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Top Massachusetts Outdoor Activities

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Massachusetts Tours

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Kayak The Creek Nature Tour

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff …More

Likely to Sell Out
Likely to Sell Out
Cape Cod, USA
4.9 (54)

Kayak The Creek Nature Tour

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff...

2 hours • Free Cancellation
4.9 (54)
from
$80
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Recommended: Purchase one tour per car, not per person. Everyone listens together! Discover the natural beauty of New England’s most picturesque coastline with this narrated …More

Gloucester, USA
4.2 (108)

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Recommended: Purchase one tour per car, not per person. Everyone listens together! Discover the natural beauty of New England’s most picturesque coastline with this narrated...

2 to 3 hours • Free Cancellation
4.2 (108)
from
$17
Boston to New Hampshire Fall Foliage White Mountains Day Trip

Enjoy a spectacular day in the White Mountains of New Hampshire viewing the magnificent fall foliage. Your day will begin with front door hotel pick …More

Cambridge, USA
4.9 (248)

Boston to New Hampshire Fall Foliage White Mountains Day Trip

Enjoy a spectacular day in the White Mountains of New Hampshire viewing the magnificent fall foliage. Your day will begin with front door hotel pick...

12 hours • Hotel pickup offered • Free Cancellation
4.9 (248)
from
$150
Cape Cod Explorer Tour

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff …More

Likely to Sell Out
Likely to Sell Out
Cape Cod, USA
5.0 (19)

Cape Cod Explorer Tour

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff...

2 hours • Free Cancellation
5.0 (19)
from
$80
Boston Pass: 40+ Things To Do - Includes Franklin Park Zoo

Go City's All-Inclusive Pass is the best Boston pass if you're looking for an easy-to-use, flexible way to explore the city whilst also saving money. …More

Boston, USA
4.2 (320)

Boston Pass: 40+ Things To Do - Includes Franklin Park Zoo

Go City's All-Inclusive Pass is the best Boston pass if you're looking for an easy-to-use, flexible way to explore the city whilst also saving money....

1 to 7 days
4.2 (320)
from
$79
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
4.7 (43)

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 • Hotel pickup offered • Free Cancellation
4.7 (43)
from
$108
From Boston: Niagara Falls 2-Day Tour with Overnight Stay

Experience Niagara Falls at its most dramatic on this two-day journey from Boston, featuring a rare nighttime exploration and an optional up-close daytime adventure. Arrive …More

Niagara Falls, USA
4.6 (47)

From Boston: Niagara Falls 2-Day Tour with Overnight Stay

Experience Niagara Falls at its most dramatic on this two-day journey from Boston, featuring a rare nighttime exploration and an optional up-close daytime adventure. Arrive...

2 days • Free Cancellation
4.6 (47)
from
$307
Cape Cod Self-Guided Driving Audio Tour

Explore Cape Cod’s scenic beauty with this self-guided driving tour. Visit the Cape Cod Visitor Center, then ascend Scargo Tower for breathtaking views. Discover Harwich …More

Cape Cod, USA
3.9 (32)

Cape Cod Self-Guided Driving Audio Tour

Explore Cape Cod’s scenic beauty with this self-guided driving tour. Visit the Cape Cod Visitor Center, then ascend Scargo Tower for breathtaking views. Discover Harwich...

3 to 4 hours • Free Cancellation
3.9 (32)
from
$17
Go City: Boston Explorer Pass - Choose 2, 3, 4 or 5 Attractions

Enjoy discounts up to 50%* off regular admission prices with the Boston Explorer Pass. This multi-attraction pass, valid for 30 days after your first use, …More

Boston, USA
3.9 (65)

Go City: Boston Explorer Pass - Choose 2, 3, 4 or 5 Attractions

Enjoy discounts up to 50%* off regular admission prices with the Boston Explorer Pass. This multi-attraction pass, valid for 30 days after your first use,...

