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: Private Walking Tour with a Local Guide in Boston Private Half-Day Driving Tour of Boston and Cambridge Private Tour of Boston for Families & Kids Private Open-Air Pedicab Tour in Provincetown Private Open- Air Pedicab Tour in Provincetown 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 →

Private Half-Day Driving Tour of Boston and Cambridge

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. This is a half-day driving tour that takes you …More

Boston, USA

5.0 (7)

Private Half-Day Driving Tour of Boston and Cambridge

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. This is a half-day driving tour that takes you...

4 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$88

Private Tour of Boston for Families & Kids

Spend a great day in Boston learning about history and exploring all the top attractions! The tour is designed to be fun for the whole …More

Boston, USA

5.0 (2)

Private Tour of Boston for Families & Kids

Spend a great day in Boston learning about history and exploring all the top attractions! The tour is designed to be fun for the whole...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$104

Ready to taste Ptown? Lace up for a 2-hour trek through history and coastal rebel lore. You’ll track the footsteps of Anthony Bourdain and dive …More

Cape Cod, USA

5.0 (20)

Local Legends and Lobster Roll Tour

Ready to taste Ptown? Lace up for a 2-hour trek through history and coastal rebel lore. You’ll track the footsteps of Anthony Bourdain and dive...

2 hours Free Cancellation

5.0 (20)

from
$105

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

Chatham Bites and Sights Walking Guided Food Tasting Tour

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by …More

Cape Cod, USA

5.0 (91)

Chatham Bites and Sights Walking Guided Food Tasting Tour

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by...

3 hours Free Cancellation

5.0 (91)

from
$119

Discover Provincetown from a new perspective with our Private Open-Air Pedicab Tours. Relax in comfort as our knowledgeable guides lead you through the charming streets …More

Cape Cod, USA

3.5 (2)

Private Open- Air Pedicab Tour in Provincetown

Discover Provincetown from a new perspective with our Private Open-Air Pedicab Tours. Relax in comfort as our knowledgeable guides lead you through the charming streets...

60 to 90 minutes Hotel pickup offered Free Cancellation

3.5 (2)

from
$126

Private Tour of Lexington, Concord, and Boston

Visit the real locations where the American Revolution began. Stand on Lexington Battle Green and listen to stories about the very first days of the …More

Boston, USA

4.9 (8)

Private Tour of Lexington, Concord, and Boston

Visit the real locations where the American Revolution began. Stand on Lexington Battle Green and listen to stories about the very first days of the...

7 hours Hotel pickup offered Free Cancellation

4.9 (8)

from
$126

Boston Massachusetts Private Photography Tour

We are soulful photographers. Our objective is to create absolutely stunning photographs for you that you will cherish and proudly share with your friends and …More

Boston, USA

5.0 (3)

Boston Massachusetts Private Photography Tour

We are soulful photographers. Our objective is to create absolutely stunning photographs for you that you will cherish and proudly share with your friends and...

1 hour Free Cancellation

5.0 (3)

from
$130

A full-day tour of Boston's history, culture, and food! Visit the historic North End and walk in the steps of Paul Revere. Stroll amongst the …More

Boston, USA

4.9 (37)

Highlights of Boston Private Tour

A full-day tour of Boston's history, culture, and food! Visit the historic North End and walk in the steps of Paul Revere. Stroll amongst the...

5 hours 30 minutes Hotel pickup offered Free Cancellation

4.9 (37)

from
$135

Yelp's 2025 pick for Massachusetts #1 food tour! Create food memories with one of Boston's original food tours. Our North End Neighborhood Tour offers a …More

Boston, USA

5.0 (33)

Private North End Neighborhood Tour

Yelp's 2025 pick for Massachusetts #1 food tour! Create food memories with one of Boston's original food tours. Our North End Neighborhood Tour offers a...

3 hours 30 minutes Free Cancellation

5.0 (33)

from
$135

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

The Best of Boston: Private Half-Day Highlights Driving Tour

See the best of Boston from one end of the city to the other on this private, half-day driving highlights tour. If you are arriving …More

Boston, USA

5.0 (3)

The Best of Boston: Private Half-Day Highlights Driving Tour

See the best of Boston from one end of the city to the other on this private, half-day driving highlights tour. If you are arriving...

3 hours Hotel pickup offered

5.0 (3)

from
$140

Whirlwind full-day tour of Boston and Salem! Drive to Salem to learn about the witch hunt hysteria of the late 17th century. Walk through historic …More

Boston, USA

5.0 (31)

Private Day Tour of Salem and Boston

Whirlwind full-day tour of Boston and Salem! Drive to Salem to learn about the witch hunt hysteria of the late 17th century. Walk through historic...

7 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (31)

from
$143

Private City Tour of Boston and Cambridge

This private full-day tour will take you through every highlight Boston and Cambridge! The tour will include sights such as the Old North Church, Paul …More

Boston, USA

5.0 (45)

Private City Tour of Boston and Cambridge

This private full-day tour will take you through every highlight Boston and Cambridge! The tour will include sights such as the Old North Church, Paul...

7 hours Hotel pickup offered Free Cancellation

5.0 (45)

from
$149

Private Day Trip to Lexington and Concord from Boston

Visit the real locations where the American Revolution began, while listening to hilarious yet little-known stories about our ancestors. Stand on Lexington Battle Green and …More

Boston, USA

5.0 (36)

Private Day Trip to Lexington and Concord from Boston

Visit the real locations where the American Revolution began, while listening to hilarious yet little-known stories about our ancestors. Stand on Lexington Battle Green and...

6 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (36)

from
$149

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past …More

Boston, USA

5.0 (10)

Salem Full Day Private Tour from Boston

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past...

8 hours Hotel pickup offered Free Cancellation

5.0 (10)

from
$155

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

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

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

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

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?

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?

Got any more Massachusetts trip ideas?

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