Top Massachusetts Luxury & Special Occasions

Q: What are the best options for Massachusetts Luxury & Special Occasions?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Massachusetts Luxury & Special Occasions are: America's 250th Anniversary Revolutionary Boston History Tour Santa Brunch Cruise in Boston Harbor Boston to Coastal Maine Private Day Trip Private Walking tour of Boston's Freedom Trail and more! New York City Day Tour from Boston

Q: What are the best kid-friendly options for Massachusetts Luxury & Special Occasions Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Massachusetts Luxury & Special Occasions are: Boston Duck Boat Sightseeing City Tour with Cruise Boston Ghosts and Gravestones Trolley Tour Boston Hop-On Hop-Off Trolley Tour with 11 Stops History and Hauntings of Salem Guided Walking Tour Whale Watching Tour in Gloucester View all kid-friendly Tours →

Q: Which Massachusetts Luxury & Special Occasions have Instant Confirmation?

Massachusetts Luxury & Special Occasions with Instant Confirmation include: Boston Hop-On Hop-Off Trolley Tour with 11 Stops History and Hauntings of Salem Guided Walking Tour Salem Ghost Tour Harvard University Campus Guided Walking Tour City Cruises Boston Historic Sightseeing Harbor Cruise View all Tours with Instant Confirmation →

Q: Which Massachusetts Luxury & Special Occasions have Free Cancellation?

Massachusetts Luxury & Special Occasions with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include: Boston Duck Boat Sightseeing City Tour with Cruise Boston Ghosts and Gravestones Trolley Tour Boston Hop-On Hop-Off Trolley Tour with 11 Stops Whale Watching Tour in Gloucester Salem Ghost Tour View all Tours with Free Cancellation →

Q: I need a ride! Which Massachusetts Luxury & Special Occasions have Hotel Pickup?

No problem. These Massachusetts Luxury & Special Occasions include Hotel Pickup: Boston to Martha's Vineyard Day Trip with Optional Island Tour Private Day Trip to Lexington and Concord from Boston Salem Full Day Private Tour from Boston Cambridge, Lexington, & Concord: Private Revolutionary War Tour 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 →

America's 250th Anniversary Revolutionary Boston History Tour

Celebrate America's 250th anniversary with a vibrant 75-minute guided history tour in Boston. Follow the footsteps of the founding fathers as you walk the forgotten …More

Boston, USA

5.0 (2)

America's 250th Anniversary Revolutionary Boston History Tour

Celebrate America's 250th anniversary with a vibrant 75-minute guided history tour in Boston. Follow the footsteps of the founding fathers as you walk the forgotten...

1 hour 15 minutes Free Cancellation

5.0 (2)

from
$35

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

Boston to Coastal Maine Private Day Trip

Take a break from the city and head north to explore beautiful, coastal Maine. With this private, full-day trip you'll enjoy roundtrip transportation with a private …More

Boston, USA

4.2 (9)

Boston to Coastal Maine Private Day Trip

Take a break from the city and head north to explore beautiful, coastal Maine. With this private, full-day trip you'll enjoy roundtrip transportation with a private...

10 hours Hotel pickup offered Free Cancellation

4.2 (9)

from
$1,200

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

Travel from Boston to New York for a concentrated sightseeing day in Manhattan. The mandatory New York City Fortune Tour covers major financial, commercial, and …More

Boston, USA

4.5 (32)

New York City Day Tour from Boston

Travel from Boston to New York for a concentrated sightseeing day in Manhattan. The mandatory New York City Fortune Tour covers major financial, commercial, and...

15 hours 30 minutes Free Cancellation

4.5 (32)

from
$184

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

Plymouth & South Shore Private Tour from Boston

This full day private tour combines some of the best coastal views in the region with Pilgrim history. First stop focuses on the Presidential history …More

Boston, USA

5.0 (6)

Plymouth & South Shore Private Tour from Boston

This full day private tour combines some of the best coastal views in the region with Pilgrim history. First stop focuses on the Presidential history...

6 hours Hotel pickup offered Free Cancellation

5.0 (6)

from
$995

Boston Food & Cocktail Tour: Discover the South End After Hours

Local Foods, Libations & Lots of Fun! Visit the local eateries Boston's South End residents call home. Walk to 4 different locations, where each visit …More

Boston, USA

5.0 (13)

Boston Food & Cocktail Tour: Discover the South End After Hours

Local Foods, Libations & Lots of Fun! Visit the local eateries Boston's South End residents call home. Walk to 4 different locations, where each visit...

2 hours 30 minutes Free Cancellation

5.0 (13)

from
$135

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

There’s tons of options for things to do in this city, and tons of Tour Guides…while you’re here, come hang out with the most colorful …More

Boston, USA

5.0 (14)

Pizza Beer and Paul Revere Tour

There’s tons of options for things to do in this city, and tons of Tour Guides…while you’re here, come hang out with the most colorful...

2 hours Free Cancellation

5.0 (14)

from
$75

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

Explore Boston's rich sports history on foot! Dynasty beginnings to banner nights—experience the legacies that make this town shimmer! Come discover why Boston gets its …More

Boston, USA

5.0 (4)

Title Town Sports Walking Tour

Explore Boston's rich sports history on foot! Dynasty beginnings to banner nights—experience the legacies that make this town shimmer! Come discover why Boston gets its...

2 hours Free Cancellation

5.0 (4)

from
$35

Tour to Plymouth including Plimoth Patuxet Museum and Mayflower

Plymouth Colony comes to life in our recreation of early Plymouth, complete with timber-framed houses furnished with reproductions of the types of objects that the …More

Boston, USA

5.0 (6)

Tour to Plymouth including Plimoth Patuxet Museum and Mayflower

Plymouth Colony comes to life in our recreation of early Plymouth, complete with timber-framed houses furnished with reproductions of the types of objects that the...

8 hours Free Cancellation

5.0 (6)

from
$279

Guided Tour of Crane Estate All-Inclusive Day Trip from Boston

Step into the grandeur of New England’s past with a visit to Castle Hill on the Crane Estate, a breathtaking National Historic Landmark overlooking the …More

5.0 (3)

Guided Tour of Crane Estate All-Inclusive Day Trip from Boston

Step into the grandeur of New England’s past with a visit to Castle Hill on the Crane Estate, a breathtaking National Historic Landmark overlooking the...

6 hours Free Cancellation

5.0 (3)

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 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

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