Dan Mattingly - Guide


Dan is an urban investigator, who is eager to share his curiosity of Boston with all those who are willing. Ten years in the tourism business gives him a great footing in helping you explore the side of Boston you want to see. A believer in "To ask is to know" all questions are Dan's catnip. His strong preference for travel by foot and the "T" allows you to experience the city authentically.


Our Ride...


For the riding portion of select tours, you will ride in a comfortable, spacious mini-van with all leather seats, large windows and a front to back sunroof!

Seating for 6 guests (without luggage) or 4-5 guests with some luggage. Child car-seat available upon request.


The most knowledgeable guides with years of experience

Our guides are the best of the best with many years of experience. You will enjoy your time with our knowledgeable and friendly guides as they show off the city they love.

Trip Advisor

Our Guides


Neal Roberts, Manager/Guide


A Boston native, Neal has been a licensed guide for 32 years. As a father of three, as well as a middle school teacher he welcomes families on all of his tours which are fun, educational, informational, and entertaining. Neal knows all the "ins and outs" of Boston and the surrounding areas and was also a concierge for a large Boston hotel so he is glad to help you with restaurants, shopping and other excursions as well.


Neal holds two masters degrees in education plus has an extensive art, design and photography background which comes in handy on his tours.  You will learn a lot on your tour, but more importantly, you will have fun. He is a firm believer in a balanced tour without an "overload" of facts and figures that most people won't remember anyway. You will leave knowing a great deal about his home town but will also go home with a smile on your face. Sightseeing should always be fun, never boring. Neal is also a huge Boston sports fan and will happily show you where our teams win championships!


Since Neal is also a school teacher, his tours run weekend days in the winter, spring and fall as well as many weekdays during the summer. (Weekday tours during the school year after 2:30PM) You will always find him at the Boston Marathon finish line each year on Patriots Day in April as an official BAA finish-line volunteer. Now and always...Boston Strong!


B O S T O N   S I G H T S E E I N G   T O U R S,  LLC

Richard T. Holland, Sr.   AKA  John Larkin  - Guide

Richard been conducting tours of Boston, Concord, Lexington, and Salem for the past 30 years. Richard T. Holland, Sr. is the real deal. He is, quite literally, a walking encyclopedia. Born and raised in Boston, he conducted historical tours both locally and abroad for over 30 years. He earned a Masters degree in Education from Gordon College.

Richie's motto is “Give the best tour possible, so the tourist, hopefully, will tell 5 other people to take my tour, so that should mean I have a job next year."