Featured Adventures

From $495

Ideal for the romantic couple who’s up at the crack of dawn during their Hawaiian vacation due to time zone changes. Witness the brilliant colors of a sunrise at sea from the deck of the…

Aloha to Tradewind Charters

Tradewind Charters Hawaii offers visitors and Kama’ainas private sailing cruises, fishing charters, sunset dinner sails, snorkeling tours, whale watching and dolphins swims, scenic sightseeing tours, weddings at sea, sea burial services, and much more. Whether you are looking to relax for an afternoon or a whole week, host a wedding and reception at sea, entertain family, friends, and business associates for a luncheon cruise, or savor a romantic sunset dinner sail, we do it all for you.

30 years if exceptional charter service

Meet Captain Ken

Capt. Ken at the helm. Over 25 years ago, I sailed over from the West Coast and started up Tradewind Charters to provide the very best in private boat charters for clients from all over the world. Our islands’ perfect weather is ideal for sailing and living in comfort, and coupled with an unsurpassed beauty and allure, incredible marine life year-round, and neighbors full of ALOHA, it truly is Paradise. Come sail with us and let us show you the reasons why we call these islands home.

Capt Ken

Raving Reviews

"Enjoyed Our Sailing Trip"

"A group of four of us took a morning sailing cruise out past the shores of Waikiki. Captain Nate was a great source of information and shared some fantastic recommendations of things to see/do. He was very personable and informative and made our trip very enjoyable."

– James C.
"Sunset Cruise"

"This was an amazing way to end our vacation in Hawaii. Our family sailed for two hours and enjoyed the sunset while eating and drinking. Best of all it was just us! Our own private cruise. Paul was an incredible captain and host who took care of all of our needs. We just sat back and enjoyed the ride."

– Christine B.
"My Sunshine sail trip"

"My family thoroughly enjoyed a three-hour sail trip on "My Sunshine." Captain Paul was amazing, as was the boat trip. Beautiful say on Waikiki swimming, sailing and enjoying the sun. Perfect cruise!!!!"

– Kent K.
Wonderful Experience

"I had a WONDERFUL experience. Captain Ken was incredibly responsive and easy to coordinate with. He and his crew made sure that we had an enjoyable and safe time out on the water. The boat was incredibly clean, and well-equipped with everything you would need - snorkels, bathrooms, and a full bar! Can't wait to sail again with Tradewind Charters."

– Chris B.