Top Massachusetts Private Sightseeing Tours

Q: What are the best options for Massachusetts Private Sightseeing Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Massachusetts Private Sightseeing Tours are: App-Guided "Historic Boston Downtown Freedom Trail" Walking Tour Boston Harborwalk & Tea Party Self-Guided Walking Audio Tour Visit Historic Concord on a Private Day Trip from Boston Private North End Neighborhood Tour Lexington and Concord 3 hour private car tour from Boston

Q: What are the best kid-friendly options for Massachusetts Private Sightseeing Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Massachusetts Private Sightseeing Tours are: Boston Private Food Tour with 6+ Authentic Tastings Chatham Bites and Sights Walking Guided Food Tasting Tour Private North End Neighborhood Tour Boston and Cambridge City Tour Provincetown West End History Tour View all kid-friendly Tours →

Q: I need a ride! Which Massachusetts Private Sightseeing Tours have Hotel Pickup?

No problem. These Massachusetts Private Sightseeing Tours include Hotel Pickup: Boston Private 3-Hour Tour by Car Experience Martha's Vineyard #1 Private Tours for up to 6 people Boston Sightseeing Tour - a fully-narrated driving tour Private City Tour of Boston and Cambridge Lexington and Concord 3 hour private car tour from Boston View all Tours with Hotel Pickup →

Q: Got any more Massachusetts trip ideas?

We sure do. Check out our curated lists of hand-picked Massachusetts Tours. Top 10 Massachusetts 2026 Senior-friendly tours Massachusetts The best tours and activities for culture lovers in Massachusetts Top Day Trips from Massachusetts Things to do in Massachusetts this summer View all Massachusetts Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Massachusetts?

Based on our sales data over the past year, the most popular styles of tours and activities in Massachusetts are: Massachusetts Luxury & Special Occasions Massachusetts Luxury Tours Massachusetts Tours & Sightseeing Massachusetts Cultural & Theme Tours Massachusetts Historical & Heritage Tours View all tour styles in Massachusetts →

Private Half-Day Driving Tour of Boston and Cambridge

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. This is a half-day driving tour that takes you …More

Boston, USA

5.0 (7)

Private Half-Day Driving Tour of Boston and Cambridge

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. This is a half-day driving tour that takes you...

4 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$88

Provincetown Self-Guided Walking Audio Tour

Explore Provincetown's rich history with this self-guided walking tour! Discover the charm of Commercial Street, admire the towering Pilgrim Monument, and visit the bustling Beachcombers …More

Cape Cod, USA

4.9 (7)

Provincetown Self-Guided Walking Audio Tour

Explore Provincetown's rich history with this self-guided walking tour! Discover the charm of Commercial Street, admire the towering Pilgrim Monument, and visit the bustling Beachcombers...

1 to 2 hours Free Cancellation

4.9 (7)

from
$15

Plymouth & South Shore Private Tour from Boston

This full day private tour combines some of the best coastal views in the region with Pilgrim history. First stop focuses on the Presidential history …More

Boston, USA

5.0 (6)

Plymouth & South Shore Private Tour from Boston

This full day private tour combines some of the best coastal views in the region with Pilgrim history. First stop focuses on the Presidential history...

6 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$995

Private Walking Tour from Boston to Beacon Hill Freedom Trail Harborwalk

The best tour for the first acquaintance with Boston. Step by step we will become acquainted with the exciting history of the founding of Boston, …More

Boston, USA

5.0 (5)

Private Walking Tour from Boston to Beacon Hill Freedom Trail Harborwalk

The best tour for the first acquaintance with Boston. Step by step we will become acquainted with the exciting history of the founding of Boston,...

3 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$350

Boston Private Day Trip with Salem & Cape Ann’s North Shore

Enjoy the beauty of New England’s coastal towns on a private day trip from Boston, driving along the North Shore to Cape Ann, including Manchester-by-the-Sea, …More

Boston, USA

4.8 (4)

Boston Private Day Trip with Salem & Cape Ann’s North Shore

Enjoy the beauty of New England’s coastal towns on a private day trip from Boston, driving along the North Shore to Cape Ann, including Manchester-by-the-Sea,...

