Pleasant Bay Boat Tours
5.0
/5
(10 reviews)
Kescayogansett Road 37, Orleans, MA 02653, United States–
Pleasant Bay Boat Tours
Orleans, MA, United States
–
20 feet
6
5.0
/5
(10 reviews)
THANK YOU TO ALL THE SUMMER 2025 PASSENGERS. I ENJOYED SHARING THE BEAUTY OF CAPE COD FROM THE WATER. I AM CLOSED FOR THE SEASON. SEE YOU NEXT YEAR!
Welcome to your premier source for unforgettable boat charters. Take in the splendor of the Pleasant Bay's sparkling water, salt ponds, and wildlife from our clean and comfortable 20-foot deck boat. We offer two-hour tours and custom charters. The choice is yours!
Departure is from a private shore on Mayflower point in South Orleans with parking at a private residence and a five minute walk along a dirt road to the boat. Details provided after booking.
Notes: 1. There are no restrooms at the parking location or on the boat. For those coming from the south, the Speedway gas/convenience store on Rt. 28 in South Orleans has restrooms. 2. Ignore "+ taxes and fees when booking." MA does not tax tours. 3. Because charter boat insurance only covers incidents while on the boat, all passengers leaving the boat to swim, walk the beach, etc., must sign a liability waiver for themselves and any minors for whom they are responsible.
Customer reviews
5.0
(10 reviews)
5
10
4
0
3
0
2
0
1
0
5.0
Boat & equipment
5.0
Captain & crew
5.0
Boating Experience
Customers' gallery (10)
+4
All reviews (10)
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Showing 1 – 5 of 10 reviews
Diana Levine
5.0
Verified
Captain James’ Was Great!!
1 Hour – Evening Cruise (5PM) on August 12, 2025 • 4 adults • 2 children
Our family (3 generations) had a fun adventure for all. Our 13 year old grandson rated Capt. James a “ 10/10 I would do it again. It was Great. Our Guide was very informative and knowledgeable. He gave us an awesome tour. “ Our 11 year old granddaughter said, “ I 100% agree with my brother. I would also like to add that the variation in speed was very nice. “
We highly recommend Capt. James,
The Levine Family
Response from Captain
August 14, 2025
Thank you, Diana! I had a great time with your lovely family.
0
Holly Hillburn
5.0
Verified
Best part of our vacation!
9 AM 2 hr. Tour on July 16, 2025 • 2 adults • 3 children
This was an awesome experience! Our family of five including three kids (10, 8 & 6) had an amazing time. The boat was beautiful and captain James was so accommodating. He had several sizes of life vests for the kids and made everything easy. Highly recommend booking!!! This will be on repeat for next year's vacation on the cape!
0
Rosemary Duran
5.0
Verified
High Point of the Week
3 PM 2 hr. Tour on August 15, 2025 • 3 adults • 3 children
Captain James brought us from lovely Pleasant Bay to Chatham Lighthouse. On the way we stopped and sat closely to a pod of seals who seamed as interested in us as we were with them, with their heads fully out of the water. James knows much about sea birds, the islands and mainline coast.
Response from Captain
August 17, 2025
Thank you!
0
Desiree Gotlibowski
5.0
Verified
Returning for another trip!
9 AM 2 hr. Tour on August 13, 2025 • 4 adults
I loved the experience with Captain James and booked another trip! My girlfriends and I went out paddle boarding and he was able to find seals for us and accommodate all of our preferences! He’s knowledgeable and helpful and gave us a great experience! Can’t wait for next year!
Response from Captain
August 15, 2025
Thank you, Desiree. I am honored that you are my first repeat passenger!
0
Emily Colter
5.0
Verified
Perfect day!
12 PM 2 hr. Tour on August 10, 2025 • 5 adults • 1 child
We’ve been coming to the Cape for 40 years but Captain James showed us the Cape like we’ve never seen! It was incredible to weave in and out of the coast line taking in all the natural beauty! And the seals were are favorite! Best afternoon, would highly recommend to anyone!
Response from Captain
August 14, 2025
Really appreciate it, Emily. I had a great time with your family. All the best, James.
