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Top Massachusetts Luxury Tours

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Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of...

90 to 120 minutes Free Cancellation
4.8 (654)
from
$54
Boston City View Bicycle Tour: Historical E-bike/City Bike Tour

Discover Boston’s famous sites and hidden treasures on this 2.5 to 3-hour guided bike tour – a perfect way to explore the city! Start in …More

Boston, USA

Discover Boston’s famous sites and hidden treasures on this 2.5 to 3-hour guided bike tour – a perfect way to explore the city! Start in...

2 hours 30 minutes Free Cancellation
4.9 (636)
from
$78
North End Boston Food Tour: Pizza, Pasta, Pastry, Wine,Apertivo

As a lifelong resident of the North End of Boston this isn’t just about what you eat—it’s about where you are and who you’re with. …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

As a lifelong resident of the North End of Boston this isn’t just about what you eat—it’s about where you are and who you’re with....

2 to 3 hours Free Cancellation
5.0 (589)
from
$98
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

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
The Lucinda Lipol Tour of Provincetown

Formerly the Anne Hutchinson Tour of Provincetown, Lucinda Liphol has taken over the talking points. Her tongue is so sharp she can't close her mouth! …More

Cape Cod, USA

Formerly the Anne Hutchinson Tour of Provincetown, Lucinda Liphol has taken over the talking points. Her tongue is so sharp she can't close her mouth!...

45 to 60 minutes Free Cancellation
4.9 (404)
from
$35
Walk the Historic Freedom Trail with Costumed Guide

Walk the historic Freedom Trail with us and see 11 of 16 sights, the perfect length to keep you absorbed and entertained while learning at …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

Walk the historic Freedom Trail with us and see 11 of 16 sights, the perfect length to keep you absorbed and entertained while learning at...

1 hour 30 minutes Free Cancellation
4.8 (371)
from
$30
Forest Lore Tour

Unlike any walking tour in Salem, the Forest Lore Tour takes you outside the heart of downtown and into one of the few remaining wild …More

Salem, USA
4.9 (325)

Forest Lore Tour

Unlike any walking tour in Salem, the Forest Lore Tour takes you outside the heart of downtown and into one of the few remaining wild...

60 to 90 minutes Free Cancellation
4.9 (325)
from
$43
2-Hour Beacon Hill True Crime Expert Guided Tour

Step into the dark side of Boston’s past on this gripping true-crime walking tour through historic Beacon Hill. Beneath the neighborhood’s elegant brownstones and gaslit …More

Boston, USA

Step into the dark side of Boston’s past on this gripping true-crime walking tour through historic Beacon Hill. Beneath the neighborhood’s elegant brownstones and gaslit...

2 hours Free Cancellation
4.9 (269)
from
$35
Signature Boston Guided Brewery Tour with snack

As we pick you up in downtown Boston in our comfortable brew van, get prepared for the the ultimate all-inclusive Boston craft beer experience!  For …More

Boston, USA

As we pick you up in downtown Boston in our comfortable brew van, get prepared for the the ultimate all-inclusive Boston craft beer experience!  For...

3 hours
4.9 (268)
from
$119
Boston Seafood Lovers Food and History Walking Tour

A true sea food lover never settles for just samples. Enjoy a FULL SIZE Lobster Roll at one of four Sit-Down stops on this unique …More

Boston, USA

A true sea food lover never settles for just samples. Enjoy a FULL SIZE Lobster Roll at one of four Sit-Down stops on this unique...

2 hours 45 minutes Free Cancellation
4.9 (245)
from
$179
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 …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

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 (217)
from
$99
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

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
Boston Harbor Sunset Sail Tour

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. …More

Likely to Sell Out
Likely to Sell Out
Boston, USA

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon....

2 hours Free Cancellation
4.9 (189)
from
$82
North End and Boston Market District Food Tour with Local Guide

Recognized by Yelp as Massachusetts #1 food tour in 2025! Locally owned by Boston native. Specialize in award-winning best eats, culinary education, and history. Part …More

Boston, USA

Recognized by Yelp as Massachusetts #1 food tour in 2025! Locally owned by Boston native. Specialize in award-winning best eats, culinary education, and history. Part...

3 hours 30 minutes Free Cancellation
4.9 (185)
from
$125
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 …More

Boston, USA

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
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

Likely to Sell Out
Likely to Sell Out
Boston, USA

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
Boston Historic Pubs Tour with Drinks and Tastings Included

Raise a pint to the spirits of Samuel Adams, Paul Revere and George Washington as you relive almost 400 years of Tavern History in Boston. …More

Boston, USA

Raise a pint to the spirits of Samuel Adams, Paul Revere and George Washington as you relive almost 400 years of Tavern History in Boston....

3 hours 30 minutes Free Cancellation
4.9 (175)
from
$149
Salem Kids Slightly Spooky Tour

This experience is for kids age 6-14. Meets at 18 Broad St. Salem. All of the guides are certified teachers who hold Master's degrees in …More

Salem, USA

This experience is for kids age 6-14. Meets at 18 Broad St. Salem. All of the guides are certified teachers who hold Master's degrees in...

1 hour Free Cancellation
4.9 (172)
from
$20
2 Hour North End 'Little Italy' Walking Tour

Boston’s North End is the city’s oldest residential neighborhood and one of its most vibrant. Over time it transformed into Boston’s beloved “Little Italy,” thanks …More

Boston, USA

Boston’s North End is the city’s oldest residential neighborhood and one of its most vibrant. Over time it transformed into Boston’s beloved “Little Italy,” thanks...

2 hours Free Cancellation
4.8 (161)
from
$35
Illustrious Schools: Group Tour of MIT And Harvard

The tour starts on the MIT campus, where you will follow your guide to learn about the school's history, famous pranks, inventions, and much more! …More

Likely to Sell Out
Likely to Sell Out
Cambridge, USA

The tour starts on the MIT campus, where you will follow your guide to learn about the school's history, famous pranks, inventions, and much more!...

3 hours 30 minutes Free Cancellation
4.9 (152)
from
$52

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