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
Lia R.
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 (11 AM) on September 8, 2025
Mikey was a great captain! Extremely knowledgeable and great fun. Definitely highly recommend!
Lia R. recommends Tradewinds Charters – My Sunshine
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Lia R. recommends Tradewinds Charters – My Sunshine
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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   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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Thea A.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Excellent!

VERIFIED   3 Hour – Cruise&Snorkel (11 AM) on October 13, 2025
Great time, laid back atmosphere with a fun captain!
Thea A. recommends Tradewinds Charters – My Sunshine
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Thea A. recommends Tradewinds Charters – My Sunshine
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Sean H.
Excellent
4.3 / 5
Experience:
Good
3.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Blown away

VERIFIED   3 Hour – Cruise&Snorkel (2 PM) on March 25, 2026
sails up no motor noise, beautiful water, beautiful sunset, and a spectacular captin.
Sean H. recommends Tradewinds Charters – My Sunshine
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Sean 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 (1-12 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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