Best Boston History Tours

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If you are planning a trip to historic Boston you may be interested in taking one of the many Boston history tours available there. There are many tours to choose from but you only have so much time and money to spend.

Boston is a historic city with nearly four centuries of history to explore. With so many Boston historic sites to see, it’s hard to know where to start, what to see or even how to get there.

Fortunately, taking a history tour solves this problem for you because the tours takes you directly to all the important must-see sites.

The tour guides can also answer any questions you may have and give you more detailed, insider information that the travel books don’t have. The tours are affordable and fun and are one of the best ways to explore Boston.

To help you decide which tour is best for you. I’ve compiled a list of what are considered the best Boston history tours. These tours get great reviews from tourists on sites like Tripadvisor and Yelp and are the best-selling tours available.

The following is a list of the best Boston history tours:

Freedom Trail Tour:

The Freedom Trail Foundation offers many historical tours, including the Walk Into History Tour, the Reverse Walk Into History Tour and the North End Tour, and are led by tour guides dressed in 18th century clothing.

The Walk Into History tour is a 90 minute tour that stops at 11 of the 16 Freedom Trail sites:

Boston Common
Massachusetts State House
Park Street Church
Granary Burying Ground
King’s Chapel
Site of the First Public School
Old Corner Bookstore
Old South Meeting House
Old State House
site of the Boston Massacre
Faneuil Hall

The tour starts at Boston Common and ends at Faneuil Hall.

The Reverse Walk Into History tour is the same time except that it begins and ends in reverse locations, starting at Faneuil Hall and ending at Boston Common.

The North End Tour is a 90 minute tour that stops at three of the 16 Freedom Trail sites and various spots in the North End neighborhood, which includes the Paul Revere House, Old North Church, and Copp’s Hill Burying Ground. The tour starts at Faneuil Hall and ends at the North End along the waterfront.

Both public tours and private tours are available. Extended tours are also available. Public tours are available daily throughout the year. Tickets may be purchased online or at the departure location.

Private, group, and school tours are available at a preferred date, time, and departure location. Reservations are required. Contact the Freedom Trail Foundation to book a school, private, corporate, or group tour by calling 617.357.8300

Boston Duck Tours:

Boston Duck Tours offers a guided 80-minute tour aboard a WWII-style amphibious landing vehicle. The tour includes historic sites but isn’t solely a history tour and focuses on sites that made Boston famous. The company offers two tours, one which departs from the Prudential Center and one that departs from the New England Aquarium.

The tour that departs from the Prudential Center includes 36 notable Boston sites:

Prudential Tower
Christian Science Church
Copley Place/ Arts Square
New Old South Church
Arlington Street Church
Boston Common/ Public Gardens
Swan Boats
Beacon Hill
State House
Robert Gould Shaw Memorial
Mary Dyer
Old Scollay Square/ Government Center
Old West Church
West End
TD Garden
Zakim Bunker Hill Bridge
Museum of Science
Charles River
Esplanade
Longfellow Bridge
Hatch Shell
Bunker Hill
Main Street, Charlestown
Old North Church/North End
Rose Kennedy Greenway/North End Parks
Holocaust Memorial
Faneuil Hall/ Quincy Market
Old State House
King’s Chapel
Granary Burying Ground
Make Way for Ducklings
Cheers
Newbury Street
Trinity Church
Hancock Tower
Boston Public Library

The tour that departs from the New England Aquarium includes 32 notable sites:

New England Aquarium
Long Wharf
Rose Kennedy Greenway/Wharf District Parks
Custom House
Old State House
King’s Chapel
Granary Burying Ground
Arlington Street Church
Boston Common/ Public Gardens
Make Way for Ducklings
Cheers
Swan Boats
Beacon Hill
State House
Robert Gould Shaw Memorial
Mary Dyer
Old Scollay Square/ Government Center
Old West Church
West End
TD Garden
Zakim Bunker Hill Bridge
Museum of Science
Charles River
Esplanade
Longfellow Bridge
Hatch Shell
Bunker Hill
Main Street, Charlestown
Old North Church/North End
Holocaust Memorial
Faneuil Hall/ Quincy Market
Christopher Columbus Park

At the end of the tour, the duck boat launches into the Charles River for a view of the Boston and Cambridge skylines. Tours are seasonal. Tickets may be purchased online or in person. Telephone reservations are available for groups of 20 or more.

You can save money on this tour with Boston Duck Tours Coupons & Discount Tickets.

