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: Highlights and History of Boston: GPS Guided Audio Tour Boston’s Freedom Trail: A Self-Guided Audio Tour Private Newport Mansions Day Trip from Boston Private Walking Tour of the 100th Town in Westborough Boston Civil War and Abolition Movement: A Self-Guided Audio Tour

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 →

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

Discover Boston's Revolutionary history on this Classic Freedom Trail Walking Tour including Historic Downtown Boston, the North End and Charlestown. -Go anytime, at your own …More

Boston, USA

4.4 (291)

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

Discover Boston's Revolutionary history on this Classic Freedom Trail Walking Tour including Historic Downtown Boston, the North End and Charlestown. -Go anytime, at your own...

2 to 3 hours Free Cancellation

4.4 (291)

from
$8

Self-Guided Smartphone Ghost Walking Tour in Salem

This is a Smartphone Guided ghost tour on our walking tour app. Go to the Ropes Mansion, press play and put your phone in your …More

Salem, USA

4.3 (253)

Self-Guided Smartphone Ghost Walking Tour in Salem

This is a Smartphone Guided ghost tour on our walking tour app. Go to the Ropes Mansion, press play and put your phone in your...

40 to 50 minutes Free Cancellation

4.3 (253)

from
$8

Boston Freedom Trail Self-Guided Tour with Audio Narration & Map

Walk in the footsteps of Revolutionary War heroes with this self-guided audio tour of Boston’s Freedom Trail! Get the facts behind the story of Paul …More

Boston, USA

4.5 (118)

Boston Freedom Trail Self-Guided Tour with Audio Narration & Map

Walk in the footsteps of Revolutionary War heroes with this self-guided audio tour of Boston’s Freedom Trail! Get the facts behind the story of Paul...

3 to 4 hours Free Cancellation

4.5 (118)

from
$10

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

Ultimate Historic Salem and Witch Trials Self-Guided Walking Tour

Uncover the truth behind the infamous Salem Witch Trials with this self-guided walking tour of Salem, Massachusetts! See Salem Armory, the Old Burying Point Cemetery, …More

Salem, USA

4.3 (78)

Ultimate Historic Salem and Witch Trials Self-Guided Walking Tour

Uncover the truth behind the infamous Salem Witch Trials with this self-guided walking tour of Salem, Massachusetts! See Salem Armory, the Old Burying Point Cemetery,...

1 to 2 hours Free Cancellation

4.3 (78)

from
$14

Discover Boston and Cambridge on a private six-hour sightseeing experience designed around your group’s interests. Travel in a comfortable private vehicle while your knowledgeable driver-guide …More

Boston, USA

4.7 (66)

Boston Private City Tour

Discover Boston and Cambridge on a private six-hour sightseeing experience designed around your group’s interests. Travel in a comfortable private vehicle while your knowledgeable driver-guide...

6 hours Hotel pickup offered Free Cancellation

4.7 (66)

from
$925

Boston's Beacon Hill Underground Railroad Audio Walking Tour

Discover Beacon Hill's Underground Railroad history while walking its cobbled stones streets. On this historic adventure you'll see the old hidden alley's slave catchers once …More

Boston, USA

4.7 (30)

Boston's Beacon Hill Underground Railroad Audio Walking Tour

Discover Beacon Hill's Underground Railroad history while walking its cobbled stones streets. On this historic adventure you'll see the old hidden alley's slave catchers once...

45 to 55 minutes Free Cancellation

4.7 (30)

from
$10

Private Open-Air Pedicab Tour in Provincetown

See the best of Provincetown in a short amount of time with a knowledgeable local guide who lives here year-round. This tour combines scenic views, …More

Cape Cod, USA

4.5 (24)

Private Open-Air Pedicab Tour in Provincetown

See the best of Provincetown in a short amount of time with a knowledgeable local guide who lives here year-round. This tour combines scenic views,...