1 to 60 days
3.9 (65)
from
$54
Boston to Kennebunkport Day Trip with Optional Trolley Tour

Nothing quite captures the beauty of New England like the Southern Maine Coast. Incredible scenery, lighthouses, history and great food make this trip a "must" …More

Boston, USA
4.8 (166)

Boston to Kennebunkport Day Trip with Optional Trolley Tour

Nothing quite captures the beauty of New England like the Southern Maine Coast. Incredible scenery, lighthouses, history and great food make this trip a "must"...

11 hours • Hotel pickup offered • Free Cancellation
4.8 (166)
from
$135
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
4.6 (22)

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...

7 to 9 hours • Hotel pickup offered • Free Cancellation
4.6 (22)
from
$118
Private Nantucket Beach Fishing Activity with a Guide

Fish and explore the beaches of beautiful Nantucket Island with your native guide, Steve Tuna. Fish hard or simply explore and enjoy the beach. Steve …More

Nantucket, USA
5.0 (25)

Private Nantucket Beach Fishing Activity with a Guide

Fish and explore the beaches of beautiful Nantucket Island with your native guide, Steve Tuna. Fish hard or simply explore and enjoy the beach. Steve...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (25)
from
$675
Spend the Day on Buzzards Bay - Powerboat Cruises

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are …More

Likely to Sell Out
Likely to Sell Out
5.0 (1)

Spend the Day on Buzzards Bay - Powerboat Cruises

Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are...

2 hours • Free Cancellation
5.0 (1)
from
$540
Boston Freedom Trail Private Car Tour

We'll see the sights on Boston's Freedom Trail and get a closer look by leaving the car and walking inside some locations (depends on day …More

Boston, USA
5.0 (1)

Boston Freedom Trail Private Car Tour

We'll see the sights on Boston's Freedom Trail and get a closer look by leaving the car and walking inside some locations (depends on day...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$600
Run 'Boston' Sports Running Tour

Traverse your own 'Mini Boston Marathon' - warm up from the Common to Kenmore and then run the last mile of the marathon route across …More

Boston, USA
5.0 (1)

Run 'Boston' Sports Running Tour

Traverse your own 'Mini Boston Marathon' - warm up from the Common to Kenmore and then run the last mile of the marathon route across...

2 hours • Free Cancellation
5.0 (1)
from
$35
Private Guided Berkshire Mountains Hike with Scenic Views

Experience the Greylock Glen trails alongside a groovy local guide who knows the area's best routes and hidden gems. Instead of worrying about navigation or …More

The Berkshires, USA
5.0 (2)

Private Guided Berkshire Mountains Hike with Scenic Views

Experience the Greylock Glen trails alongside a groovy local guide who knows the area's best routes and hidden gems. Instead of worrying about navigation or...

2 hours • Free Cancellation
5.0 (2)
from
$150
Lost River Gorge and White Mountains Day Tour

Escape Boston for a full day in New Hampshire's White Mountains. During the summer route, explore the caves, waterfalls, bridges, and forest paths of Lost …More

Boston, USA
4.8 (5)

Lost River Gorge and White Mountains Day Tour

Escape Boston for a full day in New Hampshire's White Mountains. During the summer route, explore the caves, waterfalls, bridges, and forest paths of Lost...

7 to 8 hours • Free Cancellation
4.8 (5)
from
$190
Ziplining and Climbing at The Adventure Park on Cape Cod

Are you ready for the best climbing and zip line adventure Cape Cod has to offer? Get outside and into our aerial adventure park to …More

Cape Cod, USA
4.8 (6)

Ziplining and Climbing at The Adventure Park on Cape Cod

Are you ready for the best climbing and zip line adventure Cape Cod has to offer? Get outside and into our aerial adventure park to...

2 hours 30 minutes • Free Cancellation
4.8 (6)
from
$63
eFoil Lessons on Cape Cod

Entering the 5th year of operation, we are the Cape’s top destination for eFoiling. Whether you are a total beginner or an experienced boarder, we …More

Cape Cod, USA
5.0 (8)

eFoil Lessons on Cape Cod

Entering the 5th year of operation, we are the Cape’s top destination for eFoiling. Whether you are a total beginner or an experienced boarder, we...

