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: Salem half day private tour from Boston Plymouth Half Day Private Tour from Boston Plymouth & South Shore Private Tour from Boston Private Tour of Lexington, Concord, and Boston 30-Min Private Helicopter Skyline Tour of 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 →

Explore the gas lit winter wonderland streets of Boston and Beacon Hill as we discover the Christmas tales of Boston's past walking on cobbled stoned …More

Boston, USA

5.0 (2)

Self-Guided Boston Christmas Tour

Explore the gas lit winter wonderland streets of Boston and Beacon Hill as we discover the Christmas tales of Boston's past walking on cobbled stoned...

40 to 50 minutes Free Cancellation

5.0 (2)

from
$10

Local Bostonian and Historical Driving Tours

We provide exciting private tours of all the historical sites in Boston that includes background for various neighborhoods and historical perspectives. …More

Boston, USA

5.0 (2)

Local Bostonian and Historical Driving Tours

We provide exciting private tours of all the historical sites in Boston that includes background for various neighborhoods and historical perspectives....

1 to 3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$600

Private Culinary Walking Tour in Boston Historic Districts

This private culinary walking tour introduces Boston’s historic districts through authentic regional flavors. You begin in the Blackstone Block where narrow streets reflect early commercial …More

Boston, USA

5.0 (1)

Private Culinary Walking Tour in Boston Historic Districts

This private culinary walking tour introduces Boston’s historic districts through authentic regional flavors. You begin in the Blackstone Block where narrow streets reflect early commercial...

3 hours Free Cancellation

5.0 (1)

from
$328

We'll see the sights on Boston's Freedom Trail and get a closer look by leaving the car and walking inside some locations (depends on day …More

Boston, USA

5.0 (1)

Boston Freedom Trail Private Car Tour

We'll see the sights on Boston's Freedom Trail and get a closer look by leaving the car and walking inside some locations (depends on day...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$600

In this immersive 4-hour experience, we will discover the best of Both Worlds: Historic Boston and Harvard University. While we explore the legendary Freedom Trail, …More

Boston, USA

5.0 (1)

Boston Harvard Half Day Tour

In this immersive 4-hour experience, we will discover the best of Both Worlds: Historic Boston and Harvard University. While we explore the legendary Freedom Trail,...

4 hours Free Cancellation

5.0 (1)

from
$425

Cambridge Classics Harvard MIT and Everything In Between

Experience the pinnacle of global intelligence on this sophisticated journey through Harvard University and MIT. We’ll walk the hallowed paths of Harvard Yard, touching the …More

Cambridge, USA

5.0 (1)

Cambridge Classics Harvard MIT and Everything In Between

Experience the pinnacle of global intelligence on this sophisticated journey through Harvard University and MIT. We’ll walk the hallowed paths of Harvard Yard, touching the...

4 hours Free Cancellation

5.0 (1)

from
$450

Private Full Day Tour to Coastal Maine from Boston with Hotel pick-up

Enjoy this private full day tour with your own private driver and official tour guide and explore the vibrant coast of Maine. Get ready to …More

Boston, USA

5.0 (1)

Private Full Day Tour to Coastal Maine from Boston with Hotel pick-up

Enjoy this private full day tour with your own private driver and official tour guide and explore the vibrant coast of Maine. Get ready to...

10 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$364

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

Full-Day Private Tour of Boston with Pick Up

For this private tour of Boston, let us take you to all the emblematic sites of the city. Also, enjoy a view of the famous …More

Boston, USA

5.0 (1)

Full-Day Private Tour of Boston with Pick Up

For this private tour of Boston, let us take you to all the emblematic sites of the city. Also, enjoy a view of the famous...

6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$329

French-American Guided Tour of the Freedom Trail, Boston

Follow a professional historian, concerned about historical accuracy, able to address adults and children alike, in joy and good humor, to discuss the links between …More

Boston, USA

5.0 (1)

French-American Guided Tour of the Freedom Trail, Boston

Follow a professional historian, concerned about historical accuracy, able to address adults and children alike, in joy and good humor, to discuss the links between...

