A born-and-raised Bostonian with decades of guiding experience, Neal genuinely enjoys showing off his hometown. Whether it’s a first visit or a return trip, he helps guests explore Boston in a way that’s fun, informative, and tailored to their interests.

Before guiding full-time, Neal spent many years as a middle school teacher while leading tours on weekends and during the summer. That background shaped his ability to keep tours engaging for all ages. His approach blends history, storytelling, architecture, and hidden gems with just the right amount of trivia. Guests leave not only knowing more about Boston, but also having laughed, taken great photos, and truly enjoyed the experience. His philosophy is simple: tours should always be fun, never boring.

He has worked as an operations manager for a major sightseeing company and as a hotel concierge, giving him a well-rounded perspective on both the city and the visitor experience. He currently serves on the Board of Directors of the Greater Boston Tour Guide Association and holds two master’s degrees in education.

Whether you have a few hours or a full day, Neal will make your time in Boston memorable for all the right reasons.

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.

Tracy grew up in the Boston area and brings both warmth and energy to every tour she leads. A natural communicator and gifted storyteller, she studied education before building a career in customer service and later becoming a professional guide.

With well over a decade of guiding experience in both Boston and Hawaii, Tracy has a deep appreciation for what makes each place unique. Boston, however, is where her heart is. She loves sharing the city’s rich history and folklore, and takes pride in creating tours that are engaging, approachable, and memorable.

She brings a relaxed, conversational style to her tours, making each experience feel personal rather than scripted.

Tracy enjoys meeting people from around the world and traveling whenever she can. When she’s not guiding, she can often be found walking or training her deaf dog, Bohdi

Seán is a Bostonian through and through. Raised in nearby Cambridge, he spent years exploring every corner of the city and developing a deep connection to the region.

An adventurous traveler at heart, Seán has logged thousands of miles throughout New England by canoe, car, and motorcycle, along with international journeys that broadened his perspective along the way. After years of traveling, he returned to Boston, drawn back by its rich history, vibrant culture, and unmistakable character.

With a passion for storytelling and a deep knowledge of the city, Seán brings Boston to life in a way that is engaging, approachable, and memorable. He is known for his attention to detail and takes pride in making sure every part of the experience is thoughtful, well-paced, and easy to follow.

Friendly and welcoming, Seán creates a relaxed, conversational atmosphere where guests feel comfortable, involved, and never rushed. His tours feel personal rather than scripted, giving visitors a genuine connection to the city.

PJ brings a strong background in marketing, event planning, and trade show management to his role as a Boston guide. With a passion for both history and hospitality, he approaches each tour as both a host and an educator, focused on creating a smooth, memorable experience for every guest.

Rather than simply reciting facts, PJ brings history to life by connecting the past to the present through engaging storytelling and clear, thoughtful explanations. His tours are informative, approachable, and easy to follow, keeping guests interested from start to finish.

With experience guiding throughout Boston and the surrounding region, including Cambridge, Lexington and Concord, Plymouth, Salem, and Cape Ann, PJ is comfortable working with groups of all sizes. Whether leading a small private tour or a larger group, he delivers a well-organized, engaging experience with strong attention to detail.

Naomi, a Cambridge resident for over 40 years, has been guiding tours throughout Boston and the surrounding region for decades. Her experience spans Boston, Cambridge, Lexington and Concord, Salem, Plymouth, and the North Shore.

With a background in education, Naomi brings a thoughtful and engaging approach to her tours. She enjoys presenting both history and current-day insights in a way that is clear, entertaining, and accessible to a wide range of audiences.

Naomi has extensive experience working with students, senior groups, and international visitors, and is especially skilled at adapting her tours to meet different interests and needs. She has also developed specialized tours tailored to a variety of groups.

A fan of history, architecture, and the diverse landscapes of the Boston area, Naomi brings a calm, attentive presence and a gentle sense of humor to every tour. Her approach is relaxed, scenic, and engaging, leaving guests both informed and smiling.

