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Top Massachusetts Private Sightseeing Tours

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Massachusetts Tours

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Self-Guided Smartphone Ghost Walking Tour in Salem

This is a Smartphone Guided ghost tour on our walking tour app. Go to the Ropes Mansion, press play and put your phone in your …More

Salem, USA
4.3 (241)

Self-Guided Smartphone Ghost Walking Tour in Salem

This is a Smartphone Guided ghost tour on our walking tour app. Go to the Ropes Mansion, press play and put your phone in your...

40 to 50 minutes • Free Cancellation
4.3 (241)
from
$8
Cape Cod & Provincetown Self-Guided Driving & Walking Audio Tour

Purchase one tour per car, not per person. Everyone listens together! Explore all that Cape Cod has to offer with this self-guided driving tour, from …More

Cape Cod, USA
4.1 (202)

Cape Cod & Provincetown Self-Guided Driving & Walking Audio Tour

Purchase one tour per car, not per person. Everyone listens together! Explore all that Cape Cod has to offer with this self-guided driving tour, from...

3 to 4 hours • Free Cancellation
4.1 (202)
from
$25
Ultimate Historic Salem and Witch Trials Self-Guided Walking Tour

Uncover the truth behind the infamous Salem Witch Trials with this self-guided walking tour of Salem, Massachusetts! This quaint and picturesque town hides a seriously …More

Salem, USA
4.4 (74)

Ultimate Historic Salem and Witch Trials Self-Guided Walking Tour

Uncover the truth behind the infamous Salem Witch Trials with this self-guided walking tour of Salem, Massachusetts! This quaint and picturesque town hides a seriously...

1 to 2 hours • Free Cancellation
4.4 (74)
from
$17
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's Beacon Hill Underground Railroad Audio Walking Tour

Discover Beacon Hill's Underground Railroad history while walking its cobbled stones streets. On this historic adventure you'll see the old hidden alley's slave catchers once …More

Boston, USA
4.7 (29)

Boston's Beacon Hill Underground Railroad Audio Walking Tour

Discover Beacon Hill's Underground Railroad history while walking its cobbled stones streets. On this historic adventure you'll see the old hidden alley's slave catchers once...

45 to 55 minutes • Free Cancellation
4.7 (29)
from
$10
Private 1.5-Hour Freedom Trail Walking Tour with Costumed Guide

A 90-minute walking tour of the Freedom Trail that covers the first 11 historic sites. It starts in Boston Common at the Visitor Information Center …More

Boston, USA
4.8 (43)

Private 1.5-Hour Freedom Trail Walking Tour with Costumed Guide

A 90-minute walking tour of the Freedom Trail that covers the first 11 historic sites. It starts in Boston Common at the Visitor Information Center...

90 to 240 minutes • Free Cancellation
4.8 (43)
from
$450
Lexington & Concord Self-Guided Driving & Walking Audio Tour

Discover the thrilling events behind the “shot heard ‘round the world” with this self-guided driving/walking tour through Lexington and Concord. Follow the path of the …More

4.2 (69)

Lexington & Concord Self-Guided Driving & Walking Audio Tour

Discover the thrilling events behind the “shot heard ‘round the world” with this self-guided driving/walking tour through Lexington and Concord. Follow the path of the...

2 to 3 hours • Free Cancellation
4.2 (69)
from
$15
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
Self Guided Audio Tour 'Hawthorne's Haunts' Haunted Walking Tour Salem

This is a Smartphone Guided ghost tour on the WalknTours app. Go anytime, the tour never expires and you can take it as many times …More

Salem, USA
4.9 (7)

Self Guided Audio Tour 'Hawthorne's Haunts' Haunted Walking Tour Salem

This is a Smartphone Guided ghost tour on the WalknTours app. Go anytime, the tour never expires and you can take it as many times...

45 to 55 minutes • Free Cancellation
4.9 (7)
from
$5
Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour

Go at your own pace, anytime! It's your tour. On our historic walking tour of the Edgartown, you will see the iconic sights and secret …More

Martha's Vineyard, USA
4.3 (15)

Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour

Go at your own pace, anytime! It's your tour. On our historic walking tour of the Edgartown, you will see the iconic sights and secret...

60 to 75 minutes • Free Cancellation
4.3 (15)
from
$10
Salem Full Day Private Tour from Boston

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past …More

Likely to Sell Out
Likely to Sell Out
Boston, USA
5.0 (5)

Salem Full Day Private Tour from Boston

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past...

