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%
Sort by:
Featured  
Showing:
5 of 22 reviews
Thea A.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Excellent!

VERIFIED   3 Hour – Cruise&Sail (11 AM) on October 13, 2025
Great time, laid back atmosphere with a fun captain!
Thea A. recommends Tradewinds Charters – My Sunshine
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Thea A. recommends Tradewinds Charters – My Sunshine
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Sean H.
Excellent
4.3 / 5
Experience:
Good
3.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Blown away

VERIFIED   3 Hour – Cruise&Sail (2 PM) on March 25, 2026
sails up no motor noise, beautiful water, beautiful sunset, and a spectacular captin.
Sean H. recommends Tradewinds Charters – My Sunshine
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Sean H. recommends Tradewinds Charters – My Sunshine
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Shelley C.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Boating with Ken

VERIFIED   2 Hour – Sunset Cruise on February 22, 2026
Shelley C. recommends Tradewinds Charters – My Sunshine
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  Ken Middleton Captain replied
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Stanislav K.
Excellent
4.7 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Very good
4.0 / 5
Overall

Boating with Ken

VERIFIED   3 Hour–Cruise&Snorkel (1-6 people) on December 26, 2025
Stanislav K. recommends Tradewinds Charters – Sea Scape
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Stanislav K. recommends Tradewinds Charters – Sea Scape
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Eric E.
Excellent
4.7 / 5
Experience:
Very good
4.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Boating with Ken

VERIFIED   3 Hour – Cruise&Sail (11 AM) on October 15, 2025
Eric E. recommends Tradewinds Charters – My Sunshine
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Eric E. recommends Tradewinds Charters – My Sunshine
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