Top Day Trips from Massachusetts (Updated November 2026)

Massachusetts, USA
Self Guided Driving Audio Tour Cape Cod

Download GuideAlong's Cape Cod audio tour to discover what “summer” really means. Drive the iconic “bent arm” between Barnstable and Provincetown, with side trips to …More

Download GuideAlong's Cape Cod audio tour to discover what “summer” really means. Drive the iconic “bent arm” between Barnstable and Provincetown, with side trips to...

4 to 5 hours Free Cancellation
4.3 (3)
from
$17
Martha's Vineyard at Your Pace: Iconic Cottages & Lighthouses

Welcome to Martha's Vineyard, the storied island off Cape Cod that has captivated visitors for generations with its windswept beaches and fiercely independent spirit. This …More

Welcome to Martha's Vineyard, the storied island off Cape Cod that has captivated visitors for generations with its windswept beaches and fiercely independent spirit. This...

8 hours Free Cancellation
5.0 (1)
from
$5
Boston: Harvard, MIT, Quincy Market Small-Group Full-Day Tour

Discover Boston’s most iconic sights in one perfectly planned day. Walk through the world-famous campuses of Harvard and MIT, where history, innovation, and genius collide. …More

Discover Boston’s most iconic sights in one perfectly planned day. Walk through the world-famous campuses of Harvard and MIT, where history, innovation, and genius collide....

7 to 8 hours Free Cancellation
3.0 (4)
from
$129
Nantucket Coast-to-Coast Self-Guided Audio Driving or Biking Tour

Explore Nantucket from coast to coast on a self-guided audio tour designed for driving or biking. Follow the route from historic Nantucket Town to Madaket, …More

Explore Nantucket from coast to coast on a self-guided audio tour designed for driving or biking. Follow the route from historic Nantucket Town to Madaket,...

3 to 6 hours Free Cancellation
3.0 (4)
from
$13
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

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
Private tour to northern Massachusetts coast from Boston - Hotel pick up

Enjoy this private full day tour with your own private driver and official tour guide and explore the vibrant coast of northern Massachusets. Get ready …More

Enjoy this private full day tour with your own private driver and official tour guide and explore the vibrant coast of northern Massachusets. Get ready...

8 hours Hotel pickup offered Free Cancellation
from
$315
Private Plymouth Day Trip from Boston with Historic Stops

Enjoy a private day trip from Boston to Plymouth with convenient door-to-door transportation and time to explore at your own pace. Depart at approximately 9:00 …More

Enjoy a private day trip from Boston to Plymouth with convenient door-to-door transportation and time to explore at your own pace. Depart at approximately 9:00...

8 hours Hotel pickup offered Free Cancellation
from
$1,090
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