8 hours • Hotel pickup offered • Free Cancellation
5.0 (5)
from
$155
Wellfleet Harbor Seal Cruise Small Group Boat Tour on Cape Cod

Enjoy a private seal-watching crossing with only your group aboard. We’ll explore at a relaxed pace, with time to linger when conditions allow and observe …More

Cape Cod, USA
4.6 (7)

Wellfleet Harbor Seal Cruise Small Group Boat Tour on Cape Cod

Enjoy a private seal-watching crossing with only your group aboard. We’ll explore at a relaxed pace, with time to linger when conditions allow and observe...

1 hour • Free Cancellation
4.6 (7)
from
$306
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
Cambridge, Lexington, & Concord: Private Revolutionary War Tour

Immerse yourself in this Revolutionary War full-day driving tour which will take you on a journey to explore the significant sites of the American Revolution. …More

Boston, USA
5.0 (1)

Cambridge, Lexington, & Concord: Private Revolutionary War Tour

Immerse yourself in this Revolutionary War full-day driving tour which will take you on a journey to explore the significant sites of the American Revolution....

6 hours • Hotel pickup offered
5.0 (1)
from
$160
Chatham Bites and Sights Walking Guided Food Tasting Tour

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by …More

Likely to Sell Out
Likely to Sell Out
Cape Cod, USA
5.0 (86)

Chatham Bites and Sights Walking Guided Food Tasting Tour

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by...

3 hours • Free Cancellation
5.0 (86)
from
$108
Provincetown West End History Tour

Join Your guide Cathy and embark on a captivating journey through Provincetown’s West End, where the sands of time meet the tides of history. This …More

Cape Cod, USA
4.9 (7)

Provincetown West End History Tour

Join Your guide Cathy and embark on a captivating journey through Provincetown’s West End, where the sands of time meet the tides of history. This...

1 hour 30 minutes • Free Cancellation
4.9 (7)
from
$68
Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)

-Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. -Relax and enjoy …More

Martha's Vineyard, USA
4.9 (91)

Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)

-Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. -Relax and enjoy...

3 hours • Free Cancellation
4.9 (91)
from
$550
Boston Massachusetts Private Photography Tour

We are soulful photographers. Our objective is to create absolutely stunning photographs for you that you will cherish and proudly share with your friends and …More

Boston, USA
5.0 (3)

Boston Massachusetts Private Photography Tour

We are soulful photographers. Our objective is to create absolutely stunning photographs for you that you will cherish and proudly share with your friends and...

1 hour • Free Cancellation
5.0 (3)
from
$130
Private Cultural Walk Through Historic Salem’s Legends

This private cultural walking tour reveals the fascinating heritage and enduring mysteries of Salem, one of America’s most historic and storied destinations. Explore the city's …More

Salem, USA
5.0 (3)

Private Cultural Walk Through Historic Salem’s Legends

This private cultural walking tour reveals the fascinating heritage and enduring mysteries of Salem, one of America’s most historic and storied destinations. Explore the city's...

2 hours • Free Cancellation
5.0 (3)
from
$299
Nantucket Self-Guided Audio Walking Tour: Beyond the Cobblestones

Explore historic downtown Nantucket on a self-guided audio walking tour. Follow a roughly 2-mile route as stories and directions play automatically along the way. Hear …More

Nantucket, USA
4.2 (11)

Nantucket Self-Guided Audio Walking Tour: Beyond the Cobblestones

Explore historic downtown Nantucket on a self-guided audio walking tour. Follow a roughly 2-mile route as stories and directions play automatically along the way. Hear...

