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.
21
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
(11 reviews)
Honolulu
 Instant Confirmation
trips from US $695

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 21 reviews
See details
Boat
Excellent
4.7 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (6)
Dolphins!
Memorial ash release for 3 family members
Memorial ash release for 3 family members
+3
Customer rating
17
2
1
0
0
Customers claimed
Good experience
86%
Friendly captain
100%
Recommend this charter
90%
Appropriate for children
100%
Satisfied with the boat
90%
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Featured  
Showing:
5 of 21 reviews
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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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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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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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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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 (1-12 people) 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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