Shannon has been a Boston tour guide and tour director since 2017 and lives in the Roslindale neighborhood of the city. After completing her training at the International Tour Management Institute, she began guiding shortly after and has been sharing Boston’s history and character with visitors ever since.

With experience as both a guide and a tour director, Shannon brings a well-rounded perspective to her work. She understands not only how to deliver an engaging tour, but also how to create a smooth, well-organized experience from start to finish.

Her background in leadership and organizing dates back to 2004 and includes running Alternative Spring Break programs, teaching college courses on organizing, and leading multi-day retreats. She has also worked in Antarctica, serving on the Leadership Board with the National Science Foundation.

Shannon combines her love of storytelling with a natural ability to bring people together. Her tours are engaging, well-paced, and thoughtfully organized, creating experiences that are both meaningful and memorable.

Ellie was born in Scotland and grew up just outside of Boston, a city she believes is one of the most beautiful in America. She loves sharing Boston’s history and charm with her guests and especially enjoys seeing their reactions as they discover something new and fall in love with the city themselves.

Ellie believes that people may arrive as strangers, but often leave her tours as friends. Her warm, welcoming approach creates a relaxed and enjoyable experience for guests of all backgrounds.

Before becoming a guide, Ellie spent over 40 years working for the State of Massachusetts, overseeing Unemployment offices and Career Centers. She often encouraged others to follow their passion when facing a change in direction, and after retiring, she chose to do just that by becoming a tour guide.

For Ellie, guiding is about creating exciting discoveries, new experiences, and shared memories. She looks forward to meeting each guest and making their time in Boston truly special.

Michael is a lifelong Boston resident and a retired Boston Public Schools educator who brings a deep knowledge of the city and a passion for storytelling to every tour he leads.

With years of experience exploring Boston’s history, Michael focuses on uncovering the stories that are often overlooked. He has a particular interest in the Underground Railroad and the individuals who played a role in helping others find freedom, adding depth and meaning to the places visitors see along the way.

Whether guiding along the Freedom Trail or exploring Boston’s Black history, Michael goes beyond the standard landmarks to provide a richer, more thoughtful perspective. His tours are engaging, informative, and designed to leave guests with a deeper understanding of the city and its past.

Francine is an educator, lifelong learner, and natural leader with a deep passion for travel and history. While her travels have taken her across the globe, her true love remains her hometown of Boston.

A graduate of the University of Massachusetts, Francine has been guiding tours throughout Massachusetts for many years. She is known for her welcoming spirit and the genuine enthusiasm she brings to every experience.

With a strong interest in Boston’s history and traditions, Francine creates tours that are engaging, informative, and easy to connect with. Her energy is contagious, and she takes great joy in helping guests better understand and appreciate the city.

Ernie is a Boston-area native, something you’ll likely pick up on right away from his unmistakable accent. With many years of guiding experience, he brings energy, humor, and a love of storytelling to every tour.

For Ernie, guiding is a chance to teach, entertain, and connect with people. He enjoys bringing history to life in a way that is engaging and easy to follow, creating an experience that is both fun and memorable.

A natural storyteller, Ernie especially enjoys leading guests along the Freedom Trail, where he shares the people, events, and moments that shaped Boston and the nation.

Ruth has had a lifelong passion for Boston history and a deep appreciation for the stories that have shaped the city. She finds great joy in sharing that passion with others, helping visitors connect with Boston in a meaningful and memorable way.

A professional singer, voice teacher, and performer, Ruth brings a unique presence to her tours. With training from the New England Conservatory and graduate studies at the Vienna Academy of Music, she has spent years performing on stage and working with audiences of all kinds.

That background carries directly into her guiding style. Ruth has a natural ability to project, engage, and connect, making her tours easy to follow, expressive, and enjoyable. Her sense of timing, delivery, and storytelling helps bring Boston’s history to life in a way that feels both polished and personal.

