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.
16
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
 2 bookings in the past week.
 Instant Confirmation
trips from US $995

Tradewinds Charters – My Sunshine

Excellent
4.9 / 5
(8 reviews)
Honolulu
 Last booking: 2 days ago
 Instant Confirmation
trips from US $695

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 16 reviews
See details
Boat
Excellent
4.9 / 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
14
1
0
0
0
Customers claimed
Good experience
100%
Friendly captain
100%
Recommend this charter
94%
Appropriate for children
100%
Satisfied with the boat
100%
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Showing:
5 of 16 reviews
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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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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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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Debra S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Memories

VERIFIED   3 Hour–Cruise&Snorkel (7-12 people) on July 12, 2025
Excellent trip, courteous crew
Debra S. recommends Tradewinds Charters – Sea Scape
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  Ken Middleton Captain replied
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