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Top 10 Best Massachusetts Private Sightseeing Tours

Found 168 Private Sightseeing Tours activities in Massachusetts. Sort by Popularity.
 

Highlights of Boston Private Tour

(4.9 of 24 reviews)

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 brownstones on streets lit by gas lamps in Beacon Hill, Boston's most prestigious neighb... More

Free Cancellation
Private Tour
Start From $390.00
 
Highlights of Boston Private Tour

Highlights of Boston Private Tour

  • Massachusetts
  • Superb24 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $390.00
 
 

Private Day Trip to Lexington and Concord from Boston

(5 of 16 reviews)

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 listen to stories about the very first days of the war an... More

Free Cancellation
Private Tour
Start From $493.00
 
Private Day Trip to Lexington and Concord from Boston

Private Day Trip to Lexington and Concord from Boston

  • Massachusetts
  • Superb16 reviews5

Visit the real locations where the American Revolution began, while listening to hilarious yet littl....

    Free Cancellation
    Private Tour
    Start From $493.00
 
 

Chatham Bites and Sights Walking Guided Food Tasting Tour

(5 of 25 reviews)

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 a local expert, this 3-hour walking tour features multiple tasting stops with hand-... More

Free Cancellation
Private Tour
Start From $98.00
 
Chatham Bites and Sights Walking Guided Food Tasting Tour

Chatham Bites and Sights Walking Guided Food Tasting Tour

  • Massachusetts
  • Superb25 reviews5

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chathamâ€....

    Free Cancellation
    Private Tour
    Start From $98.00
 
 

Boston Private Driving City Tour, groups of 1-4

(5 of 118 reviews)

This tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On this tour we'll take you into all the city neighborhoods and along the sites of the Freedom Trail. We'll s... More

Free Cancellation
Private Tour
Start From $525.00
 
Boston Private Driving City Tour, groups of 1-4

Boston Private Driving City Tour, groups of 1-4

  • Massachusetts
  • Superb118 reviews5

This tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, bu....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

Private City Tour of Boston, Lexington, and Concord

(4.8 of 8 reviews)

See all Boston's most important sights in a six hours, private, guided city tour, in a comfortable vehicle. If you value, time, privacy, comfort and would like to have a good overview of the city of Boston, Lexington and Concord a... More

Free Cancellation
Private Tour
Start From $799.85
 
Private City Tour of Boston, Lexington, and Concord Likely to Sell Out

Private City Tour of Boston, Lexington, and Concord

  • Massachusetts
  • Superb8 reviews4.8

See all Boston's most important sights in a six hours, private, guided city tour, in a comfortable v....

    Free Cancellation
    Private Tour
    Start From $799.85
 
 

Boston North-End Private Walking Food Tour With Secret Food Tours

(4.9 of 155 reviews)

On our Secret Food Tour: Boston, you'll savor the freshest seafood and the famous Italian dishes that have been a staple in the North End for the past 100 years. As you explore the vibrant culinary scene, you will learn about the ... More

Free Cancellation
Private Tour
Start From $395.00
 
Boston North-End Private Walking Food Tour With Secret Food Tours Likely to Sell Out

Boston North-End Private Walking Food Tour With Secret Food Tours

  • Massachusetts
  • Superb155 reviews4.9

On our Secret Food Tour: Boston, you'll savor the freshest seafood and the famous Italian dishes tha....

    Free Cancellation
    Private Tour
    Start From $395.00
 
 

Boston Private City Tour

(4.6 of 65 reviews)

See all Boston's most important sights in a four hour, private, guided city tour, in a comfortable luxury vehicle. If you value, time, privacy, comfort and would like to have a good overview of the city of Boston at your own conve... More

Free Cancellation
Private Tour
Start From $616.44
 
Boston Private City Tour Likely to Sell Out

Boston Private City Tour

  • Massachusetts
  • Superb65 reviews4.6

See all Boston's most important sights in a four hour, private, guided city tour, in a comfortable l....

    Free Cancellation
    Private Tour
    Start From $616.44
 
 

Boston Sightseeing Tour - a fully-narrated driving tour

(4.9 of 54 reviews)

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 House, the USS Constitution, the Bunker Hill Battle Monument, Copley Square and Fenway Park.... More

Free Cancellation
Private Tour
Start From $495.00
 
Boston Sightseeing Tour - a fully-narrated driving tour Likely to Sell Out

Boston Sightseeing Tour - a fully-narrated driving tour

  • Massachusetts
  • Superb54 reviews4.9

This tour will begin at your home, hotel or cruise ship and take you past the most interesting place....

    Free Cancellation
    Private Tour
    Start From $495.00
 
 

Marthas Vineyard Luxury Tour (2hrs)

(5 of 25 reviews)

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 this narrated tour as we drive along the scenic coast, stop for ... More

Free Cancellation
Private Tour
Start From $525.00
 
Marthas Vineyard Luxury Tour (2hrs) Likely to Sell Out

Marthas Vineyard Luxury Tour (2hrs)

  • Massachusetts
  • Superb25 reviews5

Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people....

    Free Cancellation
    Private Tour
    Start From $525.00
 
 

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

(4.9 of 17 reviews)

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 take you past the most interesting places in Boston including the Paul Revere House, the US... More

Free Cancellation
Private Tour
Start From $495.00
 
3-Hour Private Likely to Sell Out

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

  • Massachusetts
  • Superb17 reviews4.9

This tour will begin at your home, hotel or cruise ship and will be conducted in a comfortable heate....

