About

Lead Guide Neal has been a licensed guide for 35 years and is a member of the Greater Boston Tour Guide Association. As a father of three, as well as a newly retired 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 master's degrees plus he 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!

Naomi, a Cambridge resident for 40 years, has enjoyed guiding tours in Boston, Cambridge, Lexington, Concord, Salem, Marblehead, Gloucester, Plymouth, and the wider environs for decades. With a degree in education, she finds guiding an opportunity to present history and current information in a fun, entertaining way. She appreciates the interests of students and senior citizens alike and has developed tours for many specialized niches. Having worked with many international students and adults.

Naomi has left those groups with the cultural and historic aspects that make Boston shine. A fan of history and architecture, and urban, waterfront, and country landscapes, her gentle humor, and attentiveness will keep you smiling on her scenic, captivating tours.

Ellie was born in Scotland but grew up just outside of Boston which she believes is one of the most beautiful cities in America. She loves sharing the history and beauty of Boston with everyone on her tours and enjoys seeing the faces of her guests light up when they see and experience something new and exclaim how much they too love the city. Ellie feels that people on her tours start out as strangers but leave as friends.

Ellie worked for the State of Massachusetts for over 40 years overseeing Unemployment offices and Career Centers, she always told people that if they had a change in their employment status they should take that opportunity to follow their passion; this is just what Ellie has been doing since her retirement two years ago.

What matters to Ellie is providing exciting discoveries, new experiences, and shared memories. She can’t wait to meet you

For over three decades, Cindy has painted Boston's vibrant history onto the hearts of countless travelers. But her expertise extends far beyond guidebooks! By day, she weaves captivating narratives for visitors, and by night, her pen crafts whimsical children's stories. In fact, you might even say storytelling runs in her blood - she's a descendant of a Plymouth Elder, not to mention two signers of the Declaration of Independence (one of whom doubled down with a signature on the Constitution!).

Exploring Boston on foot is Cindy's passion. Imagine strolling cobbled streets, where each step whispers tales of revolutionaries, literary giants, and everyday heroes. With Cindy as your guide, history isn't a dusty textbook, it's a living, breathing adventure! Prepare to be charmed by her wit, captivated by her knowledge, and transported by the rich tapestry of Boston's past, present, and future.

Dan is an urban investigator, who is eager to share his curiosity of Boston with all those who are willing. Over 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.

Caitlin is a Texan transplanted for the love of Boston and an enduringly curious soul. She is a voracious reader and an ever-eager explorer of the wide and wonderful world.

She moved to Boston seven years ago after two brief visits because she felt a real connection to the city. There is so much history and culture here! While Caitlin has been giving tours for six years, she is still constantly learning new things and finding new hidden treasures, and it gives her great joy to be able to share this marvelous place!

Caitlin feels that by walking in the footsteps of the people who made history, seeing where they lived, and hearing their stories where they happened, history can truly come alive. From the Puritans to the American Revolution to the cultural and industrial revolutions of the 19th century and onward, Boston has it all. And it's all so close together, we can walk the same path five different times and uncover a new story each time!

An educator and lifelong learner, a traveler at heart, Francine is a gifted and talented natural leader. Her passion for travel has taken her all over the world, from Antarctica to Mt. Everest, but her true love is her hometown of Boston Massachusetts. Francine has worked as a Travel Guide in her native Massachusetts for many years and is fondly remembered by her guests for her welcoming spirit and the friendliness and enthusiasm that she unfailingly brings to her profession.

A graduate of the University of Massachusetts and an avid student of history, Francine brings the history and traditions of Boston to those fortunate enough to have her as a Guide. Her enthusiasm for touring is contagious! “I love sharing my beloved city of Boston with visitors, it’s such great fun to spend time helping my guests to understand and appreciate this beautiful part of our world.”

Manny has lived around the world, including Thailand, Taiwan, China, the Philippines, and Australia. During his time abroad, he found himself giving tours of these cities to friends and family. Now back in Boston, he is sharing his version of the city with our guests - showing you parts of the city that you may not ordinarily experience. This is especially important to Manny. "There's nothing more that I hate than experiencing a sanitized and dull version of a city. I want to know what really happened in a place and why and what sort of effect it had on the people."

He looks forward to exploring Boston with people who want a deeper, more nuanced understanding of what Boston has to offer - culturally, artistically, and societally.

Richard has 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 Master's 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."

For over 10 years, Mary Margaret has enjoyed showing off Boston to her visitors. Whether they are interested in Boston’s famous historic neighborhoods and its storied past or captivated by its vibrant new neighborhoods and bustling energy, everyone has a wonderful time. Mary Margaret’s favorite part of these tours is hearing how many people want to return to Boston and explore more of our fascinating city.

A graduate of Regis College and Harvard School of Ed, Mary Margaret and her husband live in Boston. She is a member of the Greater Boston Tour Guide Association, the Greater Boston Convention and Visitors Bureau, and the faculty of the Brookline Adult and Community Education program.

Brian has been a Boston guide for over two decades. From leading groups of all shapes and sizes to explore the city's most iconic landmarks, Brian is the ultimate guide for anyone looking to discover the heart and soul of Boston. With a passion for showcasing his hometown to travelers from all around the world, Brian's enthusiasm is sure to leave you spellbound.

His name is Seán

Seán isn't just a Boston tour guide, he's a Bostonian through and through. Growing up in Cambridge, he explored every corner of the city. His adventurous spirit took him beyond Boston, canoeing and hiking throughout New England. He's clocked thousands of miles exploring the region, by motorcycle, car, and even on international motorbike journeys. After years of traveling the world, Seán returned to Boston, captivated by its rich history, vibrant culture, and natural beauty. He's passionate about sharing his deep knowledge and love for this special place, where innovation, delicious food, and a significant role in American history come together.

Bill S, Cloudy, Manny B, Mike, Robin, Rob, Scott, James, Adri, Christian, Ernie, Naim, and Melanie.

Boston Sightseeing Tours is growing, and we are looking to add additional guides and tour options for our guests. We are looking for experienced guides to conduct walking and step-on tours of Boston, Cambridge, Lexington, Concord, Salem, and Plymouth as well other locations in the Boston area including specialty tours of individual neighborhoods and themes. Please call us at 617-285-6696 or email info@bostontours.com for more information.