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)

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.

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. For those coming from other directions, there are public restrooms at 44 Main Street in Orleans. 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.

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.

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. For those coming from other directions, there are public restrooms at 44 Main Street in Orleans. 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.

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Customer reviews

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Rating

5.0
(10 reviews)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

Customers' gallery (10)

All reviews (10)

Showing 15 of 10 reviews
Diana Levine
Diana Levine
us
Boston, MA, US
Member since 2025
5.0
Verified
Captain James’ Was Great!!
1 Hour – Evening Cruise (5PM) on August 12, 20254 adults2 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.
Rosemary Duran
Rosemary Duran
us
New York, US
Member since 2025
5.0
Verified
High Point of the Week
3 PM 2 hr. Tour on August 15, 20253 adults3 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!
Desiree Gotlibowski
Desiree Gotlibowski
Repeat angler
us
Connecticut, US
Member since 2025
2 trips
5.0
Verified
Returning for another trip!
9 AM 2 hr. Tour on August 13, 20254 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!
Emily Colter
Emily Colter
us
Connecticut, US
Member since 2025
5.0
Verified
Perfect day!
12 PM 2 hr. Tour on August 10, 20255 adults1 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.
J S
J S
us
Rhode Island, US
Member since 2025
5.0
Lunch on Pleasant Bay
Custom Charter on July 28, 2025
Fun to tour Pleasant Bay with Captain Jamie! Thank you for a great experience!

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
July 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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Almost there...
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 $325
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 $325
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 $325
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
There are 8 people looking at this charter.

Customer reviews

Loading...

Rating

5.0
(10 reviews)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

Customers' gallery (10)

All reviews (10)

Showing 15 of 10 reviews
Diana Levine
Diana Levine
us
Boston, MA, US
Member since 2025
5.0
Verified
Captain James’ Was Great!!
1 Hour – Evening Cruise (5PM) on August 12, 20254 adults2 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.
Rosemary Duran
Rosemary Duran
us
New York, US
Member since 2025
5.0
Verified
High Point of the Week
3 PM 2 hr. Tour on August 15, 20253 adults3 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!
Desiree Gotlibowski
Desiree Gotlibowski
Repeat angler
us
Connecticut, US
Member since 2025
2 trips
5.0
Verified
Returning for another trip!
9 AM 2 hr. Tour on August 13, 20254 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!
Emily Colter
Emily Colter
us
Connecticut, US
Member since 2025
5.0
Verified
Perfect day!
12 PM 2 hr. Tour on August 10, 20255 adults1 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.
J S
J S
us
Rhode Island, US
Member since 2025
5.0
Lunch on Pleasant Bay
Custom Charter on July 28, 2025
Fun to tour Pleasant Bay with Captain Jamie! Thank you for a great experience!

FAQs about Pleasant Bay Boat Tours

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What the boat is like

Boat category
Speed boats
Boat type
Deck boat
Boat manufacturer
Nautic Star
Boat Model
230 SC
Year built
2018
Boat length
20 ft
Capacity
6 persons
Engine model
Yamaha
Max crusing speed
30 knots
Powered by
1 x 150HP
Engine Type
Outboard
Fuel Type
Gas
Boat category
Speed boats
Boat type
Deck boat
Boat manufacturer
Nautic Star
Boat Model
230 SC
Year built
2018
Boat length
20 ft
Capacity
6 persons
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