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.
22
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
(9 reviews)
Honolulu
 Instant Confirmation
trips from US $1,495

Tradewinds Charters – My Sunshine

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

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 22 reviews
See details
Boat
Excellent
4.7 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (10)
Amazing experience! Highly recommended
Amazing experience! Highly recommended
Amazing experience! Highly recommended
+7
Customer rating
18
2
1
0
0
Customers claimed
Good experience
88%
Friendly captain
100%
Recommend this charter
91%
Appropriate for children
100%
Satisfied with the boat
91%
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Featured  
Showing:
5 of 22 reviews
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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Carlos W.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Ash spreading ceremony

VERIFIED   2 Hour–Sunset Cruise on June 22, 2025
Excellent experience. Crew was extremely respectful. Went out of their way to show us some spotted eagle rays that swam along...
Carlos W. recommends Tradewinds Charters – Sea Scape
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Beckee J.

The captain canceled

VERIFIED   January 1, 2026
The charter operator canceled on trip date. This is an automated posting.
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Micah H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Yessah!

VERIFIED   3 Hour – Cruise&Sail (11 AM) on May 24, 2025
Wes was super cool, responsible but allowed the kids to have fun.
Micah H. recommends Tradewinds Charters – My Sunshine
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Micah H. recommends Tradewinds Charters – My Sunshine
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Debra S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Memories

VERIFIED   3 Hour–Cruise&Snorkel (11AM) on July 12, 2025
Excellent trip, courteous crew
Debra S. recommends Tradewinds Charters – Sea Scape
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