2 to 3 hours • Free Cancellation
4.2 (11)
from
$10

Frequently Asked Questions

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

Recent tour reviews
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
Great way to see Chatham
New York City
Chatham Bites and Sights Walking Guided Food Tasting Tour
peterwf2024, Sep 2026
Great way to see Chatham
Had a great time on our tour Our guide Kathy was wonderful Would definitely recommend this
Read more
Fabulous food tour!
New York City
Chatham Bites and Sights Walking Guided Food Tasting Tour
josk672, Sep 2026
Fabulous food tour!
Excellent tour! I try to do a good tour in each new city I visit and this was one of the best! Kathy was a great guide, the food was delicious with a nice variety. Aplaya Philippine restaurant was an unexpected delight! Buffy’s Ice Cream Sandwiches made a perfect, delicious finale! I highly recommend this tour!
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
Craig was a fantastic...
New York City
Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)
Bobby_A, Sep 2026
Craig was a fantastic...
Craig was a fantastic guide. He was in communication with us before we arrived so he knew the ferry was dropping us off at a different terminal than was the original pick up point. Had a great and informative 3 hour tour of the entire island. Vehicle was clean and comfortable. Craig was very friendly and we hope to see him in Myrtle Beach for a visit.
Read more
Sweet history lesson
New York City
Private Open-Air Pedicab Tour in Provincetown
ArnieR_13, Sep 2026
Sweet history lesson
Very fun experience and a good introduction to Provincetown. Advice: some sort of amplifier or speaker for the driver would be helpful. Difficult to hear at times.
Read more
Very good tour & very good value
New York City
Self-Guided Smartphone Ghost Walking Tour in Salem
elizabethsY5124WS, Sep 2026
Very good tour & very good value
It was a really good tour. It was very informative. The directions were very precise about which way to face and how far to walk. We loved the flexibility of being able to stop and start as often as we needed or wanted to. We paused a few times to shop and once to just rest along the way. I felt like we got every bit as good of a tour as we would have with a group tour and paid guide, but we could probably hear better since there were only three of us. By the way, we only purchased one tour and just listened to it from my speakerphone. The only downside was that it ran down my phone battery considerably. So in hindsight, I would’ve brought a charger with me. Something to consider if purchasing only 1 (vs 3) might be that if the crowds had been any larger we may not have been able to hear well, but since we did this in September, all 3 of us were able to hear just fine.
Read more
Great Ptown West End Tour with Cathy
New York City
Provincetown West End History Tour
Cathy_C, Sep 2026
Great Ptown West End Tour with Cathy
Cathy was an excellent tour guide. She knew the history and brought it to life. Good pace for our group and she was attentive to our energy level. Lots of beautiful and interesting sites on the tour. Would definitely recommend it.
Read more
Great experience!
New York City
Ultimate Historic Salem and Witch Trials Self-Guided Walking Tour
Lisa_G, Sep 2026
Great experience!
Exceptionally knowledgeable and dedicated staff. Very enjoyable tour -- even for my second time! Read the book, watch the movie, do this tour!
Read more
Best Walking Tour
New York City
Self-Guided Smartphone Ghost Walking Tour in Salem
Colleen_C, Sep 2026
Best Walking Tour
Very informative & fun. Go at your own pace & enjoy the sites. Would do it again! Wear comfortable shoes though.
Read more
Great tour with Craig
New York City
Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)
Russell_S, Sep 2026
Great tour with Craig
Craig is an excellent guide. Knowledgeable and humorous. My wife and I very much enjoyed our tour of Martha’s Vineyard. We were impressed with all the detailed information that Craig had to share. His vehicle was spotless and he drove safely.
Read more
Great Audioguide
New York City
Lexington & Concord Self-Guided Driving & Walking Audio Tour
663ferencp, Sep 2026
Great Audioguide
Great Audio guide, part driving part walkingf but always interesting information. Very precise instructions. I suggest taking an airpod with you for when you are walking
Read more
Provincetown Pedicab
New York City
Private Open-Air Pedicab Tour in Provincetown
Rich_M, Aug 2026
Provincetown Pedicab
Very knowledgeable and friendly guide, he was a lot of fun. We particularly liked seeing the sea coast and dunes
Read more
Enjoyable - own time own pace
New York City
Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour
Trail13374549340, Aug 2026
Enjoyable - own time own pace
Really great idea! Loved going on our own time and pace. I wasn’t feeling well from over drinking the night before. I loved not having to be somewhere at a particular time. And we could take a break when we wanted. Great information and easy to use! Loved doing the walking tour app!!!
Read more
The best!
New York City
Wellfleet Harbor Seal Cruise Small Group Boat Tour on Cape Cod
Rachel_I, Aug 2026
The best!
We had an awesome tour with the Packet Boat and Captain Brandon! He is super knowledgeable and fun, was great with our kiddos— they had an absolute blast. Couldn’t recommend more!
Read more
Private Seal Watching Cruise in Wellfleet, MA
New York City
Wellfleet Harbor Seal Cruise Small Group Boat Tour on Cape Cod
Bradley_W, Aug 2026
Private Seal Watching Cruise in Wellfleet, MA
This was a really cool and unique experience. Brandon was really a great captain and guide for the whole trip. We had perfect weather for the trip, so we got to see and hear the seals from the boat with perfect clarity. We booked the 4:30 time slot during low-tide and got to see the most seals! There had to be 50 or 60 seals just hanging out, singing to each other and keeping tabs on us. I got a lot of great seal eye contact pics. We saw some dolphins that were caught by the shallows and were being wrangled and guided to open water by a small boat, so we got to see more than just seals. No sharks though. Maybe next time. The kids did get to steer the boat a bit, and that was a lot of fun for them! I would definitely go again, the entire trip was such a nice part of the day. Brandon also suggested a restaurant down the road to check out and that was great, too! Thanks Cool Destinations and Brandon for the suggestion and the easy-to-book trip. If you've got any questions about more details, reach out to Brandon and have a conversation with him.
Read more
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