2-Hour Boston Segway Tour: Beacon Hill, Cambridge & Freedom Trail

Ride the Longfellow Bridge and loop back through Beacon Hill without walking the whole city

A 2-hour guided Segway tour of Boston that covers downtown, Cambridge and Beacon Hill with an expert guide and all safety gear included. The route crosses the Longfellow Bridge with views of the Boston skyline, passes through the North End and Beacon Hill, and stops at Freedom Trail sites including Boston Common, King's Chapel, Old South Meeting House and the Old Corner Bookstore. You get a private training session before the tour starts and the guide photographs you at key stops along the way.

Step-by-step itinerary

Stops and time spent at each

1. USS Constitution5m
2. Bunker Hill Monument5m
3. TD Garden5m
4. Charles River15m
5. Beacon Hill10m
6. Boston Common10m
7. Old South Meeting House3m

Explore Boston and Cambridge landmarks

• Start at Long Wharf
• Visit Rose Kennedy Greenway
• Pass Christopher Columbus Waterfront Park
• See North End and Paul Revere's Lantern
• Explore Boston’s North End neighborhood
• Visit USS Constitution
• See Bunker Hill Monument
• Learn about Great Molasses Flood
• Pass TD Garden arena
• Enjoy Charles River views
• Cross Longfellow Bridge to Cambridge
• Walk Charles Street in Beacon Hill
• Visit Boston Common park
• See King's Chapel
• Pass Omni Parker House Hotel
• Visit Boston Latin School
• See Old Corner Bookstore
• Visit Old South Meeting House
• Pass Boston Massacre Site

The experience

How much of Boston can you actually see in a morning without spending it on your feet? This tour trades walking for gliding: you start with a private indoor training session to get comfortable on the Segway, then spend two and a half hours covering ground that would take twice as long on foot. The route moves through downtown, crosses the Longfellow Bridge into Cambridge where the Boston skyline opens up across the Charles River, then loops back through Beacon Hill and returns through downtown Boston.

The stops are built around the Freedom Trail but go beyond it. You'll see Boston Common (established 1634, the oldest public park in America), King's Chapel with its Georgian architecture, the Old South Meeting House where thousands gathered to protest the Tea Act, and the Old Corner Bookstore, a 1718 building that once published Hawthorne and Emerson. The route also passes through the North End, Boston's oldest neighborhood, where you'll see Long Wharf (established 1711), the USS Constitution ("Old Ironsides," launched 1797 and still the world's oldest commissioned warship afloat), and the Bunker Hill Monument, a 221-foot granite obelisk marking the first major battle of the American Revolution. Acorn Street, the most photographed street in America, is on the route too.

Your guide is an expert Captain who narrates the history live throughout the tour and carries a walkie-talkie so you can hear over traffic and wind. They photograph you at key stops and you get all the photos afterward. The two and a half hours includes the training session, so the actual riding time is built into that window. You'll need to be at least 14 years old, and the tour isn't recommended for travelers with spinal injuries, pregnancy, or cardiovascular concerns, though it's suitable for all fitness levels otherwise. Public transportation is nearby if you need to get to the meeting point.

What’s included

• All safety equipment including helmet and walkie-talkie.
• private indoor training session before the tour.
• expert guide with live historical narration.
• 2-hour guided Segway tour of downtown Boston, Cambridge and Beacon Hill.
• photos taken by your guide at key stops.

Before you book

Days and timesEvery day7 departure times: the first at 09:00, the last at 15:00

Book up to2h before

AgesAdult (14 and older) · Under 14: can't be booked

GroupUp to 24

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsNo refund if you cancel.

Prices and times updated yesterday

Good to know

Low physical effortPublic transport nearbyNot recommended during pregnancyNot recommended with heart problemsNot recommended with back problems

Operated by Boston Segway Tours

Is this one for you?Two and a half hours is long enough to cover downtown, cross into Cambridge and loop through Beacon Hill without rushing, but short enough to fit into a morning or afternoon without eating the whole day. If you want to see the major Freedom Trail sites and the Charles River views without walking miles, this is the format that makes it possible.

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Top questions

What's the actual riding time if the tour is two and a half hours total?

The two and a half hours includes your private indoor training session before the tour starts, so you're learning to balance and control the Segway first, then riding through the city. The training means you're comfortable before you hit the streets.

Do I need to have ridden a Segway before?

No. Everyone gets a private training session indoors before the tour begins, so you learn the basics in a controlled space before gliding through Boston with your guide.

What Freedom Trail sites does this tour actually stop at?

The 2-hour tour includes Boston Common, King's Chapel, Boston Latin School, the Benjamin Franklin Statue, Old South Meeting House, the New State House, and the Old Corner Bookstore, plus other historic stops like the USS Constitution and Bunker Hill Monument that aren't on the shorter route.

Will I see the Charles River and Cambridge?

Yes. The tour crosses the Longfellow Bridge, which spans the Charles River and connects Boston to Cambridge. That's where you get the full view of the Boston skyline across the water before looping back through Beacon Hill.

What happens if I'm not comfortable on the Segway after training?

The training session is designed to get you steady before the tour starts. If you have concerns about balance, spinal issues, or cardiovascular health, the tour isn't recommended. Talk to the operator before booking.

Are the photos included, or do I pay extra?

Your Captain photographs you at key stops along the route and you receive the photos. It's part of the tour, not an add-on.