Top Massachusetts Tours & Sightseeing

Q: I need a ride! Which Massachusetts Tours & Sightseeing have Hotel Pickup?

No problem. These Massachusetts Tours & Sightseeing 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 Portland: Lighthouse, Old Port and Park 1-Day Tour from Boston 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 →

From Boston: Holiday Lights Trip to New England Botanic Gardens

Experience the Magic of USA TODAY's #1 Best Botanical Garden Holiday Light Display! ✨ Step into a world of holiday magic at New England Botanic …More

4.8 (4)

From Boston: Holiday Lights Trip to New England Botanic Gardens

Experience the Magic of USA TODAY's #1 Best Botanical Garden Holiday Light Display! ✨ Step into a world of holiday magic at New England Botanic...

4 hours

4.8 (4)

from
$90

Boston's Food and History: North End, Freedom Trail, Beacon Hill

Uncover Boston’s best-kept secrets on a walking tour that blends history, culture, and flavor. Wander through the iconic North End, tasting fresh bread, pastries, pizza, …More

Boston, USA

4.9 (1,930)

Boston's Food and History: North End, Freedom Trail, Beacon Hill

Uncover Boston’s best-kept secrets on a walking tour that blends history, culture, and flavor. Wander through the iconic North End, tasting fresh bread, pastries, pizza,...

5 hours Free Cancellation

4.9 (1,930)

from
$91

Boston's Revolutionary and Drunken Past with Beer Included

When visiting Boston, the Freedom Trail is a must-do activity, but why not see historic sites while drinking beer? Join Ye Olde Tavern Tours to …More

Boston, USA

5.0 (216)

Boston's Revolutionary and Drunken Past with Beer Included

When visiting Boston, the Freedom Trail is a must-do activity, but why not see historic sites while drinking beer? Join Ye Olde Tavern Tours to...

2 hours

5.0 (216)

from
$91

Truro Cape Cod Lighthouse and Highland House Museum Tour

Step into Cape history with a visit to Highland Lighthouse—Cape Cod’s oldest and tallest lighthouse, proudly standing watch over the Atlantic since 1797. Once a …More

Cape Cod, USA

4.7 (21)

Truro Cape Cod Lighthouse and Highland House Museum Tour

Step into Cape history with a visit to Highland Lighthouse—Cape Cod’s oldest and tallest lighthouse, proudly standing watch over the Atlantic since 1797. Once a...

2 hours Free Cancellation

4.7 (21)

from
$95

From Boston Day Trip to Plimoth Patuxet Museums and Mayflower II

Explore the rich history of Plymouth, Massachusetts, on this immersive day trip. Starting with a scenic ride on the MBTA Commuter Rail, visit the renowned …More

Plymouth, USA

5.0 (3)

From Boston Day Trip to Plimoth Patuxet Museums and Mayflower II

Explore the rich history of Plymouth, Massachusetts, on this immersive day trip. Starting with a scenic ride on the MBTA Commuter Rail, visit the renowned...

8 hours Free Cancellation

5.0 (3)

from
$98

Boston’s Politically Incorrect North End Food Tour

As the title suggests, Boston’s “Politically Incorrect “ Food Tour isn’t going to be your typical food tour. With his no BS style, your tour …More

Boston, USA

4.8 (849)

Boston’s Politically Incorrect North End Food Tour

As the title suggests, Boston’s “Politically Incorrect “ Food Tour isn’t going to be your typical food tour. With his no BS style, your tour...

3 hours Free Cancellation

4.8 (849)

from
$99

Get the true Boston experience with your 2-hour Segway tour! Starting with the same route as your 1-hour tour before gliding your way through the …More

Boston, USA

5.0 (218)

2 Hour Boston Segway Tour

Get the true Boston experience with your 2-hour Segway tour! Starting with the same route as your 1-hour tour before gliding your way through the...

2 hours 30 minutes

5.0 (218)

from
$99

Boston's Emerald Necklace Guided Bicycle Tour: E-Bikes/City Bikes

The Emerald Necklace bike tour is an amazing way to see Boston’s most famous green spaces in a ‘green’ way - you may forget you …More

Boston, USA

4.7 (15)

Boston's Emerald Necklace Guided Bicycle Tour: E-Bikes/City Bikes

The Emerald Necklace bike tour is an amazing way to see Boston’s most famous green spaces in a ‘green’ way - you may forget you...

4 hours

4.7 (15)

from
$99

Boston North End Food and History Tour Stories Behind the Bites

Discover Boston's oldest neighborhood on a food tour that's equal parts delicious and "mostly" accurate. Join a local guide as you wander the cobblestone streets …More

Boston, USA

5.0 (8)

Boston North End Food and History Tour Stories Behind the Bites

Discover Boston's oldest neighborhood on a food tour that's equal parts delicious and "mostly" accurate. Join a local guide as you wander the cobblestone streets...