0
Trip availability and prices
Trip Date:
Days:
Group Size:
Select date to see availability
May 2026
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
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Number of days
1
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9 AM 2 hr. Tour
FREE Cancellation 1 day notice
2 Hour Trip
starts at 9:00 AM
Seasonal trip
Jun 10 - Aug 30
US $300
Private tour: up to 6 people
US $300
Private tour: up to 6 people
12 PM 2 hr. Tour
FREE Cancellation 1 day notice
2 Hour Trip
starts at 12:00 PM
Seasonal trip
Jun 10 - Aug 30
US $300
Private tour: up to 6 people
US $300
Private tour: up to 6 people
3 PM 2 hr. Tour
FREE Cancellation 1 day notice
2 Hour Trip
starts at 3:00 PM
Seasonal trip
Jun 10 - Aug 30
US $300
Private tour: up to 6 people
US $300
Private tour: up to 6 people
Custom Charter
FREE Cancellation 1 day notice
4 Hour Trip
starts at 10:00 AM
US $600
Private tour: up to 6 people
US $600
Private tour: up to 6 people
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Customer reviews
5.0
(10 reviews)
5
10
4
0
3
0
2
0
1
0
5.0
Boat & equipment
5.0
Captain & crew
5.0
Boating Experience
Customers' gallery (10)
+4
All reviews (10)
Filter
Filter
Sort by: Featured
Featured
Showing 1 – 5 of 10 reviews
Diana Levine
5.0
Verified
Captain James’ Was Great!!
1 Hour – Evening Cruise (5PM) on August 12, 2025 • 4 adults • 2 children
Our family (3 generations) had a fun adventure for all. Our 13 year old grandson rated Capt. James a “ 10/10 I would do it again. It was Great. Our Guide was very informative and knowledgeable. He gave us an awesome tour. “ Our 11 year old granddaughter said, “ I 100% agree with my brother. I would also like to add that the variation in speed was very nice. “
We highly recommend Capt. James,
The Levine Family
Response from Captain
August 14, 2025
Thank you, Diana! I had a great time with your lovely family.
0
Holly Hillburn
5.0
Verified
Best part of our vacation!
9 AM 2 hr. Tour on July 16, 2025 • 2 adults • 3 children
This was an awesome experience! Our family of five including three kids (10, 8 & 6) had an amazing time. The boat was beautiful and captain James was so accommodating. He had several sizes of life vests for the kids and made everything easy. Highly recommend booking!!! This will be on repeat for next year's vacation on the cape!
0
Rosemary Duran
5.0
Verified
High Point of the Week
3 PM 2 hr. Tour on August 15, 2025 • 3 adults • 3 children
Captain James brought us from lovely Pleasant Bay to Chatham Lighthouse. On the way we stopped and sat closely to a pod of seals who seamed as interested in us as we were with them, with their heads fully out of the water. James knows much about sea birds, the islands and mainline coast.
Response from Captain
August 17, 2025
Thank you!
0
Desiree Gotlibowski
5.0
Verified
Returning for another trip!
9 AM 2 hr. Tour on August 13, 2025 • 4 adults
I loved the experience with Captain James and booked another trip! My girlfriends and I went out paddle boarding and he was able to find seals for us and accommodate all of our preferences! He’s knowledgeable and helpful and gave us a great experience! Can’t wait for next year!
Response from Captain
August 15, 2025
Thank you, Desiree. I am honored that you are my first repeat passenger!
0
Emily Colter
5.0
Verified
Perfect day!
12 PM 2 hr. Tour on August 10, 2025 • 5 adults • 1 child
We’ve been coming to the Cape for 40 years but Captain James showed us the Cape like we’ve never seen! It was incredible to weave in and out of the coast line taking in all the natural beauty! And the seals were are favorite! Best afternoon, would highly recommend to anyone!
Response from Captain
August 14, 2025
Really appreciate it, Emily. I had a great time with your family. All the best, James.
0
FAQs about Pleasant Bay Boat Tours
What the boat is like
Boat category
Speed boatsBoat type
Deck boatBoat manufacturer
Nautic StarBoat Model
230 SCYear built
2018Boat length
20 ftCapacity
6 persons