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
Chad C.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great crew, great trip

VERIFIED   3 Hour–Cruise&Snorkel (2PM) on October 2, 2025
Mikey and Luke took great care of our group of 11. They were friendly engaging and made sure we had a great time.
Chad C. recommends Tradewinds Charters – Sea Scape
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Chad C. recommends Tradewinds Charters – Sea Scape
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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&Sail (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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Lia R.
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&Sail (11 AM) on September 8, 2025
Mikey was a great captain! Extremely knowledgeable and great fun. Definitely highly recommend!
Lia R. recommends Tradewinds Charters – My Sunshine
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Lia R. recommends Tradewinds Charters – My Sunshine
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Amber W.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Mikey and Gareg are great!

VERIFIED   3 Hour–Cruise&Snorkel (1-6 people) on January 1, 2026
We had the best times. Till next year! “Ahoooy”!
Amber W. recommends Tradewinds Charters – Sea Scape
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Amber W. recommends Tradewinds Charters – Sea Scape
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Ryan R.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Good family time

VERIFIED   3 Hour–Cruise&Snorkel (1-6 people) on December 20, 2025
We had a good time on our trip as a family of 3
Ryan R. recommends Tradewinds Charters – Sea Scape
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Ryan R. recommends Tradewinds Charters – Sea Scape
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