Sailing in Kailua, HI

Customize your private Waikiki charter for groups up to 40

Private 6-hour sail to Waimea Bay for up to 6 people

Relax on the water with Waikiki and Diamond Head views

Private late-afternoon sail with sunset views of Honolulu and Oahu’s shores

A weekday sail with Hawaiian cultural activities and refreshments

Watch Waikiki's Friday fireworks from a 55-foot catamaran

Sail past Waikiki and Diamond Head with a full bar onboard

Sail off Waikiki with ocean views, splashy fun, and drinks available onboard

Private morning sailing with mimosas and open-water views

Toast the evening with coastal views and a full open bar

Sail Friday night and watch Honolulu fireworks from the water

Learn foundational sailing skills with professional captains in Hawaii

Golden-hour views of Waikiki and Diamond Head

Sail the North Shore with a naturalist and seasonal whale listening

Friday fireworks sail with front-row views from the water

Sail into Friday night for Waikīkī fireworks views from the water

Sail into Hawaiian culture with music, activities, and refreshments

Swim, relax, and sail past Waikiki and Diamond Head

Sail Oʻahu’s coast before an evening of island dining and culture

Open-bar Mai Tais and coastal views as the sun sets

Take the Helm With Private Sailing Instruction

Celebrate on a private sail along Oʻahu’s coast with views of Diamond Head

Explore Hawaiian culture and ocean landscapes on a family-friendly morning sail

Afternoon catamaran sail with included drinks and Waikiki views