Top Massachusetts Private Sightseeing 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 →

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

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

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

App-Guided "Historic Boston Downtown Freedom Trail" Walking Tour

Dig Deeper into Downtown Boston's historical sites between the Boston Common Visitors Center and Blackstone Corner at your own pace and schedule on this location …More

Boston, USA

4.3 (24)

App-Guided "Historic Boston Downtown Freedom Trail" Walking Tour

Dig Deeper into Downtown Boston's historical sites between the Boston Common Visitors Center and Blackstone Corner at your own pace and schedule on this location...

50 to 100 minutes Free Cancellation

4.3 (24)

from
$5

Boston’s Freedom Trail: A Self-Guided Audio Tour

Go beyond Revolutionary War history books with this affordable walking tour in Boston. • Take in important historical landmarks like the Boston Common which was …More

Boston, USA

4.1 (17)

Boston’s Freedom Trail: A Self-Guided Audio Tour

Go beyond Revolutionary War history books with this affordable walking tour in Boston. • Take in important historical landmarks like the Boston Common which was...

75 to 90 minutes

4.1 (17)

from
$10

Nantucket Self-Guided Audio Walking Tour: Beyond the Cobblestones

Explore historic downtown Nantucket on a self-guided audio walking tour. Follow a roughly 2-mile route as stories and directions play automatically along the way. Hear …More

Nantucket, USA

4.2 (11)

Nantucket Self-Guided Audio Walking Tour: Beyond the Cobblestones

Explore historic downtown Nantucket on a self-guided audio walking tour. Follow a roughly 2-mile route as stories and directions play automatically along the way. Hear...

2 to 3 hours Free Cancellation

4.2 (11)

from
$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 …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 to Coastal Maine Private Day Trip

Take a break from the city and head north to explore beautiful, coastal Maine. With this private, full-day trip you'll enjoy roundtrip transportation with a private …More

Boston, USA

4.2 (9)

Boston to Coastal Maine Private Day Trip

Take a break from the city and head north to explore beautiful, coastal Maine. With this private, full-day trip you'll enjoy roundtrip transportation with a private...

10 hours Hotel pickup offered Free Cancellation

4.2 (9)

from
$1,200

Self Guided Driving Tour Battle of Lexington and Concord

Explore the pivotal sites of the American Revolution on this self-guided driving tour of Lexington and Concord. Follow the historic Battle Road where the first …More

Boston, USA

3.9 (8)

Self Guided Driving Tour Battle of Lexington and Concord

Explore the pivotal sites of the American Revolution on this self-guided driving tour of Lexington and Concord. Follow the historic Battle Road where the first...

60 to 90 minutes Free Cancellation

3.9 (8)

from
$10

Boston Record Breakers: Self-Guided Scavenger Hunt

Learn about Boston’s rich history and its standing in the U.S history of being “first in the nation” to build and enact many things. You’ll …More

Boston, USA

4.0 (5)

Boston Record Breakers: Self-Guided Scavenger Hunt

Learn about Boston’s rich history and its standing in the U.S history of being “first in the nation” to build and enact many things. You’ll...

1 hour 20 minutes Free Cancellation

4.0 (5)

from
$6

Self-Guided Audio Tour of Boston North End

Discover the North End, Little Italy's history, Paul Revere, Italian Food, immigration history of the Italians, Irish, Jewish and Africans on this Smart Phone navigated, …More

Boston, USA

4.2 (5)

Self-Guided Audio Tour of Boston North End

Discover the North End, Little Italy's history, Paul Revere, Italian Food, immigration history of the Italians, Irish, Jewish and Africans on this Smart Phone navigated,...

50 to 60 minutes Free Cancellation

4.2 (5)

from
$6

Self-Guided Salem Witch Trials Walking Audio Tour

Download GuideAlong's walking tour of Salem to explore the infamous Salem Witch Trials. Along the 1.5-mile route, we’ll point out important locations and share local …More

Salem, USA

4.2 (5)

Self-Guided Salem Witch Trials Walking Audio Tour

Download GuideAlong's walking tour of Salem to explore the infamous Salem Witch Trials. Along the 1.5-mile route, we’ll point out important locations and share local...

