Top Massachusetts Private Sightseeing Tours

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 →

Boston’s Freedom Trail: Private Tour including Paul Revere House

Visit the best of Boston on a half-day tour, discovering the best of the Freedom Trail on your private tour of Boston’s highlights. Along your …More

Boston, USA

3.0 (1)

Boston’s Freedom Trail: Private Tour including Paul Revere House

Visit the best of Boston on a half-day tour, discovering the best of the Freedom Trail on your private tour of Boston’s highlights. Along your...

3 hours Free Cancellation

3.0 (1)

from
$65

Interactive Mystery Scavenger Hunt in Boston

Channel your inner Sherlock Holmes in this mystery scavenger hunt around Boston! In "Murder by Boston Common," you are transported back to the year 1895. …More

Boston, USA

5.0 (1)

Interactive Mystery Scavenger Hunt in Boston

Channel your inner Sherlock Holmes in this mystery scavenger hunt around Boston! In "Murder by Boston Common," you are transported back to the year 1895....

1 to 2 hours Free Cancellation

5.0 (1)

from
$59

Private Walking Tour of Freedom Trail and Little Italy

See every site on the Freedom Trail! This walking tour includes all 16 stops on the Freedom Trail, covering historical sites such as the Paul …More

Boston, USA

5.0 (8)

Private Walking Tour of Freedom Trail and Little Italy

See every site on the Freedom Trail! This walking tour includes all 16 stops on the Freedom Trail, covering historical sites such as the Paul...

4 hours 30 minutes Free Cancellation

5.0 (8)

from
$53

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

Get the full Massachusetts experience with this combo of walking and driving tours around Boston! You’ll find ten tours in one app - all highly …More

Gloucester, USA

4.7 (3)

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

Get the full Massachusetts experience with this combo of walking and driving tours around Boston! You’ll find ten tours in one app - all highly...

2 days Free Cancellation

4.7 (3)

from
$50

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

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

Cape Cod & Provincetown Self-Guided Driving & Walking Audio Tour

Purchase one tour per car, not per person. Everyone listens together! Explore all that Cape Cod has to offer with this self-guided driving tour, from …More

Cape Cod, USA

4.1 (208)

Cape Cod & Provincetown Self-Guided Driving & Walking Audio Tour

Purchase one tour per car, not per person. Everyone listens together! Explore all that Cape Cod has to offer with this self-guided driving tour, from...

3 to 4 hours Free Cancellation

4.1 (208)

from
$25

Boston App-Guided Audio Tour Bundle: Freedom Trail and More

Explore Boston, Cambridge, Salem, Cape Ann, and more! This package covers Boston's iconic Freedom Trail (Old North Church, Faneuil Hall, & more), the Harborwalk, Salem …More

Gloucester, USA

4.3 (6)

Boston App-Guided Audio Tour Bundle: Freedom Trail and More

Explore Boston, Cambridge, Salem, Cape Ann, and more! This package covers Boston's iconic Freedom Trail (Old North Church, Faneuil Hall, & more), the Harborwalk, Salem...

6 to 8 hours Free Cancellation

4.3 (6)

from
$25

Freedom Trail and Salem Witch Trials App-Guided Audio Tour

Dive into New England history with this tour combo of Salem and the Boston Freedom Trail. In Salem, uncover the truth behind the Witch Trials. …More

Salem, USA

5.0 (2)

Freedom Trail and Salem Witch Trials App-Guided Audio Tour

Dive into New England history with this tour combo of Salem and the Boston Freedom Trail. In Salem, uncover the truth behind the Witch Trials....

2 to 4 hours Free Cancellation

5.0 (2)

from
$25

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Recommended: Purchase one tour per car, not per person. Everyone listens together! Discover the natural beauty of New England’s most picturesque coastline with this narrated …More

Gloucester, USA

4.3 (112)

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Recommended: Purchase one tour per car, not per person. Everyone listens together! Discover the natural beauty of New England’s most picturesque coastline with this narrated...

