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.
22
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
(9 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 22 reviews
See details
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
Brook F.
Very good
3.3 / 5
Experience:
Good
3.0 / 5
Boat
Very good
4.0 / 5
Crew
Good
3.0 / 5
Overall

Boating with Ken

VERIFIED   3 Hour – Cruise&Sail (11 AM) on April 7, 2026
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful
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&Sail (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
Mark review as helpful
You found this review helpful
Derek K. recommends Tradewinds Charters – My Sunshine
Mark review as helpful
You found this review helpful
Read more
  • Settings