Warm, engaging, and thoughtful, Ruth creates a relaxed atmosphere where guests feel comfortable, involved, and inspired by the stories she shares.

After graduating from college nearly thirty years ago, Bill came across a job posting for tour guides and decided to give it a try. The rest is history. Since then, he has built a deep knowledge of Boston and the surrounding area through years of reading, research, and hands-on experience.

Known to many as “Coach,” Bill brings the same energy and enthusiasm to his tours that he has shown over the years coaching his three children. His passion for sports and love of working with people come through in every experience he leads.

Guests consistently remark on Bill’s ability to present history in a way that is both fun and informative. His tours are engaging, easy to follow, and filled with the kind of insight that makes Boston’s story come alive.

Richard has been leading tours throughout Boston, Concord, Lexington, and Salem for over 40 years. Born and raised in Boston, he brings a deep, firsthand connection to the city along with decades of experience guiding both locally and abroad.

Often described as a “walking encyclopedia,” Richard has built an extensive knowledge of Boston’s history through years of study and hands-on experience. He holds a master’s degree in education from Gordon College and has a natural ability to share information in a way that is clear, engaging, and easy to understand.

Richard approaches every tour with a simple philosophy: “Give the best tour possible, so the guest will tell five other people to take my tour.” That mindset shows in his dedication, depth of knowledge, and commitment to making each experience worthwhile.

For over 15 years, Mary Margaret has enjoyed sharing Boston with visitors from around the world. Whether exploring the city’s historic neighborhoods and rich past or its vibrant, ever-evolving areas, she creates experiences that leave guests excited to return and discover even more.

A graduate of Regis College and the Harvard Graduate School of Education, Mary Margaret brings a thoughtful and engaging approach to her tours. She combines her knowledge of the city with a warm, welcoming style that makes guests feel comfortable and involved throughout the experience.

Mary Margaret lives in Boston with her husband and is an active 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.

Amber, as she likes to say, “like waves of grain,” is a true Bostonian, born and raised in the heart of the city. With a natural flair for entertaining, she brings energy, personality, and a love of storytelling to every tour she leads.

With a professional background in both guiding and entertainment, Amber creates experiences that blend education with fun. She has led countless guests through Boston’s streets, weaving together stories of the city’s history and culture along with lighter topics like ghost stories, film locations, and local lore.

Amber’s tours are lively, engaging, and full of personality, offering a fresh and memorable way to experience Boston beyond the typical approach.

A native of France and a kindergarten teacher, Virginie has been giving bilingual tours of Boston and the surrounding region since 1998 alongside her teaching career.

With her background in education, she presents Boston’s history in a clear, engaging, and interactive way that works well for audiences of all ages. Fluent in both French and English, she is especially skilled at making tours accessible, informative, and enjoyable for international visitors.

Virginie’s approach is thoughtful and structured, combining strong storytelling with a warm, approachable style that keeps guests involved from start to finish.

Josh grew up in the Boston area and loves introducing visitors to the incredible range of experiences the region has to offer. With a background as an educator, facilitator, and designer of learning experiences, he brings creativity and intention to every tour he leads.

In addition to guiding, Josh works as a writer, actor, and theatre director, and has led international trips with students and adults. He holds a master’s degree in theatre education from Emerson College and is a graduate of Vassar College. A Fulbright Fellow in Colombia and a fluent Spanish speaker, he enjoys connecting with people from all over the world.

Josh’s tours are interactive, flexible, and highly personalized. With a strong storytelling background and an improvisational style, he brings Boston’s history and culture to life in a way that feels engaging, thoughtful, and fun.

After a legal career spanning more than 40 years, Dick has spent the past eleven years sharing Boston’s rich history with visitors from across the country and around the world as a tour guide.

His background in law brings a thoughtful and analytical perspective to his tours, along with a strong ability to communicate complex ideas in a clear and engaging way. He enjoys presenting Boston’s history with context and insight, helping guests better understand not just what happened, but why it matters.