Free Tours By Foot:

Free Tours By Foot offers many different types of guided walking tours which includes the Freedom Trail Tour, North End and Little Italy Tour, Cambridge and Harvard Tour, Kennedy and Irish History of Boston, Beacon Hill Crime Tour, and the Boston Strong Tour: Fire, Flood and Famine.

The tours are a name-your-own-price model which means the company doesn’t charge for its tours and instead asks that you pay what you think the tour was worth. This is to ensure that the tour guide gives you the best tour possible.

The Freedom Trail Tour is a two-hour, one mile-long tour that explores various sites along the Freedom Trail including:

Boston Common
Massachusetts State House
Park Street Church
Granary Burying Ground
King’s Chapel
Old South Meeting House
Old Corner Bookstore
Old State House
Boston Massacre Site
Faneuil Hall and more

The tour starts at the Boston Common and ends at Faneuil Hall. Reservations are required and can be booked online.

The North End Little Italy Tour is a two-hour, one-mile long tour that explores the diverse history of Boston’s North End. The tour includes stops at some of the North End’s most famous and historic landmarks including:

Faneuil Hall
Quincy Market
Paul Revere House
Rose Kennedy’s Birthplace
Paul Revere Statue
Old North Church
St. Stephen Church
Copp’s Hill Burial Ground
Battle of Bunker Hill
Crime of the Century
The Skinny House
1919 Flood
Black Mass location and more

The tour starts at Faneuil Hall. Reservations are required and can be booked online.

The Cambridge and Harvard Tour is a two-hour, one-mile long tour that explores the history of Cambridge, Massachusetts that spans nearly four centuries. Sites included in the tour are:

Harvard Square
Harvard University
Cambridge Common
Washington Elm
Christ Church
Harvard Yard
Henry Wadsworth Longfellow House and more

Reservations are required and can be booked online.

The Kennedy and Boston Irish Tour is a two-hour, one-mile long tour that explores the history of Irish immigrants in Boston from the time of their arrival in Boston in the 19th century to the rise of Irish-American politicians, such as the Kennedy family, in the 20th century.

The tour includes stops at historical sites that are significant to Boston’s Irish history including:

John F. Kennedy Statue
The Old City Hall
The State House on Beacon Hill
James Michael Curley Statue
America’s First Subway
Rose Fitzgerald Kennedy Birthplace
St. Stephen’s Church
Mayor Kevin White Statue
The Union Oyster House
City Hall Plaza
Irish Famine Memorial
Omni Parker Hotel
The North End
The Old State House

The Beacon Hill Crime Tour explores the dark and violent history of the Beacon Hill neighborhood which was the location of various murders committed by the notorious serial killer, the Boston Strangler and a famous murder committed by Professor John Webster.

The tour includes stops at notable sites including:

home of Strangler victim Mary Sullivan
home of Strangler victim Ida Irga
house of Dr. Charles Parkman
house of murder victim Dr. George Parkman
site of Harvard Medical College
site of Charles Street Jail and more

The Boston Strong: Fire, Flood and Famine tour is a two-hour, one-mile long tour about the various tragedies and disasters that have occurred in Boston over the centuries and the cause, effects and aftermath of these events.

The tour includes stops at various sites where these events occurred, including:

Marathon Bombing Site
Hotel Vendome Memorial
The “Plywood Palace”
Site of the Coconut Grove Night Club Fire
A Strange Entombment
The Scourge of Boston 1721
“Combat Zone”
Great Fire of 1872
Boston Irish Famine Statue

The tour starts in front of the Boston Public Library and ends at the Boston Irish Famine Statue.

Boston By Foot:

Boston By Foot offers numerous standard history tours as well as a number of specialty topic tours that discuss more niche history topics.

The standard history tours include the Back Bay tour, the Beacon Hill tour, Boston by Little Feet tour, Heart of the Freedom Trail tour, Reinventing Boston: A City Engineered tour, Road to Revolution tour, the Dark Side of Boston, the Hub of Literary America, the North End: Gateway to Boston.

The Back Bay tour is a 90-minute tour that discusses how the area was once an actual bay that was later filled in and explains how the neighborhood developed in the 19th century to become the center of art and architecture in Boston. The tour stops at locations such as Trinity Church, the Boston Public Library, Old South Church, and various Back Bay townhouses.

The Beacon Hill tour is a 90-minute tour that discusses the history and development of the area from its beginnings as a rural hill to its development as one of the most wealthy neighborhoods that became home to some of Boston’s most prominent citizens.

