Best results for Sailing in Haleiwa, HI

Private sailing charter on Oahu’s North Shore for up to 6 people

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

Sail the North Shore with a naturalist and seasonal whale listening

Unwind on the water as the sun sets over the horizon

Private 2-hour Honolulu sunset sail with voyaging dinner and cultural activities

A weekday sail with Hawaiian cultural activities and refreshments

Sail into Hawaiian culture with music, activities, and refreshments

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

Sail O'ahu's Kona coast with Hawaiian stories, activities, and deckside relaxation

Sunset sailing with cocktails, appetizers, and shoreline wildlife viewing

Set your own agenda on a private Waikiki sail for up to 6 guests

Sail the Wai Kai Lagoon with captain-led lessons or approved self-operation

Sail into sunset views with a relaxed evening on the water

Sail past Waikiki and Diamond Head with a full bar onboard

See wild dolphins, snorkel with turtles, and enjoy lunch on a 3-hour West Oahu sail

Sail Waikīkī at sunset with drinks and light bites included

Unwind on a West O‘ahu sunset cruise with panoramic views, drinks, and light bites included

Sail at sunset for front-row views of Waikiki’s Friday fireworks, with drinks and a bento included

Relax along Oʻahu’s south shore with Waikiki views, Diamond Head, snacks, and drinks

Toast the evening with coastal views and a full open bar

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

Bring your own drinks for a sunset sail along Waikiki’s coast

Private sailing with Waikiki views, swimming, and snorkeling options

Learn foundational sailing skills with professional captains in Hawaii