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.
14
Reviews
Verified

My Listings

Tradewinds Charters – Aloha Kai

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

Tradewinds Charters – Sea Scape

Excellent
4.9 / 5
(7 reviews)
Honolulu
 Last booking: 1 day ago
 Instant Confirmation
trips from US $995

Tradewinds Charters – My Sunshine

Excellent
4.8 / 5
(6 reviews)
Honolulu
 Last booking: 5 days ago
 Instant Confirmation
trips from US $695

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 14 reviews
See details
Boat
Excellent
4.8 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (5)
Memorial ash release for 3 family members
Memorial ash release for 3 family members
Memorial ash release for 3 family members
+2
Customer rating
12
1
0
0
0
Customers claimed
Good experience
100%
Friendly captain
100%
Recommend this charter
93%
Appropriate for children
100%
Satisfied with the boat
100%
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Featured  
Showing:
5 of 14 reviews
Beckee J.

The captain canceled

VERIFIED   NEW  January 1, 2026
The charter operator canceled on trip date. This is an automated posting.
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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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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   NEW  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   NEW  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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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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