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

VIEW SITE

Slip Information

Located at SLIP A-20
VIEW SLIP MAP
Vessel Name: My Sunshine

Not What You're Looking For?
Take a Look at These Other Adventures!

Hawaii Nautical

One of Hawaii’s largest ocean activity providers, we provide unbeatable guarantees. If you don’t see dolphins and sea turtles on our tours, come again FREE....

ONLINE BOOKING

Makani Catamaran

Unlike any other charter boat on Oahu, Makani offers the exhilaration of Grand Prix speed sailing with the extravagance of a five-star hotel....

ONLINE BOOKING