Private sailing from Honolulu

Tradewind Charters

Tradewind Charters runs private Oahu boat charters from Honolulu, including sailing cruises, snorkeling, sunset sails, fishing, whale watching and events at sea.

Tradewind Charters is located at Kewalo Basin Harbor, only a few minutes west of Waikiki, and offers private sails that leave the crowds behind the moment your deck shoes clear the pier. You step aboard a classic 43-foot sailing yacht—bright teak trim, shaded cockpit, cushioned bow lounge—and watch the skipper ease past the harbor jetty while crew coil lines and raise the main. With the city skyline shrinking astern, Diamond Head fills the horizon and steady trade winds carry you toward blue-water calm.

Day sails cover two to four hours, gliding south along Waikiki's reef where spinner dolphins often leap beside the hull and green sea turtles surface for lazy breaths. Snorkel time is optional but easy; masks, fins and foam noodles come included, and a stainless swim ladder drops you into water that often clears 60 feet. Back on deck, iced fruit, deli wraps and tropical soft drinks land on the cockpit table while island music drifts from a Bluetooth speaker.

Sunset cruises swap snorkels for camera lenses. The captain times a gentle reach so the sails silhouette against golden light, then idles a mile offshore while you toast the day with chilled prosecco and pupu platters of teriyaki chicken skewers, fresh pineapple and Maui onion chips. On Friday nights, the yacht hovers off Waikiki to catch the Hilton fireworks bursting over the lagoon in full, unobstructed color.

Custom charters let you steer the itinerary—full-day sails to swim with turtles off Turtle Canyon, ash-scattering ceremonies held in peaceful lee waters, or inter-island passages that trace historical trade routes. The yacht carries inflatable SUP boards, fishing tackle and a well-stocked galley that can upgrade from sandwich trays to chef-prepared lobster with advance notice. USCG-licensed crew hold CPR and first-aid certification, and redundant navigation gear keeps safety second nature while you focus on the view.

All trips include gear, reef-safe sunscreen, bottled water and soft drinks; alcoholic beverages are welcome on a BYOB basis, and ice chests await on board. Parking is available in the marina lot, and charters depart rain or shine—the cockpit's canvas bimini and below-deck salon keep the experience comfortable if a shower drifts by.

Ready to trade hotel balconies for billowing canvas and horizon-wide views? Reserve your private sail with Tradewind Charters, then browse our catalog of Oahu tours and activities to fill the rest of your island days once the sails are furled and the deck lines are snug.