Driving in Boston is not for the faint of heart. More than 50% of the streets in the historic areas are nearly 400 years old, built at the end of the late Middle Ages as winding pedestrian or bovine walkways. They are narrow, winding, often hilly, and mostly one-way streets. There is a lot of charm in Boston, but you may find yourself experiencing a lot of frustration trying to navigate the roads yourself. We can provide a guide to accompany you as you drive, or to drive you and your group in our vehicles or even on foot.

Boston was settled by William Blackstone in 1727, and was referred to as “The City Upon a Hill” back in 1630. The Freedom Trail includes Beacon Hill, Copps Hill, and the highest hill in Greater Boston – Bunker Hill. The Freedom Trail is nearly 6 miles round-trip, and bus and trolley tours are strictly prohibited from entering many of these areas, including Bunker Hill, Paul Revere’s House, the North End, Beacon Hill interior, and more.

Most Bus and Trolley tours will drop you off with a map to find your way, and when you are finished, you must navigate back to the commercial roads to wait at their stops for the next trolley or bus to pick you up. Because of these limitations, you may want to consider taking one of our driving tours if you have very young children or if you aren’t up to a long day of walking and/or hiking. However, if walking is right up your alley, our guides can accommodate you for part or all of the Freedom Trail, as well as for photo tours of all the sections of the photogenic city.

All our tours are personalized with your wishes and needs in mind – some sites may be worth more of what time you have here than others.