Captain
Ken Middleton

Member since October 2024 Honolulu, United States
Background
Sailed over from Seattle, WA in the 1980's to start Tradewind Charters. With a fleet of 3 charter vessels based in Kewalo Harbor, we specialize in private, upscale charters for 2-29 guests.
Techniques
Private snorkeling, whale watching, sunset cruises, weddings and receptions at sea, memorial services at sea.

Hey, I'm Captain Ken Middleton

Honolulu, United States
Background
Sailed over from Seattle, WA in the 1980's to start Tradewind Charters. With a fleet of 3 charter vessels based in Kewalo Harbor, we specialize in private, upscale charters for 2-29 guests.
Techniques
Private snorkeling, whale watching, sunset cruises, weddings and receptions at sea, memorial services at sea.
20
Reviews

My Listings

Tradewinds Charters – Aloha Kai

Excellent
5.0 / 5
(2 reviews)
Honolulu
 Instant Confirmation
trips from US $1,500

Tradewinds Charters – Sea Scape

Excellent
5.0 / 5
(8 reviews)
Honolulu
 Instant Confirmation
trips from US $1,495

Tradewinds Charters – My Sunshine

Excellent
4.7 / 5
(10 reviews)
Honolulu
 Instant Confirmation
trips from US $695

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 20 reviews
See details
Boat
Excellent
4.7 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (6)
Dolphins!
Memorial ash release for 3 family members
Memorial ash release for 3 family members
+3
Customer rating
16
2
1
0
0
Customers claimed
Good experience
83%
Friendly captain
100%
Recommend this charter
90%
Appropriate for children
100%
Satisfied with the boat
89%
Sort by:
Featured  
Showing:
5 of 20 reviews
Craig E.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Very knowledgeable crew!

VERIFIED   NEW  3 Hour–Cruise&Snorkel (1-12 people) on May 12, 2026
The crew was a big help in walking us through the process for spreading my wife’s ashes as she wished. It made a difficult...
Craig E. recommends Tradewinds Charters – Sea Scape
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Craig E. recommends Tradewinds Charters – Sea Scape
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Sydney S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Such a great crew and experience!

VERIFIED   2 Hr Trip – Sunset Cruise on February 13, 2026
The captain and crew were so kind, organized, and welcoming. We had a full boat of 20-30 somethings and they got us all checked...
Sydney S. recommends Tradewinds Charters – Aloha Kai
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You and 1 other person found this review helpful
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Brittney T.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Memorial ash release for 3 family members

VERIFIED   2 Hr Trip – Sunset Cruise on August 1, 2025
We booked last minute due to our previous booking being canceled due to wind.  They were so accommodating and kind. The captain...
Brittney T. recommends Tradewinds Charters – Aloha Kai
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Brittney T. recommends Tradewinds Charters – Aloha Kai
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Kevin M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great trip

VERIFIED   3 Hour – Cruise&Snorkel (2 PM) on December 4, 2025
Wes was great, he found the wildlife we were looking for and was a gracious host in general.  Highly recommend this tour.
Kevin M. recommends Tradewinds Charters – My Sunshine
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Kevin M. recommends Tradewinds Charters – My Sunshine
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Kevin S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Dolphins!

VERIFIED   3 Hour – Cruise&Snorkel (8 AM) on January 24, 2026
Great time with Captain Wes. He sailed us right next to a pod of dolphins, fantastic experience.
Kevin S. recommends Tradewinds Charters – My Sunshine
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Kevin S. recommends Tradewinds Charters – My Sunshine
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