2 to 3 hours Free Cancellation

4.2 (5)

from
$13

Harvard’s Secret Society: Exploration Game and Tour

Discover iconic locations from Harvard Yard by solving clues and unlocking stories on your phone. Play the engaging exploration game, reenacting the story of Owen …More

Cambridge, USA

4.0 (3)

Harvard’s Secret Society: Exploration Game and Tour

Discover iconic locations from Harvard Yard by solving clues and unlocking stories on your phone. Play the engaging exploration game, reenacting the story of Owen...

80 to 110 minutes Free Cancellation

4.0 (3)

from
$6

Haunted Salem: Witch Trials and Ghosts Tour

Walk Salem’s dark past under moonlit streets and learn true stories of witch trials, haunted houses, and restless spirits. A clear, friendly voice leads you …More

Salem, USA

4.0 (3)

Haunted Salem: Witch Trials and Ghosts Tour

Walk Salem’s dark past under moonlit streets and learn true stories of witch trials, haunted houses, and restless spirits. A clear, friendly voice leads you...

1 to 3 hours Free Cancellation

4.0 (3)

from
$10

Cape Ann Self Guided Driving Tour Audio/GPS Gloucester, Rockport

Explore the coastline of Gloucester and Rockport, Massachusetts, with this self-guided GPS audio driving tour of Cape Ann. Discover the rich history of Cape Ann …More

Gloucester, USA

4.0 (2)

Cape Ann Self Guided Driving Tour Audio/GPS Gloucester, Rockport

Explore the coastline of Gloucester and Rockport, Massachusetts, with this self-guided GPS audio driving tour of Cape Ann. Discover the rich history of Cape Ann...

2 to 4 hours Free Cancellation

4.0 (2)

from
$12

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

Boston to Woods Hole & Martha's Vineyard Ferry Private Chauffeur Service

Door-to-door Boston to Woods Hole Martha's Vineyard Ferry "flat rate" service is easy and affordable. Forget about dealing with traffic and paying for parking, when …More

Boston, USA

4.0 (1)

Boston to Woods Hole & Martha's Vineyard Ferry Private Chauffeur Service

Door-to-door Boston to Woods Hole Martha's Vineyard Ferry "flat rate" service is easy and affordable. Forget about dealing with traffic and paying for parking, when...

2 hours 45 minutes Hotel pickup offered Free Cancellation

4.0 (1)

from
$525

Plymouth Pilgrim Historic Self Guided GPS Audio Walking Tour

The tour will take you from the decks of the Mayflower Two, a faithful replica of the Pilgrims’ ship, and end at the historic Jabez …More

Plymouth, USA

3.6 (8)

Plymouth Pilgrim Historic Self Guided GPS Audio Walking Tour

The tour will take you from the decks of the Mayflower Two, a faithful replica of the Pilgrims’ ship, and end at the historic Jabez...

60 to 90 minutes Free Cancellation

3.6 (8)

from
$10

Oak Bluffs, Martha's Vineyard Audio Tour

Knockabout Travel takes you to Martha's Vineyard, with this self-paced audio tour of the most popular town on the island. Discover the origin story of …More

Martha's Vineyard, USA

3.6 (7)

Oak Bluffs, Martha's Vineyard Audio Tour

Knockabout Travel takes you to Martha's Vineyard, with this self-paced audio tour of the most popular town on the island. Discover the origin story of...

60 to 90 minutes

3.6 (7)

from
$13

The Ghosts of Boston's Past Haunted Self-guided Tour

This an on demand, smart phone guided haunted walking tour in Boston. Go to 10 1/2 Beacon Street, press play and put your phone in …More

Boston, USA

3.5 (4)

The Ghosts of Boston's Past Haunted Self-guided Tour

This an on demand, smart phone guided haunted walking tour in Boston. Go to 10 1/2 Beacon Street, press play and put your phone in...

30 to 45 minutes Free Cancellation

3.5 (4)

from
$5

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?

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?