Sailing

A family-run Maui sailing outfit since 1973, running big catamarans to Honolua Bay and Olowalu Reef with breakfast and a hot lunch cooked on board. The crew size snorkel gear down to about age 4 and put flotation vests on the little ones, and there is in-water instruction for anyone who has never snorkeled before. The boats motor out and then genuinely raise sail for the run home, which is the part kids remember. Trilogy resumed departures from Lahaina Harbor in March 2026, its first since the 2023 fire, and also sails from Kaanapali Beach and Maalaea Harbor. Note that the dinner and sunset sails are adults only, so the daytime snorkel trips are the family option.

A nonprofit community sailing center on a small, sheltered lake where the boats stay in sight of the dock, which makes it an unusually low-anxiety place for a first sail. Both residents and non-residents can buy an annual pass, which covers unlimited sailboat, kayak and paddleboard use during operating hours, and family passes cover up to four people. Five-day camps split into a morning block for ages 8 to 12 and an afternoon block for teenagers, taught by US Sailing certified instructors covering how wind moves a boat, boat parts, wind strength and direction, flotation and sailing weather. Scenic sails take children from age 5.