    Free Cancellation
    Private Tour
    Start From $495.00
 
 

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

(5 of 1 review)

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 in Boston with no idea where to start or how to orient yourself, then this is the perfect tour â... More

Free Cancellation
Private Tour
Start From $420.00
 
The Best of Boston: Private Half-Day Highlights Driving Tour Likely to Sell Out

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

  • Massachusetts
  • Superb1 review5

See the best of Boston from one end of the city to the other on this private, half-day driving highl....

    Free Cancellation
    Private Tour
    Start From $420.00
 
 

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

(4.9 of 82 reviews)

-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 this narrated tour as we drive along the scenic coast, stop fo... More

Free Cancellation
Private Tour
Start From $650.00
 
Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs) Likely to Sell Out

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

  • Massachusetts
  • Superb82 reviews4.9

-Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of peopl....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

Salem Private Half Day Tour from Boston, groups 5-6

(5 of 1 review)

If you've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day tour has a Downtown Boston pick up. It's a 45 minute drive to Salem, when we'll tell some of the quirky stories abou... More

Free Cancellation
Private Tour
Start From $795.00
 
Salem Private Half Day Tour from Boston, groups 5-6 Likely to Sell Out

Salem Private Half Day Tour from Boston, groups 5-6

  • Massachusetts
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $795.00
 
 

Private Day Trip to Salem and Hammond Castle from Boston

(4.7 of 11 reviews)

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 comfortable ride to Hammond Castle, located on the ocean cliffs of Gloucester. Take a guided to... More

Free Cancellation
Private Tour
Start From $495.00
 
Private Day Trip to Salem and Hammond Castle from Boston Likely to Sell Out

Private Day Trip to Salem and Hammond Castle from Boston

  • Massachusetts
  • Superb11 reviews4.7

Enjoy a unique day trip to Boston's northern shore, combining Salem and Hammond Castle! Start the da....

    Free Cancellation
    Private Tour
    Start From $495.00
 
 

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

(4.5 of 235 reviews)

Discover Boston's Revolutionary history on this Classic Freedom Trail Walking Tour including Historic Downtown Boston, the North End and Charlestown. -Go anytime, at your own pace and your schedule. -Navigated by the WalknTours ... More

Free Cancellation
Private Tour
Start From $7.75
 
Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour Likely to Sell Out

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Au....

  • Massachusetts
  • Exellent235 reviews4.5

Discover Boston's Revolutionary history on this Classic Freedom Trail Walking Tour including Histori....

    Free Cancellation
    Private Tour
    Start From $7.75
 
 

Salem Private Half Day Tour from Boston, for groups 1-4

(5 of 13 reviews)

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 consists of: - Downtown Boston pick up, ~45 minute drive to Salem - Stories of what happened b... More

Free Cancellation
Private Tour
Start From $675.00
 
Salem Private Half Day Tour from Boston, for groups 1-4 Likely to Sell Out

Salem Private Half Day Tour from Boston, for groups 1-4

  • Massachusetts
  • Superb13 reviews5

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

    Free Cancellation
    Private Tour
    Start From $675.00
 
 

Private North End Neighborhood Tour

(5 of 20 reviews)

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 view of Boston's Little Italy from the perspective of our founder, a native ... More

Free Cancellation
Private Tour
Start From $135.00
 
Private North End Neighborhood Tour Likely to Sell Out

Private North End Neighborhood Tour

  • Massachusetts
  • Superb20 reviews5

Yelp's 2025 pick for Massachusetts #1 food tour! Create food memories with one of Boston's original ....

    Free Cancellation
    Private Tour
    Start From $135.00
 
 

Private Half-Day Driving Tour of Boston and Cambridge

(5 of 1 review)

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 through every highlight of Boston and Cambridge. The drive will include sights such as... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Half-Day Driving Tour of Boston and Cambridge Likely to Sell Out

Private Half-Day Driving Tour of Boston and Cambridge

  • Massachusetts
  • Superb1 review5

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. Thi....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Ultimate Historic Salem and Witch Trials Self-Guided Walking Tour

(4.3 of 65 reviews)

Uncover the truth behind the infamous Salem Witch Trials with this self-guided walking tour of Salem, Massachusetts! This quaint and picturesque town hides a seriously dark history, and you’ll dive deep into that past as you exp... More

Special Offer
Free Cancellation
Private Tour
Start From $15.29
(Saving 10% ) $16.99
 
-10% Ultimate Historic Salem and Witch Trials Self-Guided Walking Tour Likely to Sell Out

Ultimate Historic Salem and Witch Trials Self-Guided Walking Tour

  • Massachusetts
  • Exellent65 reviews4.3

Uncover the truth behind the infamous Salem Witch Trials with this self-guided walking tour of Salem....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $15.29
    (Saving 10% ) $16.99
 
 

Boston Food and History Private Tour

(5 of 9 reviews)

Start the day in Little Italy, with traditional cannoli and espresso at the oldest Italian café in Boston. Proceed through the historic "Little Italy" neighborhood to learn about Boston's history! Listen to stories about the neig... More

Free Cancellation
Private Tour
Start From $528.50
 
Boston Food and History Private Tour Likely to Sell Out

Boston Food and History Private Tour

  • Massachusetts
  • Superb9 reviews5

Start the day in Little Italy, with traditional cannoli and espresso at the oldest Italian café in ....

    Free Cancellation
    Private Tour
    Start From $528.50
 
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