1 hour 30 minutes • Free Cancellation
5.0 (8)
from
$210
North of Boston Island Lighthouse Kayak Tour

Unlike typical kayak tours, North of Boston Island Lighthouse Tour is a refined, personalized coastal experience. Your expertly trained guides combine deep knowledge of local …More

5.0 (3)

North of Boston Island Lighthouse Kayak Tour

Unlike typical kayak tours, North of Boston Island Lighthouse Tour is a refined, personalized coastal experience. Your expertly trained guides combine deep knowledge of local...

2 hours • Free Cancellation
5.0 (3)
from
$90

Frequently Asked Questions

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

Recent tour reviews
Very pleasant day
New York City
Boston: Martha’s Vineyard ICONIC Small Group Day Escape w/Ferry
H1367ZSkellyb, Sep 2026
Very pleasant day
This was a great day trip. Willy, our driver from Boston to the ferry took very good care of us. Made sure we had drinks and snacks for the ride and that we knew where we were going to catch the ferry and where he would be when we got back. He also contacted us during our time on Martha's Vineyard to ensure we knew where we were catching our tour bus and what time we needed to catch the ferry back.Our guide on Martha's Vineyard was awesome. Liz was very knowledgeable and had history on the island. She wove that personal knowledge into her narrating and it was very interesting. Before catching the ferry, we had time for lunch and a bit of shopping.Plan on a whole day for this tour. We left at 6am and got back to our hotel around 6pm.
Read more
Wandering through St Ann 202609
New York City
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Explore591777, Sep 2026
Wandering through St Ann 202609
This was very useful. The guide had us turn down some streets we never would have gone because there were "private" signs up for roads that were not private. There are sights we certainly would not have seen without it.
Read more
Boston to Kennebunkport Day Trip with Trolley Tour
New York City
Boston to Kennebunkport Day Trip with Optional Trolley Tour
Kelly_P, Sep 2026
Boston to Kennebunkport Day Trip with Trolley Tour
The Boston to Kennebunkport Day Trip with Trolley Tour was amazing. A beautiful place with lots to see. Jennifer tour guide and driver was amazing, both informative and funny.
Read more
Lovely trip
New York City
Boston: Martha’s Vineyard ICONIC Small Group Day Escape w/Ferry
Tanya_W, Sep 2026
Lovely trip
Paco picked us up for the first part of the tour and was very informative a very good driver, was considerate of everyone’s needs The second part of our trip was by Liz her knowledge of the area is indeed impressive the Aquinas cliffs were impressive and the gingerbread cottages were beautiful
Read more
Fun time even at low tide
New York City
Kayak The Creek Nature Tour
dyc528, Sep 2026
Fun time even at low tide
Great way to experience another part of the Cape other than the ocean. Winding path through the inlet out to Cape Cod Bay. Relaxing with a great, helpful guide. Highly recommend!
Read more
Great tour and guide, Willy!
New York City
Portland: Lighthouse, Old Port and Park 1-Day Tour from Boston
RobinG441, Sep 2026
Great tour and guide, Willy!
What a great day! Every stop was incredible. Willy did a phenomenal job! He drove us safely, kept us entertained, made sure we had bathroom breaks, and supplied us with snacks and water! What a fantastic day. Highly recommend this tour and Willy!
Read more
Beautiful Scenic Drive
New York City
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Aboli_A, Sep 2026
Beautiful Scenic Drive
Whale watching was my favorite activity of our time on the Cape. This was runner up! I followed the directions to have the app and tour downloaded while I was on WiFi before setting out. While we did have to back up/turn around after missing a turn or two more than if I had my regular maps app on, it was still a good experience and we saw places we otherwise never would have seen - many hidden beaches and coves and stunning seaside mansions. At this price point per vehicle, this tour is a no brainer if you have an extra day.
Read more
Like a true “Swiss Family Robinson Treehouse”!
New York City
Lost River Gorge and White Mountains Day Tour
