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Established in Hawaii over 25 years ago, Tradewind Charters is a leading provider of private sailing cruises on Oahu. Choose from a selection of both sailing & motor vessels. All vessels are based on Oahu with some of their overnight/interisland vessels available for outerisland pick-up/drop-offs. Their sailing fleet includes a 12-passenger sailing sloop, a 49-passenger sailing catamaran, a 50-foot Gulfstar ketch, and their newest addition - a yacht that can accommodate up to 80 guests. Their motor yacht fleet ranges from a 43-foot Mediterranean Sports Fisherman to a classic 65-foot Stephens motor yacht. So whether you are planning a wedding, private whale watching sail, or a corporate party, let Tradewind Charters realize your sailing adventure.