Dick finds interacting with guests to be one of the most rewarding parts of guiding. He takes pride in creating an experience that is both informative and enjoyable, making sure that each guest feels their time on tour is time well spent.

Pat has been guiding tours and training new guides for over 30 years, bringing a deep knowledge of Boston’s history and a wealth of experience to every tour he leads.

He combines a strong understanding of the colonial era and 19th-century Boston with stories and anecdotes that highlight everyday life in the city. His expertise in the events leading to Lexington and Concord, as well as the causes of the American Revolution and Boston’s role in it, adds depth and context that guests find both informative and engaging.

In addition to Boston, Pat has a strong knowledge of Cambridge, including Harvard University, as well as Beacon Hill and Back Bay. His tours are educational, well-paced, and designed to give guests a clear and enjoyable understanding of the city and its history.

Ellen is a New England native and a graduate of Boston University who has been guiding tours in Boston since 2015.

What started as a monetized hobby quickly grew into something more, and she can now often be found leading historical walking tours throughout downtown Boston year-round. During the quieter winter months, Ellen takes the opportunity to dive deeper into research on the American Revolution and Boston’s history, continually expanding her knowledge.

Ellen’s tours reflect her curiosity and enthusiasm, combining solid historical insight with a relaxed, approachable style. She enjoys helping guests connect with the city in a way that feels both informative and enjoyable.

When she’s not guiding or reading, Ellen can often be found visiting museums and historic sites or working her way through a growing travel bucket list.

Brian has been guiding tours in Boston for over two decades, bringing a deep knowledge of the city and years of hands-on experience to every tour he leads.

He has worked with groups of all sizes, helping visitors explore Boston’s most iconic landmarks while also sharing the stories that give the city its character. His approach is engaging and easy to follow, making the experience enjoyable for both first-time visitors and returning guests.

Brian takes pride in showcasing his hometown to travelers from around the world. His steady, approachable style and genuine enthusiasm create tours that are both informative and memorable.

Robin has a strong interest in Boston’s lesser-known stories and specializes in creating tours that explore parts of the city often overlooked by traditional itineraries.

She conducts tours that focus on the people, neighborhoods, and industries that shaped Boston over time. Her approach connects past and present, giving guests a deeper understanding of how the city has evolved beyond the more familiar landmarks.

Robin also offers presentation-style programs that combine storytelling with images of the sites, making her work accessible and engaging for a wide range of groups.

Dagmar leads our German-language tours, offering a seamless and engaging experience for German-speaking visitors exploring Boston. As a native German speaker, she brings an added level of authenticity, making each tour feel natural, comfortable, and easy to follow.

Guiding in German isn’t just about translation. It’s about capturing the tone, humor, and meaning behind the stories. Dagmar does exactly that, ensuring her guests experience Boston the way it’s meant to be understood.

Whether she’s working with a small private group or a larger tour, her focus is always the same: make the experience smooth, informative, and genuinely memorable.

With over a decade of experience guiding in Boston, [Guide’s Name] has been sharing the city’s stories with visitors since 2010. He got his start on Boston’s busy hop-on, hop-off tours, where he learned how to keep things engaging, flexible, and fun for all kinds of groups.

A former Boston Public Schools teacher, he brings a natural ability to explain history in a way that’s clear, relatable, and never dry. He loves leading a step-on tour for a motorcoach group showing guests the city’s neighborhoods, while knowing how to read a crowd and make each tour feel personal.

His approach is simple: keep it interesting, keep it real, and make sure people walk away feeling like they actually experienced Boston, not just checked off a list of sites.

Henry is a retired school teacher and a longtime Boston tour guide whose experience and knowledge run deep. Over the years, he has guided countless visitors through the city, developing a thoughtful, easygoing style that reflects his background in education.

While he has stepped back from regular guiding, Henry remains part of our extended team. On the rare occasions he joins us, guests benefit from his steady presence, clear storytelling, and deep understanding of Boston’s history and character.