6 hours Hotel pickup offered

4.8 (4)

from
$205

Highlights and History of Boston: GPS Guided Audio Tour

This tour hits the highlights of Boston's most historic districts. You can take this tour anytime between 7:00am and 8:00pm. Once you make the booking, …More

Boston, USA

4.8 (4)

Highlights and History of Boston: GPS Guided Audio Tour

This tour hits the highlights of Boston's most historic districts. You can take this tour anytime between 7:00am and 8:00pm. Once you make the booking,...

3 to 4 hours

4.8 (4)

from
$10

Private Newport Mansions Day Trip from Boston

Enjoy a private, customizable day trip from Boston to Newport in a comfortable vehicle reserved for your group. This is private transportation with flexible sightseeing …More

Boston, USA

5.0 (4)

Private Newport Mansions Day Trip from Boston

Enjoy a private, customizable day trip from Boston to Newport in a comfortable vehicle reserved for your group. This is private transportation with flexible sightseeing...

8 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (4)

from
$1,012

Private Walking Tour of the 100th Town in Westborough

There is a lot to see in this picturesque New England town: authentic houses, churches, cemeteries, farms and more, including dining and shopping. If you …More

5.0 (4)

Private Walking Tour of the 100th Town in Westborough

There is a lot to see in this picturesque New England town: authentic houses, churches, cemeteries, farms and more, including dining and shopping. If you...

1 to 2 hours Free Cancellation

5.0 (4)

from
$40

Salem Witch Trials Driving Tour to See the Real Witch Trial Sites

Explore the chilling history of the Salem Witch Trials on this self guided audio driving tour on our self-guided tour app, which takes you through …More

Salem, USA

4.8 (4)

Salem Witch Trials Driving Tour to See the Real Witch Trial Sites

Explore the chilling history of the Salem Witch Trials on this self guided audio driving tour on our self-guided tour app, which takes you through...

1 to 3 hours Free Cancellation

4.8 (4)

from
$15

Boston Massachusetts Private Photography Tour

We are soulful photographers. Our objective is to create absolutely stunning photographs for you that you will cherish and proudly share with your friends and …More

Boston, USA

5.0 (3)

Boston Massachusetts Private Photography Tour

We are soulful photographers. Our objective is to create absolutely stunning photographs for you that you will cherish and proudly share with your friends and...

1 hour Free Cancellation

5.0 (3)

from
$130

Private Cultural Walk Through Historic Salem’s Legends

This private cultural walking tour reveals the fascinating heritage and enduring mysteries of Salem, one of America’s most historic and storied destinations. Explore the city's …More

Salem, USA

5.0 (3)

Private Cultural Walk Through Historic Salem’s Legends

This private cultural walking tour reveals the fascinating heritage and enduring mysteries of Salem, one of America’s most historic and storied destinations. Explore the city's...

2 hours Free Cancellation

5.0 (3)

from
$299

The Best of Boston: Private Half-Day Highlights Driving Tour

See the best of Boston from one end of the city to the other on this private, half-day driving highlights tour. If you are arriving …More

Boston, USA

5.0 (3)

The Best of Boston: Private Half-Day Highlights Driving Tour

See the best of Boston from one end of the city to the other on this private, half-day driving highlights tour. If you are arriving...

3 hours Hotel pickup offered

5.0 (3)

from
$140

Beyond Boston Freedom Trail: Private Half-Day Walking Tour

Whether this is your first time in Boston or your fiftieth, this tour is the insider’s tour, which will take you through the heart of …More

Boston, USA

5.0 (3)

Beyond Boston Freedom Trail: Private Half-Day Walking Tour

Whether this is your first time in Boston or your fiftieth, this tour is the insider’s tour, which will take you through the heart of...

