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.
19
Reviews

My Listings

Tradewinds Charters – Aloha Kai

Excellent
5.0 / 5
(2 reviews)
Honolulu
 Last booking: 2 days ago
 Instant Confirmation
trips from US $1,500

Tradewinds Charters – Sea Scape

Excellent
4.9 / 5
(7 reviews)
Honolulu
 Instant Confirmation
trips from US $1,495

Tradewinds Charters – My Sunshine

Excellent
4.7 / 5
(10 reviews)
Honolulu
 Instant Confirmation
trips from US $695

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 19 reviews
See details
Boat
Excellent
4.7 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (6)
Dolphins!
Memorial ash release for 3 family members
Memorial ash release for 3 family members
+3
Customer rating
15
2
1
0
0
Customers claimed
Good experience
83%
Friendly captain
100%
Recommend this charter
89%
Appropriate for children
100%
Satisfied with the boat
89%
Sort by:
Featured  
Showing:
5 of 19 reviews
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
Mark review as helpful
You found this review helpful
Ryan R. recommends Tradewinds Charters – Sea Scape
Mark review as helpful
You found this review helpful
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
Mark review as helpful
You found this review helpful
  Ken Middleton Captain replied
Read more
Beckee J.

The captain canceled

VERIFIED   January 1, 2026
The charter operator canceled on trip date. This is an automated posting.
Mark review as helpful
You found this review helpful
Mark review as helpful
You found this review helpful
Shelley C.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Boating with Ken

VERIFIED   2 Hour – Sunset Cruise on February 22, 2026
Shelley C. recommends Tradewinds Charters – My Sunshine
Mark review as helpful
You found this review helpful
  Ken Middleton Captain replied
Read more
Chad C.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great crew, great trip

VERIFIED   3 Hour–Cruise&Snorkel (1-12 people) on October 2, 2025
Mikey and Luke took great care of our group of 11. They were friendly engaging and made sure we had a great time.
Chad C. recommends Tradewinds Charters – Sea Scape
Mark review as helpful
You found this review helpful
Chad C. recommends Tradewinds Charters – Sea Scape
Mark review as helpful
You found this review helpful
  • Settings