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%
Sort by:
Featured  
Showing:
5 of 21 reviews
Derek K.
Excellent
4.3 / 5
Experience:
Very good
4.0 / 5
Boat
Very good
4.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great day for snorkeling

VERIFIED   3 Hour – Cruise&Snorkel (11 AM) on July 22, 2025
Had an exceptional time getting to the reef and our captain deployed tricks of the trade to draw schools of fish to our spot...
Derek K. recommends Tradewinds Charters – My Sunshine
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Derek K. recommends Tradewinds Charters – My Sunshine
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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&Snorkel (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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Carlos W.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Ash spreading ceremony

VERIFIED   2 Hour–Sunset Cruise (1-12 people) on June 22, 2025
Excellent experience. Crew was extremely respectful. Went out of their way to show us some spotted eagle rays that swam along...
Carlos W. recommends Tradewinds Charters – Sea Scape
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Micah H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Yessah!

VERIFIED   3 Hour – Cruise&Snorkel (11 AM) on May 24, 2025
Wes was super cool, responsible but allowed the kids to have fun.
Micah H. recommends Tradewinds Charters – My Sunshine
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Micah H. recommends Tradewinds Charters – My Sunshine
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