided immediately upon booking.
Is the tour non-refundable?
Correct, the booking is non-refundable and cannot be changed once confirmed.
What should I wear?
Comfortable, weather-appropriate clothing and closed-toe shoes are recommended, as you’ll be on your Segway for much of the time.
How scenic is the tour?
Very scenic—viewpoints of the Boston skyline, harbor, historic neighborhoods, and the Charles River make for a varied and beautiful experience.
In summary, if you want a lively, guided introduction to Boston that combines fun with education, this 2-hour Segway tour is a smart pick. It offers a balance of history, scenery, and activity—perfect for making the most of a short visit or adding a memorable highlight to your Boston trip.