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 →

Private Walking tour of Boston's Freedom Trail and more!

There are many Freedom Trail tour options in Boston, but why be shuttled on a trolley tour or be limited by the route of a …More

Boston, USA

4.9 (35)

Private Walking tour of Boston's Freedom Trail and more!

There are many Freedom Trail tour options in Boston, but why be shuttled on a trolley tour or be limited by the route of a...

3 hours

4.9 (35)

from
$395

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

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

30-Min Private Helicopter Skyline Tour of Boston

Experience the epitome of luxury with our private helicopter tour of Boston. Discover a world of wonder as you soar above the ever-evolving skyline and …More

Boston, USA

5.0 (7)

30-Min Private Helicopter Skyline Tour of Boston

Experience the epitome of luxury with our private helicopter tour of Boston. Discover a world of wonder as you soar above the ever-evolving skyline and...

1 hour Free Cancellation

5.0 (7)

from
$349

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

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

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

Private tour to northern Massachusetts coast from Boston - Hotel pick up

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

Boston, USA

Private tour to northern Massachusetts coast from Boston - Hotel pick up

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

8 hours Hotel pickup offered Free Cancellation

from
$315

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

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

Boston Private City Tour 4 hours and Harvard University

Enjoy this private half day tour with your own private driver and official tour guide and explore the vibrant city of Boston. Get ready to …More

Boston, USA

3.7 (3)

Boston Private City Tour 4 hours and Harvard University

Enjoy this private half day tour with your own private driver and official tour guide and explore the vibrant city of Boston. Get ready to...

4 hours Hotel pickup offered Free Cancellation

3.7 (3)

from
$234

Private Historical Walking Tour in Boston Freedom Trail

This private historical walking tour reveals Boston’s colonial heritage. You walk a path shaped by revolution and early American ideals. At the Shaw Memorial, honor …More

Boston, USA

Private Historical Walking Tour in Boston Freedom Trail

This private historical walking tour reveals Boston’s colonial heritage. You walk a path shaped by revolution and early American ideals. At the Shaw Memorial, honor...

2 hours Free Cancellation

from
$229

Private Charter Day Sail For up to 6 People

Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to …More

Salem, USA

5.0 (7)

Private Charter Day Sail For up to 6 People

Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to...

1 hour 30 minutes Free Cancellation

5.0 (7)

from
$225

Boston Private Food and History Tour With Revolutionary Sites

Boston's best food and history are scattered across its neighborhoods, so we bring them together in one relaxed, private tour. Start in the North End …More

Boston, USA

5.0 (10)

Boston Private Food and History Tour With Revolutionary Sites

Boston's best food and history are scattered across its neighborhoods, so we bring them together in one relaxed, private tour. Start in the North End...

5 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (10)

from
$213

Visit Historic Concord on a Private Day Trip from Boston

From its revolutionary history to its literary history, Concord is a must-see for any history or literary buff and a perfect day trip idea from …More

Boston, USA

5.0 (10)

Visit Historic Concord on a Private Day Trip from Boston

From its revolutionary history to its literary history, Concord is a must-see for any history or literary buff and a perfect day trip idea from...

5 hours Hotel pickup offered Free Cancellation

5.0 (10)

from
$205

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

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
$179

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 Private Food Tour with 6+ Authentic Tastings

Discover Boston’s famous North End, where Italian tradition meets New England seafood, on our Secret Food Tour. Over 3 delicious hours, our local guide will …More

Boston, USA

5.0 (181)

Boston Private Food Tour with 6+ Authentic Tastings

Discover Boston’s famous North End, where Italian tradition meets New England seafood, on our Secret Food Tour. Over 3 delicious hours, our local guide will...

3 hours

5.0 (181)

from
$160

Private Day Trip to Salem and Hammond Castle from Boston

Enjoy a unique day trip to Boston's northern shore, combining Salem and Hammond Castle! Start the day with a pickup at your door and a …More

Boston, USA

4.8 (17)

Private Day Trip to Salem and Hammond Castle from Boston

Enjoy a unique day trip to Boston's northern shore, combining Salem and Hammond Castle! Start the day with a pickup at your door and a...

7 hours Hotel pickup offered Free Cancellation

4.8 (17)

from
$157

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?