3 hours Free Cancellation

5.0 (8)

from
$99

Boston North End Food Tour with Wine and Limoncello Tasting

We never leave the neighborhood – we only walk three blocks. But we metaphorically travel the whole peninsula of Italy, tasting the regional foods so …More

Boston, USA

5.0 (540)

Boston North End Food Tour with Wine and Limoncello Tasting

We never leave the neighborhood – we only walk three blocks. But we metaphorically travel the whole peninsula of Italy, tasting the regional foods so...

3 hours Free Cancellation

5.0 (540)

from
$100

15 Minute Portraits - Historic Downtown Boston

Take Home your Boston Memories You will be professionally photographed by a local, in a picturesque part of historic Boston. What better way to preserve …More

Boston, USA

5.0 (1)

15 Minute Portraits - Historic Downtown Boston

Take Home your Boston Memories You will be professionally photographed by a local, in a picturesque part of historic Boston. What better way to preserve...

15 minutes Free Cancellation

5.0 (1)

from
$100

Boston: Martha's Vineyard ICONIC Small Group Day Escape w/Ferry

Leave Boston behind and set out on a full-day journey to Martha's Vineyard, one of New England's most beloved islands. This experience blends a scenic …More

Boston, USA

4.6 (53)

Boston: Martha's Vineyard ICONIC Small Group Day Escape w/Ferry

Leave Boston behind and set out on a full-day journey to Martha's Vineyard, one of New England's most beloved islands. This experience blends a scenic...

12 hours Free Cancellation

4.6 (53)

from
$100

Freedom Trail and North End History and Culinary Delights Tour

This small-group tour stands out by offering an intimate, authentic experience, allowing guests to connect more deeply with Boston’s local stories. With a focus on …More

Boston, USA

5.0 (1)

Freedom Trail and North End History and Culinary Delights Tour

This small-group tour stands out by offering an intimate, authentic experience, allowing guests to connect more deeply with Boston’s local stories. With a focus on...

4 hours Free Cancellation

5.0 (1)

from
$102

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

The Signature Boston Brew Tour is the perfect introduction to Boston's impressive and world-renowned craft beverage scene. On this compact, three and a half hour …More

Boston, USA

4.9 (184)

Boston Signature Guided Brewery Tour

The Signature Boston Brew Tour is the perfect introduction to Boston's impressive and world-renowned craft beverage scene. On this compact, three and a half hour...

3 hours 30 minutes Free Cancellation

4.9 (184)

from
$105

Enjoy a delicious 2-hour brunch cruise and take in historic sights along the water including Castle and Deer Island, Spectacle Island, Long Island, Lovells Island, …More

Boston, USA

4.6 (163)

Boston Harbor Brunch Cruise

Enjoy a delicious 2-hour brunch cruise and take in historic sights along the water including Castle and Deer Island, Spectacle Island, Long Island, Lovells Island,...

2 hours Free Cancellation

4.6 (163)

from
$106

Enjoy a delicious gourmet brunch buffet on this 2-hour scenic holiday cruise of the Boston Harbor and get into the holiday spirit. Enjoy a cruise …More

Boston, USA

4.8 (9)

Santa Brunch Cruise in Boston Harbor

Enjoy a delicious gourmet brunch buffet on this 2-hour scenic holiday cruise of the Boston Harbor and get into the holiday spirit. Enjoy a cruise...

2 hours Free Cancellation

4.8 (9)

from
$106

Portland: Lighthouse, Old Port and Park 1-Day Tour from Boston

Escape Boston for a full day along the southern Maine coast, blending scenic seaside walks, historic harbor towns, and iconic lighthouse views. Begin at Marginal …More

Boston, USA

4.7 (25)

Portland: Lighthouse, Old Port and Park 1-Day Tour from Boston

Escape Boston for a full day along the southern Maine coast, blending scenic seaside walks, historic harbor towns, and iconic lighthouse views. Begin at Marginal...

9 to 11 hours Hotel pickup offered Free Cancellation

4.7 (25)

from
$110

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

New York Bus Day Tour-One World Trade&Liberty Cruise From NY/BOS

Travel with a knowledgeable sightseeing coach and our professional trained tour escort. Visit one of the world’s greatest financial centers at Wall Streets! Take a …More

Brooklyn, USA

4.5 (2)

New York Bus Day Tour-One World Trade&Liberty Cruise From NY/BOS

Travel with a knowledgeable sightseeing coach and our professional trained tour escort. Visit one of the world’s greatest financial centers at Wall Streets! Take a...

8 hours

4.5 (2)

from
$119

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Massachusetts Tours & Sightseeing?

What are the best kid-friendly options for Massachusetts Tours & Sightseeing Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Massachusetts Tours & Sightseeing are:

View all kid-friendly Tours →

Which Massachusetts Tours & Sightseeing have Instant Confirmation?

Massachusetts Tours & Sightseeing with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Massachusetts Tours & Sightseeing have Free Cancellation?

Massachusetts Tours & Sightseeing 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 Tours & Sightseeing have Hotel Pickup?

Got any more Massachusetts trip ideas?

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