Pleasant Bay Boat Tours
Pleasant Bay Boat Tours
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
Rating summary
Photos & videos by reviewers (10)
+7Customer rating
Customers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Aug 12, 2025
1 Hour – Evening Cruise (5PM)
Captain James’ Was Great!!
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
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....
Captain replied
Jul 16, 2025
9 AM 2 hr. Tour
Best part of our vacation!
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!
This was an awesome experience! Our family of five including three kids (10, 8 & 6) had an amazing time. The boat was beautiful...
Aug 15, 2025
3 PM 2 hr. Tour
High Point of the Week
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.
Captain James brought us from lovely Pleasant Bay to Chatham Lighthouse. On the way we stopped and sat closely to a pod of seals...
Captain repliedAug 13, 2025
9 AM 2 hr. Tour
Returning for another trip!
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!
I loved the experience with Captain James and booked another trip! My girlfriends and I went out paddle boarding and he was able...
Captain replied
Aug 10, 2025
12 PM 2 hr. Tour
Perfect day!
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!
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...
Captain repliedTrip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (10)
+7Customer rating
Customers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Experience:
Equipment
Crew
Overall
Captain James’ Was Great!!
1 Hour – Evening Cruise (5PM) on August 12, 2025
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
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
Experience:
Equipment
Crew
Overall
Best part of our vacation!
9 AM 2 hr. Tour on July 16, 2025
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!
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!
Experience:
Equipment
Crew
Overall
High Point of the Week
3 PM 2 hr. Tour on August 15, 2025
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.
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.
Experience:
Equipment
Crew
Overall
Returning for another trip!
9 AM 2 hr. Tour on August 13, 2025
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!
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!
Experience:
Equipment
Crew
Overall
Perfect day!
12 PM 2 hr. Tour on August 10, 2025
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!
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!