60 to 90 minutes Hotel pickup offered Free Cancellation

4.5 (24)

from
$117

Boston Harborwalk & Tea Party Self-Guided Walking Audio Tour

This is not a ticket to attractions along the route. Immerse yourself in the stories of the American Revolution, Boston Tea Party, and Sons of …More

Boston, USA

4.7 (19)

Boston Harborwalk & Tea Party Self-Guided Walking Audio Tour

This is not a ticket to attractions along the route. Immerse yourself in the stories of the American Revolution, Boston Tea Party, and Sons of...

2 to 3 hours Free Cancellation

4.7 (19)

from
$10

Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour

Go at your own pace, anytime! It's your tour. On our historic walking tour of the Edgartown, you will see the iconic sights and secret …More

Martha's Vineyard, USA

4.3 (15)

Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour

Go at your own pace, anytime! It's your tour. On our historic walking tour of the Edgartown, you will see the iconic sights and secret...

60 to 75 minutes Free Cancellation

4.3 (15)

from
$10

Boston Walk Through History Private & All-Inclusive Tour

Our Boston Walk Through History Tour will take you to the most historic spots in Boston in one day. If you are looking for a …More

Boston, USA

4.6 (11)

Boston Walk Through History Private & All-Inclusive Tour

Our Boston Walk Through History Tour will take you to the most historic spots in Boston in one day. If you are looking for a...

3 to 6 hours Free Cancellation

4.6 (11)

from
$339

Plymouth Half Day Private Tour from Boston

If you've always wanted to see Plymouth Rock, this 4 hour tour lets you check it off the bucket list. It can fit snuggly into …More

Boston, USA

4.6 (10)

Plymouth Half Day Private Tour from Boston

If you've always wanted to see Plymouth Rock, this 4 hour tour lets you check it off the bucket list. It can fit snuggly into...

4 hours Hotel pickup offered Free Cancellation

4.6 (10)

from
$695

Private All-Inclusive Boston Famous Foodie Tour

Our Boston Food Tour will take you to the most iconic and delicious spots in Boston all in one day. If you are looking for …More

Boston, USA

4.7 (10)

Private All-Inclusive Boston Famous Foodie Tour

Our Boston Food Tour will take you to the most iconic and delicious spots in Boston all in one day. If you are looking for...

3 hours Free Cancellation

4.7 (10)

from
$288

North End Boston Mafia Exploration Game and Tour

Discover Boston’s Mafia past by solving challenges and unlocking stories on your phone, leading you to new places and amazing stories. Play our engaging exploration …More

Boston, USA

4.3 (10)

North End Boston Mafia Exploration Game and Tour

Discover Boston’s Mafia past by solving challenges and unlocking stories on your phone, leading you to new places and amazing stories. Play our engaging exploration...

130 to 160 minutes Free Cancellation

4.3 (10)

from
$7

Wellfleet Harbor Seal Cruise Small Group Boat Tour on Cape Cod

Enjoy a private seal-watching crossing with only your group aboard. We’ll explore at a relaxed pace, with time to linger when conditions allow and observe …More

Cape Cod, USA

4.6 (7)

Wellfleet Harbor Seal Cruise Small Group Boat Tour on Cape Cod

Enjoy a private seal-watching crossing with only your group aboard. We’ll explore at a relaxed pace, with time to linger when conditions allow and observe...

1 hour Free Cancellation

4.6 (7)

from
$400

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

Self-Guided Smartphone Ghost Walking Tour Boston App EMF Reader

This is a Smartphone Guided ghost tour on our walking tour app. Go to the 10 1/2 Beacon St, press play and put your phone …More

Boston, USA

4.5 (6)

Self-Guided Smartphone Ghost Walking Tour Boston App EMF Reader

This is a Smartphone Guided ghost tour on our walking tour app. Go to the 10 1/2 Beacon St, press play and put your phone...

30 to 45 minutes Free Cancellation

4.5 (6)

from
$10

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

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

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

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?