Tradewind Charters

Company Bio

Tradewind Charters specializes in private day and evening cruises from Oahu. Unlike other charter companies, we operate a number of vessels that can accommodate 2–75 guests safely and comfortably. Whether you’re planning a wedding, group fishing trip or a romantic sunset sail dinner, we provide the very best in private boat charters for clients from all over the world.

Captain Ken Middleton started Tradewind Charters 30 years ago after sailing to Hawaii from the West Coast. As a self-proclaimed “sailing refugee from the mainland,” he emboldens others to seize the day. He often quotes Mark Twain: “Years from now, you will be more disappointed by the things you didn’t do than by the ones you did, so throw off the bowline, sail away from the safe harbor, catch the tradewinds in your sail, and explore, dream, discover!”

Contact Information

Phone: (808) 227-4956
(808) 829-4899


Slip Information

Located at SLIP B6 B8
Vessel Name: My Sunshine/Aloha Kai

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