The Boston By Little Feet tour is a 30 minute walking tour specifically for children between six and 12 years of age. The tour explores sites that played a key role in Boston’s history and also visits some of the oldest landmarks in the city. The tour includes ten sites in downtown Boston.

The Heart of the Freedom Trail Tour is a 90-minute walking tour of the Freedom Trail in downtown Boston. The tour explores the history of Boston from the early days of the Puritan settlement to the American Revolution to its more modern development.

The tour includes stops along 10 historic sites on the Freedom Trail such as the Old State House, Faneuil Hall, King’s Chapel, Old South Meetinghouse, and the site of the first public school in America.

Reinventing Boston: A City Engineered

The Reinventing Boston tour is a 90-minute tour that explores that various public works projects that have transformed Boston over the centuries. The tour discusses topics such as Boston’s maritime wharves, the history of the Boston subway and the Big Dig.

Road to Revolution

The Road to Revolution is a two-hour tour and is the company’s most comprehensive Freedom Trail tour. The tour explores famous landmarks such as King’s Chapel, the Old South Meetinghouse, the Old State House, the site of the Boston Massacre, the Paul Revere House and etc.

The Dark Side of Boston

The Dark Side of Boston tour is a 90-minute tour that explores the city’s more notorious history such as murders, disease epidemics, riots, robberies, disasters and etc. The tour takes place in the North End neighborhood.

The Hub of Literary America

The Hub of Literary America is a 90-minute tour that explores the history of Boston’s literary scene. The tour highlights the homes and hangouts of many prominent 19th century writers such as Ralph Waldo Emerson, Nathaniel Hawthorne, Henry David Thoreau, Louisa May Alcott, Henry James, Charles Dickens and Henry Wadsworth Longfellow.

The North End: Gateway to Boston

The North End tour is a 90-minute tour that explores the history behind one of Boston’s oldest neighborhoods. The tour discusses the many phases of the North End’s history such as its early Colonial days, the American Revolution, 19th century wave of immigrants to its modern day appearance.

In addition to these standard tours, the company also offers special topic tours such as:

Adams Family in Boston
Bay Village
Beacon Hill with a Boo!
Ben Franklin: Son of Boston
Boston by Bullfinch
Boston’s LGBT Past
Boston’s Opera House
Dams, Bridges & Locks
East Boston: Maverick Square and Beyond
Educating Boston
Fierce and Feminine: Great Women of Boston
Finding Aesop’s Fables in Copley Square
Footloose on the Freedom Trail
Fort Point Channel
Grave Undertakings: Boston’s Burying Grounds
Historic Waterfront
Johnny Termain’s Boston
Kendall Square
Longwood & Cottage Farm
Murder, Martyrs and Mysticism
SoWa: South of Washington Street
The Flat of Beacon Hill
The Making of MIT: From Back Bay to Cambridge
The Tipsy Tour: Dram Shops and Drunken Sailors
True Lies and False Facts: A Questionable Tour of Boston

Boston Segway Tours:

Boston Segway Tours offers two different tours, a one-hour tour and a two-hour tour, which are conducted on segways.

The one-hour tour starts at State Street and then makes its way to the center of the city, passing through the financial district, then continues on to the harbor before returning to State Street.

The two-hour tour starts at State Street, stopping at the Freedom Trail sites along the way including Faneuil Hall, the Old State House, Boston Common, the Public Garden, Granary Burying Ground, the New State House, King’s Chapel and Park Street Church, before continuing on to the financial district and then to the harbor.

The tour then continues on to Cambridge, exploring the neighborhoods of Beacon Hill, Bay Bay, Chinatown before returning back to State Street via the Rose F. Kennedy Greenway.

Since the segways can’t be operated on sidewalks or through places like Faneuil Hall, the tour company doesn’t offer a full Freedom Trail tour but both of the available tours do stop at various locations along the Freedom Trail that are accessible to segways.

Riders must be at least 14 years old to ride a segway and must weigh between 99 and 300 pounds. Electronic devices are not allowed during the tour for safety reasons so the tour company offers complimentary photos of you and your group on the tour.

