Experience Charlestown like a local — historic, scenic, and unforgettable. Book a tour with Boston To Salem Tours and step into one of Boston’s most charming neighborhoods with guided experiences that bring history to life and deliver picture-perfect views.
Why choose a Charlestown tour?
Rich history: Walk the cobblestone streets and learn stories of the Revolutionary War, shipbuilders, and famous residents. See the USS Constitution (“Old Ironsides”) and hear the tales that shaped the nation.
Breathtaking vistas: Stand atop the Bunker Hill Monument and enjoy sweeping views of the Boston skyline and harbor — ideal for photos and lasting memories.
Expert guides: Knowledgeable, engaging local guides provide accurate history, compelling anecdotes, and a friendly, professional experience from start to finish.
Small-group comfort: Our tours are intimate by design, allowing for personal attention, easy Q&A, and a relaxed pace that suits all ages.
Convenient logistics: Centrally located meeting points, clear directions, and punctual departures make your day effortless. We handle the planning so you can focus on enjoying the moment.
Perfect for:
First-time visitors who want an efficient, in-depth introduction to Boston’s Revolutionary past.
History buffs seeking primary sites and expert commentary.
Families and groups looking for an educational, fun outing.
Photographers and sightseers wanting iconic Boston views.
Book now and get:
A guided walking tour that covers Charlestown’s top landmarks and hidden gems.
Insider stories and local tips you won’t find in guidebooks.
Flexible scheduling and friendly customer service to tailor the experience to your needs.
Step inside the scenes of Hollywood’s favorite Boston backdrop.
Ever wondered if the "bank robbery capital" reputation is real? From the intense chases of Ben Affleck’s The Town to the heartfelt steps of Good Will Hunting, Charlestown has played a starring role in cinema for decades. On this 90-minute walking tour, we move past the history books and into the scripts.
Tour Highlights:.
What’s Included:
Expert Storytelling: Local insights into the story behind the FiLM! Secrets only residents know and how the neighborhood really felt about the film.
Photo Ops: Exact Locations - access to private property
Small Group Size: An intimate experience—no megaphones or crowded buses.
Contact us for special group rates of 6 or more
This historical parade brings families back to the town year after year.
Train Stop: Community College
Parking: Cambridge Street/Spice Street Parking Lot: $6.00 day
The 2026 Charlestown Bunker Hill Day Parade is scheduled for Sunday, June 14, 2026. This year is particularly significant as it marks the 250th Anniversary of the Battle of Bunker Hill, so the festivities are expected to be even larger than usual.
The Bunker Hill Parade commemorates the Battle of Bunker Hill, the armed services, and the essence of American heritage while celebrating the historic neighborhood of Charlestown.
One of the longest-standing parades in the United States, this event serves as a bridge between commemoration and celebration, dating back to 1786.
Beyond the Monument lie the stories of the people who built Boston. This tour takes you into the heart of Charlestown to uncover the narratives that history books often skip.
Bunkerhill Monument, The Constitution, The Warren Tavern, Phipps Burying Ground, Sites- from The Movies “ The Town” “ Goodwill Hunting”
The Irish Legacy: Trace the footsteps of the immigrants who transformed this neighborhood into a vibrant cultural hub.
The Warren Tavern- The oldest tavern in Massachusetts, once a favorite haunt of Paul Revere and George Washington.
Join Boston To Salem Tours for an intimate look at the legends, scandals, and survival of Boston's oldest neighborhood.
2.5 hr Tour - sneakers recommended
TRAIN Stop: Orange Line Bunkerhill Community College
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