It’s not often you get the chance to tour with someone who has spent a lifetime both teaching and guiding. When you do, it shows.

Cloudy brings an international perspective and a love of storytelling to her tours. Having grown up between Hamburg, Germany and the New York area, she developed an early appreciation for different cultures and languages.

After raising three children, Cloudy followed her lifelong connection to the sea, working on tall ships in the Caribbean and now co-owning Liberty Fleet of Tall Ships based on Boston’s waterfront.

She quickly found a passion for sharing Boston’s history and architecture, especially with families. Cloudy has a natural ability to connect with both children and adults, making history feel fun, accessible, and engaging.

Her tours are warm, interactive, and full of discovery, helping guests see the city through fresh eyes and enjoy the experience together.

Christian is a highly regarded Boston guide known for his deep knowledge of the Revolutionary era, particularly the events surrounding Lexington and Concord.

With a passion for history and a talent for storytelling, Christian brings stories to life in a way that is detailed, engaging, and easy to follow. His tours go beyond the surface, helping guests understand not just what happened, but the people, decisions, and tensions that shaped those events.

Christian is always happy to share local recommendations for dining and exploring, helping guests make the most of their time in the Boston area.

Bill is a Salem resident and experienced guide with a strong background in both history and music. He has led tours in the region for many years and is known for bringing a thoughtful and engaging perspective to the stories he shares.

Before becoming a guide, Bill spent over three decades teaching music. His background as an educator is reflected in his clear, approachable style and his ability to connect with a wide range of audiences.

Bill has also been active in the local community, serving as chairman of the Historic Derby Street Neighborhood Association.

His tours combine local knowledge, historical insight, and a steady, engaging delivery that makes the experience both informative and enjoyable.

A seasoned raconteur, Salem historian, CPA, and former sports/news journalist. Giovanni has always had a love for history and antiquity so giving tours in a major historic city is a perfect fit. "Seeing the expression on guests' faces when I tell them our history provides the same joy for me as watching someone open a present I just gave them," he says.

He has been giving tours and has studied Salem's history for over 14 years. Giovanni has also performed standup, improv, and sketch comedy throughout New England and NYC and continues to do so. He is a SAG actor, having been in local and feature films, including Psychotica, Friction, Central Intelligence and Daddy’s Home 2.

Manny B. is a lifelong Cambridge resident with a deep knowledge of Boston and the surrounding area. With a background in political science from Boston College and decades of professional experience, he brings a thoughtful and well-rounded perspective to every tour.

Fluent in Portuguese, Manny connects easily with a wide range of guests and is especially well suited for international visitors. Since 2018, he has been guiding tours throughout Boston, including the Freedom Trail and citywide scenic tours, sharing both the city’s history and its present-day character.

Manny combines local knowledge, real-world experience, and a genuine appreciation for Boston’s history to deliver tours that are both informative and engaging.

Aline leads engaging walking and bus tours that explore the city’s history, architecture, and lesser-known stories. Her tours range from classic historical routes to themed experiences, all designed to be informative, accessible, and memorable.

With a background in communications, she brings a strong storytelling approach to her work, turning complex history into clear, engaging narratives that resonate with a wide range of audiences.

We remember Paul who was a legend in the Boston tour business where he gave me a job that ultimately would become a way of life for me. He began with a van in 1974 and built it into a company that would show thousands of visitors around Boston with his small fleet of buses. He was willing to show off a city that was old, dirty, and rough when others would not and saw the city he loved grow into a beautiful, vibrant tourist mecca.

Paul brought his knowledge, humor, and artistic talents to work every day where you would find his short pencil graveyard, eclectic office decor, and entertaining morning rituals. For 30 years I called him a colleague, boss, and friend and I truly thank him for the opportunities and the friendship.

Boston seems a little emptier today without Paul showing it off.

-Neal

All amazing guides who are camera shy apparently

Mike
Naim
Adri
Melanie
Steve
Dan
James #1
James #2