Old Town Trolley Tours:

Old Town Trolley Tours offers a hop on and hop off tour where riders can leave the trolley and explore the sites at any time. The tour is a narrated, 1 hour and 50 minute tour that stops at 19 locations:

Faneuil Hall
Historic North End
USS Constitution and Museum
North Station/ TD Garden
Downtown Crossing / Historic District
Trolley Stop Store / Theater District
Cheers Bar
Copley Square / Back Bay
Christian Science Plaza / Symphony Hall
Copley Plaza Mall
Prudential Center
Fenway
Cambridge / Harvard / MIT
Beacon Hill / Antique Row
State House / Boston Common
Boston Tea Party Ships & Museum
South Station
Boston Convention Center
Massport/Black Falcon Cruise Ship Terminal
Boston Fishing Pier

You can save money on this tour with Boston Old Town Trolley Coupons & Discount Tickets.

CityView Trolley Tours:

CityView Trolley Tours offers a hop on and hop off tour where riders can leave the trolley and explore the sites at any time. The tour is 45 minutes long and stops at nine locations:

New England Aquarium
Paul Revere House / Little Italy
North End / Old North Church
USS Constitution
North Station
Old State House / Faneuil Hall
Boston Common
State House / Beacon Hill
South Station / Boston Tea Party Ship Museum

City View Trolley Tours offers tours year round, but hours of operation are limited during the winter. Tickets can be purchased online or over the phone.

You can save money on this tour with Cityview Trolley Coupons & Discount tickets.

Walking Boston:

Walking Boston is a private walking tour of historic Boston by tour guide Ben Edwards. Edwards is a Boston historian with a family history that reaches back to 17th century Boston.

In fact, Edwards is related to Paul Revere through the marriage of his ancestor, Sally Edwards, to Revere’s eldest son, Paul Revere, Jr, and his tour even has a letter of recommendation from the Paul Revere House.

Walking Boston tours cover all of the Freedom Trail sites, several secret spots and goes inside King’s Chapel, Faneuil Hall and all three burying grounds. Walking Boston offers two types of tours: a 4.5 hour tour and a 5.5 hour tour. The 4.5 hour tour includes stops at 15 locations:

Massachusetts State House
Boston Common
Park Street Church
Granary Burying Ground
King’s Chapel
King’s Chapel Burying Ground
Old Corner Bookstore Building
Old South Meeting House
Old State House
Boston Massacre Site
Faneuil Hall
Paul Revere House (exterior only)
Old North Church
Copp’s Hill Burying Ground
Secret / Hidden Spots

The 5.5 hour tour includes all of the above but also includes a tour of the Paul Revere house and a lunch break at the historic Union Oyster House.

Boston Walking Tours are a more in-depth type of tour for people who are interested in learning more and spending more time exploring the history of Boston.

Due to the length of the tours and the amount of information each tour provides, the tours are a little pricier than the average history tour but is well worth it if you are looking for something better than a simple hour-long tour.

Tours run from March until December. Reservations are required and can be made online or over the phone at 617-670-1888.

Lessons on Liberty Walking Tour:

Lessons on Liberty Walking Tour offers a 90-minute walking tour of Boston’ Freedom Trail. The tours are led by historians and teachers, not actors, dressed in 18th century clothing.

The tours discuss not only the events of the American Revolution but the events that led to the revolution as well. The tours include stops at number of historic sites including:

Boston Common
Granary Burying Ground
King’s Chapel Burying Ground
Boston Latin School
Old South Meeting House
Old State House
Boston Massacre Site
Faneuil Hall and more

Tours run from April to October and tours can be booked online.

Sources:
Boston By Foot: Frequently Asked Questions: www.bostonbyfoot.org/faq#overlay-context=
Walking Boston: Letter of Recommendation from the Paul Revere House: walkingboston.com/revere-house-letter/
TripAdvisor: The Top 10 Best Boston Tours: www.tripadvisor.com/Attractions-g60745-Activities-c42-Boston_Massachusetts.html
CBS Boston: Boston’s Best Historical Tours: boston.cbslocal.com/top-lists/bostons-best-historical-tours/
Boston Discovery Guide: Boston Sightseeing Tours: www.boston-discovery-guide.com/boston-sightseeing-tours.html
Walking Boston: The Edwards Family in Boston: walkingboston.com/wp-content/uploads/2016/02/Edwards-Family-in-Boston-2.1.2016.pdf

About Rebecca Beatrice Brooks

Rebecca Beatrice Brooks is the owner and operator of this website and all the articles are written and researched by her. Rebecca is a freelance writer and history lover who got her start in journalism working for small-town newspapers in Massachusetts and New Hampshire after she graduated from the University of New Hampshire with a B.A. in journalism. Visit this site's About page to find out more about Rebecca.

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