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 1.5-Hour Freedom Trail Walking Tour with Costumed Guide

A 90-minute walking tour of the Freedom Trail that covers the first 11 historic sites. It starts in Boston Common at the Visitor Information Center …More

Boston, USA

4.8 (44)

Private 1.5-Hour Freedom Trail Walking Tour with Costumed Guide

A 90-minute walking tour of the Freedom Trail that covers the first 11 historic sites. It starts in Boston Common at the Visitor Information Center...

90 to 240 minutes Free Cancellation

4.8 (44)

from
$450

Private Boston Freedom Trail Walking Tour

Hire a private tour guide for your 90-minute walking tour of the Freedom Trail. Take your time, and ask any questions you want! We cover the …More

Boston, USA

4.9 (21)

Private Boston Freedom Trail Walking Tour

Hire a private tour guide for your 90-minute walking tour of the Freedom Trail. Take your time, and ask any questions you want! We cover the...

1 hour 30 minutes Free Cancellation

4.9 (21)

from
$450

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

3-Hour Private "Cold Weather- Warm Van" Driving Tour of Boston

This tour will begin at your home, hotel or cruise ship and will be conducted in a comfortable heated minivan, no matter the weather. I'll …More

Boston, USA

4.8 (24)

3-Hour Private "Cold Weather- Warm Van" Driving Tour of Boston

This tour will begin at your home, hotel or cruise ship and will be conducted in a comfortable heated minivan, no matter the weather. I'll...

3 hours Hotel pickup offered Free Cancellation

4.8 (24)

from
$495

Best Boston Private Tour, I know the secrets others don't!

I know the secrets that no one else knows. You will go on a small private tour where you will learn the amazing origins of …More

Boston, USA

4.9 (13)

Best Boston Private Tour, I know the secrets others don't!

I know the secrets that no one else knows. You will go on a small private tour where you will learn the amazing origins of...

6 to 8 hours Hotel pickup offered Free Cancellation

4.9 (13)

from
$499

Boston Private Sightseeing Tour with Daily Chauffeur

With an experienced driver, you can charter a private car for 10 hours to visit the highlights of Boston. If you are not satisfied with …More

Boston, USA

3.0 (1)

Boston Private Sightseeing Tour with Daily Chauffeur

With an experienced driver, you can charter a private car for 10 hours to visit the highlights of Boston. If you are not satisfied with...

10 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$518

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

Boston Sightseeing Tour - a fully-narrated driving tour

This tour will begin at your home, hotel or cruise ship and take you past the most interesting places in Boston including the Paul Revere …More

Boston, USA

4.9 (63)

Boston Sightseeing Tour - a fully-narrated driving tour

This tour will begin at your home, hotel or cruise ship and take you past the most interesting places in Boston including the Paul Revere...

3 hours Hotel pickup offered Free Cancellation

4.9 (63)

from
$549

Experience Martha's Vineyard #1 Private Tours for up to 6 people

This private tour for up to 6ppl will introduce the history of our 6 unique towns! Oak Bluffs, a Victorian seaside, built around the Methodist …More

Martha's Vineyard, USA

4.9 (128)

Experience Martha's Vineyard #1 Private Tours for up to 6 people

This private tour for up to 6ppl will introduce the history of our 6 unique towns! Oak Bluffs, a Victorian seaside, built around the Methodist...

3 hours Hotel pickup offered Free Cancellation

4.9 (128)

from
$550

This private car tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On …More

Boston, USA

5.0 (148)

Boston Private 3-Hour Tour by Car

This private car tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On...

3 hours Hotel pickup offered Free Cancellation

5.0 (148)

from
$550

Lexington and Concord 3 hour private car tour from Boston

This half day private car tour is a perfect way to visit the Revolutionary War towns of Lexington and Concord and see the site where …More

Boston, USA

5.0 (41)

Lexington and Concord 3 hour private car tour from Boston

This half day private car tour is a perfect way to visit the Revolutionary War towns of Lexington and Concord and see the site where...

3 hours Hotel pickup offered Free Cancellation

5.0 (41)

from
$550

Private 4-Hour Driving & Walking City Tour

Private tours are priced per GROUP, not per person. This amazing tour is for those who want more than a driving tour but not a …More

Boston, USA

5.0 (37)

Private 4-Hour Driving & Walking City Tour

Private tours are priced per GROUP, not per person. This amazing tour is for those who want more than a driving tour but not a...

4 hours Hotel pickup offered

5.0 (37)

from
$550

Why Choose Boston Pro's Private Historic Tour? Luxury Experience: Our luxury SUV ensures a comfortable and stylish exploration of Boston's best attractions, including a scenic …More

Cambridge, USA

3.0 (1)

Boston City Private Tour

Why Choose Boston Pro's Private Historic Tour? Luxury Experience: Our luxury SUV ensures a comfortable and stylish exploration of Boston's best attractions, including a scenic...

2 to 3 hours Hotel pickup offered Free Cancellation

3.0 (1)

from
$578

Private Customized Walking Tour of Boston

Discover Boston the way you want to on this 2 to 2.5-hour private walking tour. Customize your itinerary with your guide to ensure you see …More

Boston, USA

4.9 (11)

Private Customized Walking Tour of Boston

Discover Boston the way you want to on this 2 to 2.5-hour private walking tour. Customize your itinerary with your guide to ensure you see...

2 to 2.5 hours Hotel pickup offered Free Cancellation

4.9 (11)

from
$595

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

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, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)

-Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. -Relax and enjoy …More

Martha's Vineyard, USA

4.9 (91)

Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)

-Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. -Relax and enjoy...

3 hours Free Cancellation

4.9 (91)

from
$650

Private Revolutionary Heritage Tour from Boston by Car

This private historical tour explores landscapes where American independence began. You travel from Boston into regions shaped by early revolutionary action. In Boston, streets reveal …More

Boston, USA

Private Revolutionary Heritage Tour from Boston by Car

This private historical tour explores landscapes where American independence began. You travel from Boston into regions shaped by early revolutionary action. In Boston, streets reveal...

6 hours Hotel pickup offered

from
$689

If you've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day Boston to Salem tour …More

Boston, USA

5.0 (16)

Salem half day private tour from Boston

If you've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day Boston to Salem tour...

4 hours Hotel pickup offered Free Cancellation

5.0 (16)

from
$695

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

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?

Got any more Massachusetts trip ideas?

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