3 hours Free Cancellation

5.0 (3)

from
$45

Cambridge, Lexington, & Concord: Private Revolutionary War Tour

Immerse yourself in this Revolutionary War full-day driving tour which will take you on a journey to explore the significant sites of the American Revolution. …More

Boston, USA

5.0 (2)

Cambridge, Lexington, & Concord: Private Revolutionary War Tour

Immerse yourself in this Revolutionary War full-day driving tour which will take you on a journey to explore the significant sites of the American Revolution....

6 hours Hotel pickup offered

5.0 (2)

from
$160

Boston Freedom Trail Self-Guided Audio Tour

Walk in the footsteps of America’s revolutionaries with our immersive Boston Freedom Trail audio tour! Unlike crowded tours, this guide brings history to life at …More

Boston, USA

5.0 (2)

Boston Freedom Trail Self-Guided Audio Tour

Walk in the footsteps of America’s revolutionaries with our immersive Boston Freedom Trail audio tour! Unlike crowded tours, this guide brings history to life at...

2 days Free Cancellation

5.0 (2)

from
$10

Private Tour of Boston for Families & Kids

Spend a great day in Boston learning about history and exploring all the top attractions! The tour is designed to be fun for the whole …More

Boston, USA

5.0 (2)

Private Tour of Boston for Families & Kids

Spend a great day in Boston learning about history and exploring all the top attractions! The tour is designed to be fun for the whole...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$104

Boston Civil War and Abolition Movement: A Self-Guided Audio Tour

Are you looking for a way to discover Boston without joining a tour group? Explore at your own pace with this self-guided walking tour. • …More

Boston, USA

5.0 (2)

Boston Civil War and Abolition Movement: A Self-Guided Audio Tour

Are you looking for a way to discover Boston without joining a tour group? Explore at your own pace with this self-guided walking tour. •...

90 to 120 minutes

5.0 (2)

from
$12

Private Luxury Helicopter Flight Over Boston with Hotel Pick-Up

Step into the spotlight of an exclusive cinematic adventure with our Luxury VIP Flight over the mesmerizing backdrop of Boston. This isn't just a tour; …More

Boston, USA

5.0 (2)

Private Luxury Helicopter Flight Over Boston with Hotel Pick-Up

Step into the spotlight of an exclusive cinematic adventure with our Luxury VIP Flight over the mesmerizing backdrop of Boston. This isn't just a tour;...

1 to 2 hours Free Cancellation

5.0 (2)

from
$699

Harvard's Haunts Solo Smart Phone Guided App Ghost Walking Tour

Welcome to Harvard’s Famous Haunts Walking Tour, where we journey through the historic and eerie corners of the oldest university in America. Go at your …More

Cambridge, USA

5.0 (2)

Harvard's Haunts Solo Smart Phone Guided App Ghost Walking Tour

Welcome to Harvard’s Famous Haunts Walking Tour, where we journey through the historic and eerie corners of the oldest university in America. Go at your...

50 to 60 minutes Free Cancellation

5.0 (2)

from
$8

Private Walking Tour with a Local Guide in Boston

Boston can sometimes feel inaccessible to foreign visitors. Take the mystery out of your visit by exploring with a local on a private walking tour. …More

Boston, USA

5.0 (2)

Private Walking Tour with a Local Guide in Boston

Boston can sometimes feel inaccessible to foreign visitors. Take the mystery out of your visit by exploring with a local on a private walking tour....

3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$75

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Massachusetts Private Sightseeing Tours?

What are the best kid-friendly options for Massachusetts Private Sightseeing Tours Tours?

Which Massachusetts Private Sightseeing Tours have Instant Confirmation?

Massachusetts Private Sightseeing Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Massachusetts Private Sightseeing Tours have Free Cancellation?

Massachusetts Private Sightseeing Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Massachusetts Private Sightseeing Tours have Hotel Pickup?

Got any more Massachusetts trip ideas?

What are the most popular styles of Tours and Activities in Massachusetts?