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.

My Listings

Excellent
5.0 / 5
(2 reviews)
Honolulu
 Instant Confirmation
trips from US $1,500
Excellent
5.0 / 5
(9 reviews)
Honolulu
 Instant Confirmation
trips from US $1,495
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
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
Charmaine F. R.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Amazing experience! Highly recommended

VERIFIED   Charmaine private charter on July 2, 2026
We came to Hawaii to celebrate both of my nephews graduating, and this private charter was my gift to them. We were originally...
Charmaine F. R. recommends Tradewinds Charters โ€“ Sea Scape
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Craig E.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Very knowledgeable crew!

VERIFIED   3 Hourโ€“Cruise&Snorkel (11AM) on May 12, 2026
The crew was a big help in walking us through the process for spreading my wifeโ€™s ashes as she wished. It made a difficult...
Craig E. recommends Tradewinds Charters โ€“ Sea Scape
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Craig E. recommends Tradewinds Charters โ€“ Sea Scape
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Sydney S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Such a great crew and experience!

VERIFIED   2 Hr Trip โ€“ Sunset Cruise on February 13, 2026
The captain and crew were so kind, organized, and welcoming. We had a full boat of 20-30 somethings and they got us all checked...
Sydney S. recommends Tradewinds Charters โ€“ Aloha Kai
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  Ken Middleton Captain replied

Velma M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Amazing trip!!

VERIFIED   3 Hour โ€“ Cruise&Sail (11 AM) on May 25, 2026
csptain was great enjoy the adveture we had ย 
Velma M. recommends Tradewinds Charters โ€“ My Sunshine
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Velma M. recommends Tradewinds Charters โ€“ 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 โ€“ Cruise&Sail (2 PM) on December 4, 2025
Wes was great, he found the wildlife we were looking for and was a gracious host in general.ย  Highly recommend this tour.
Kevin M. recommends Tradewinds Charters โ€“ My Sunshine
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Kevin M. recommends Tradewinds Charters โ€“ My Sunshine
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