Escape on a Private Charter!

Tradewind 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 2-150 guests.

As Mark Twain opined 100+ years ago; "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."

Call Capt Ken today at 1-800-829-4899 to schedule your private cruise in Paradise!!  

Captain Ken Middleton

Capt Ken at the helm. 25 years ago I sailed over from the West Coast and started up Tradewind Charters to provide the best in private sailing cruises 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 & muggy, 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 a little aloha into your lives as well, come sail with us and let us show you the reasons why we call these islands home.