michmich805, Sep 2026
Like a true “Swiss Family Robinson Treehouse”!
This was really a terrific experience! We wanted to go on a day trip from Boston, but it wasn’t available, so we rented a car and spent the night in the area to go first thing in the morning. All I can say is “WOW”! For the real experience, be prepared to crawl in small caves. (I didn’t do that part). The stairways are spectacular themselves, in and through the gorgeous gorges and spectacular scenery. It takes about an hour to walk through the whole things, (lots of stairs)- good cardio for the morning!
Read more
Paco the best....
New York City
From Boston: Niagara Falls 2-Day Tour with Overnight Stay
David_E, Sep 2026
Paco the best....
It was very informative and well organized with frequent reminders of plans ahead of times. Paco the tour guide provided excellent service and was very well informed and engaging.
Read more
Long Weekend
New York City
Go City: Boston Explorer Pass – Choose 2, 3, 4 or 5 Attractions
928royf, Sep 2026
Long Weekend
Great experience with Go City providing access to over 40 attractions.
Read more
Long Weekend
New York City
Boston Pass: 40+ Things To Do – Includes Franklin Park Zoo
928royf, Sep 2026
Long Weekend
Having visited various city's in the past I knew it was important to prebook some type of City pass for the various sight seeing opportunities in Boston, which is what we did with Go City. The 40+ pass allowed us to visit everything we wanted to plus a few other places while being good value and saving us money. The only thing missing from the pass was the tube/train and bus pass which was a Charlie ticket, that gave us 7 days unlimited travel, but we had to arrange this separately.
Read more
Niagara Falls 2 Day trip
New York City
From Boston: Niagara Falls 2-Day Tour with Overnight Stay
elenasB7153JI, Sep 2026
Niagara Falls 2 Day trip
We had a wonderful trip with Sam, who was the best and truly made the trip unforgettable! Everything was very well organized and on time, and the three stops along the way made the long drive much easier. We saw all the main attractions, including the firework, and managed to fit everything into two days. The hotel was good, with a beautiful sunset view over the river. 😊
Read more
Fun Kayak Tour
New York City
Kayak The Creek Nature Tour
MarioPerez44, Sep 2026
Fun Kayak Tour
Great experience and we highly recommend it.
Read more
Excellent value for a family trip.
New York City
Boston Pass: 40+ Things To Do – Includes Franklin Park Zoo
GoPlaces43600078892, Sep 2026
Excellent value for a family trip.
We stayed in Boston for a week and really got our moneys worth from this pass. It was easy to use, the app was brilliant to help us decide which attractions we would visit. Such great value if you’re going for a longer trip and plan on going hard on the sights.
Read more
I had an amazing hiking...
New York City
Private Guided Berkshire Mountains Hike with Scenic Views
hamed_a, Aug 2026
I had an amazing hiking...
I had an amazing hiking experience! The whole trip was peaceful, relaxing, and incredibly enjoyable. The scenery was absolutely beautiful, with breathtaking views throughout the hike, and we were lucky to have perfect weather.Our guide was very friendly, welcoming, and flexible, which made the experience even better. Everything felt relaxed and never rushed, giving us plenty of time to enjoy the surroundings and take in the views.Overall, it was a wonderful experience and one of the most enjoyable hikes I’ve done. I would definitely recommend it to anyone looking for a beautiful and peaceful outdoor adventure!
Read more
Perfect experience!
New York City
Private Guided Berkshire Mountains Hike with Scenic Views
staceystokes2015, Aug 2026
Perfect experience!
Jeff took me to a spectacular off the beaten track hike on our first outing. His directions were perfect and he was so accommodating and sensitive to my interests and physical abilities. I wanted a guide because I'm on my own and he made me feel completely comfortable. On our second hike he took me to Mount Greylock and took me through a variety of woodlands. I can't wait till next year to do more hikes with him.
Read more
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