Tradewind Charters

Tradewind Charters has operated sailing and power charters out of Kewalo Basin harbor in Honolulu since 1985, when founder Captain Ken sailed his own sloop from Seattle to Hawaii to establish the company. Four decades later, the fleet includes three named vessels — the 43-foot sailing monohull My Sunshine (up to 6 guests), the 40-foot sailing catamaran Sea Scape (up to 12 guests), and the 50-foot power catamaran Aloha Kai (up to 49 guests) — along with a 65-foot sailing catamaran that accommodates up to 80 guests. Private charters cover a wide range of occasions: daytime snorkel cruises, sunset and moonlight sails, Friday fireworks cruises, reef fishing excursions, whale watching, and a sunrise mimosa sail. The company hosts weddings at sea on any vessel in the fleet, with a USCG-licensed captain available to perform the ceremony. Customizable catering, beverage packages, and round-trip limousine service round out the event options.