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Escape on a Private Charter!

Exceptional Charter Services for 25yrsTradewind Charters Hawaii offers visitors and kamaainas 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 to relax and cruise for an afternoon or a whole week, host a wedding and reception at sea, entertain family, friends and business associates for a fun luncheon cruise, or romantic sunset dinner sail we do it all for you. Beautiful views, beautiful experiences and beautiful memories for 2-75 guests.


Aloha & Welcome to Tradewind Charters

Capt. Ken Middleton



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. As a sailing refugee from the mainland, I can empathize with our visitors that hail from somewhere that's always too hot, too cold or the wind doesn't blow. 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. I love meeting people from all over the world as they enjoy our island hospitality, culture, sights, history and uniqueness. I hope that my staff and I can bring Aloha into your lives as well. Come sail with us and let us show you the reasons why we call these islands home. A wise man's words from the 19th century still ring true...

"Years from now you will be more disappointed by the things you didn't do than by the ones you did do. So throw off the bow lines. Sail away from the safe harbor. Catch the tradewinds in your sails. Explore. Dream. Discover."~ Mark Twain