90 to 120 minutes Free Cancellation

5.0 (1)

from
$85

Private Historical Walking Tour in Boston Cultural Landmarks

This private historical walking tour reveals Boston’s cultural and architectural legacy. You begin along the Greenway where modern design meets the path of early trade …More

Boston, USA

5.0 (1)

Private Historical Walking Tour in Boston Cultural Landmarks

This private historical walking tour reveals Boston’s cultural and architectural legacy. You begin along the Greenway where modern design meets the path of early trade...

2 hours Free Cancellation

5.0 (1)

from
$178

Cruise - Sightsee - Foliage in Boston, on Private Yacht Trinacria

Join Captain Riccardo aboard the Trinacria for a Private tour of Boston Harbor & The Harbor Islands. Choices include Sightseeing, Foliage Tours in Autumn or …More

Boston, USA

5.0 (1)

Cruise - Sightsee - Foliage in Boston, on Private Yacht Trinacria

Join Captain Riccardo aboard the Trinacria for a Private tour of Boston Harbor & The Harbor Islands. Choices include Sightseeing, Foliage Tours in Autumn or...

3 to 5 hours Hotel pickup offered

5.0 (1)

from
$2,000

Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

Witness the breathtaking Boston Harbor skyline and many landmarks from the unique perspective of the harbor. We are one of the only Private Sunset Cruises …More

Boston, USA

5.0 (1)

Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

Witness the breathtaking Boston Harbor skyline and many landmarks from the unique perspective of the harbor. We are one of the only Private Sunset Cruises...

2 hours

5.0 (1)

from
$1,200

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

Discover Boston's revolutionary spirit and rich heritage through an immersive audio experience that puts you in complete control of your journey. Unlike crowded group tours …More

Boston, USA

5.0 (1)

Boston Self Guided Audio Experience

Discover Boston's revolutionary spirit and rich heritage through an immersive audio experience that puts you in complete control of your journey. Unlike crowded group tours...

3 to 9 hours

5.0 (1)

from
$6

Self Guided Walking Tour of Oak Bluffs Marthas Vineyard

Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come …More

Martha's Vineyard, USA

5.0 (1)

Self Guided Walking Tour of Oak Bluffs Marthas Vineyard

Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come...

2 to 3 hours Free Cancellation

5.0 (1)

from
$10

Moby Dick's New Bedford Smartphone Guided Walking Tour

Herman Melville said this city was perhaps the dearest place to live in, in all of New England. On this tour you will explore the …More

Cape Cod, USA

5.0 (1)

Moby Dick's New Bedford Smartphone Guided Walking Tour

Herman Melville said this city was perhaps the dearest place to live in, in all of New England. On this tour you will explore the...

50 to 70 minutes Free Cancellation

5.0 (1)

from
$8

Sit back and relax while you enjoy a personalized tour of Boston's best sites from the comfort of a pedicab. See Freedom Trail sites without …More

Boston, USA

5.0 (1)

Customizable Pedicab Tours in Boston

Sit back and relax while you enjoy a personalized tour of Boston's best sites from the comfort of a pedicab. See Freedom Trail sites without...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$135

Martha's Vineyard at Your Pace: Iconic Cottages & Lighthouses

Welcome to Martha's Vineyard, the storied island off Cape Cod that has captivated visitors for generations with its windswept beaches and fiercely independent spirit. This …More

Martha's Vineyard, USA

5.0 (1)

Martha's Vineyard at Your Pace: Iconic Cottages & Lighthouses

Welcome to Martha's Vineyard, the storied island off Cape Cod that has captivated visitors for generations with its windswept beaches and fiercely independent spirit. This...

8 hours Free Cancellation

5.0 (1)

from
$5

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 (1)

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 (1)

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?