2 to 3 hours Free Cancellation

4.3 (112)

from
$17

Explore Cape Cod’s scenic beauty with this self-guided driving tour. Visit the Cape Cod Visitor Center, then ascend Scargo Tower for breathtaking views. Discover Harwich …More

Cape Cod, USA

3.9 (32)

Cape Cod Self-Guided Driving Audio Tour

Explore Cape Cod’s scenic beauty with this self-guided driving tour. Visit the Cape Cod Visitor Center, then ascend Scargo Tower for breathtaking views. Discover Harwich...

3 to 4 hours Free Cancellation

3.9 (32)

from
$17

Download GuideAlong's Cape Cod audio tour to discover what “summer” really means. Drive the iconic “bent arm” between Barnstable and Provincetown, with side trips to …More

Cape Cod, USA

4.3 (3)

Self Guided Driving Audio Tour Cape Cod

Download GuideAlong's Cape Cod audio tour to discover what “summer” really means. Drive the iconic “bent arm” between Barnstable and Provincetown, with side trips to...

4 to 5 hours Free Cancellation

4.3 (3)

from
$17

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

Lexington & Concord Self-Guided Driving & Walking Audio Tour

Discover the thrilling events behind the “shot heard ‘round the world” with this self-guided driving/walking tour through Lexington and Concord. Follow the path of the …More

4.2 (73)

Lexington & Concord Self-Guided Driving & Walking Audio Tour

Discover the thrilling events behind the “shot heard ‘round the world” with this self-guided driving/walking tour through Lexington and Concord. Follow the path of the...

2 to 3 hours Free Cancellation

4.2 (73)

from
$15

Martha’s Vineyard Self-Guided Driving & Walking Audio Tour

Get ready to visit one of the greatest vacation spots in the USA, a favorite among celebrities and even presidents! Martha’s Vineyard is home to …More

Martha's Vineyard, USA

4.0 (10)

Martha’s Vineyard Self-Guided Driving & Walking Audio Tour

Get ready to visit one of the greatest vacation spots in the USA, a favorite among celebrities and even presidents! Martha’s Vineyard is home to...

2 to 3 hours Free Cancellation

4.0 (10)

from
$15

Boston's Freedom Trail: A Self-Guided Tour of All 16 Sites

Are you looking for a way to see all 16 Freedom Trail sites without joining a tour group? Explore at your own pace with this …More

Boston, USA

4.9 (16)

Boston's Freedom Trail: A Self-Guided Tour of All 16 Sites

Are you looking for a way to see all 16 Freedom Trail sites without joining a tour group? Explore at your own pace with this...

120 to 160 minutes

4.9 (16)

from
$15

Plymouth Pilgrims Self-Guided Walking Audio Tour

Visit the place where the Pilgrims landed! As one of the earliest English settlements in North America, Plymouth is an essential stop for any history …More

Plymouth, USA

4.1 (31)

Plymouth Pilgrims Self-Guided Walking Audio Tour

Visit the place where the Pilgrims landed! As one of the earliest English settlements in North America, Plymouth is an essential stop for any history...

2 to 3 hours Free Cancellation

4.1 (31)

from
$15

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

Boston Haunted History Self-Guided Walking Audio Tour

Traverse Boston’s oldest neighborhoods and hear about the lost souls still trapped within—from the poor, perpetually burning victims of a gas explosion in Boylston Station …More

Boston, USA

5.0 (1)

Boston Haunted History Self-Guided Walking Audio Tour

Traverse Boston’s oldest neighborhoods and hear about the lost souls still trapped within—from the poor, perpetually burning victims of a gas explosion in Boylston Station...

1 to 2 hours Free Cancellation

5.0 (1)

from
$15

Mohawk Trail Scenic Byway Self Guided Audio Driving Tour

The Mohawk Trail Scenic Byway offers a captivating journey through the history and natural beauty of western Massachusetts. This self-guided driving tour allows travelers to …More

4.0 (1)

Mohawk Trail Scenic Byway Self Guided Audio Driving Tour

The Mohawk Trail Scenic Byway offers a captivating journey through the history and natural beauty of western Massachusetts. This self-guided driving tour allows travelers to...

2 to 4 hours Free Cancellation

4.0 (1)

from
$15

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?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Massachusetts Private Sightseeing Tours are:

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:

View all kid-friendly 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?

No problem. These Massachusetts Private Sightseeing Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Massachusetts trip ideas?

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