Day-Sail

A 47-foot gaff-rigged Hudson River ferry sloop commissioned by Pete Seeger in 1978, crewed entirely by volunteers, running free evening sails on the Hudson out of the park beside Beacon’s Metro-North station. There is never a charge to sail aboard the Woody Guthrie, though donations are invited, and no sailing experience is needed. A different volunteer captain takes her out each weeknight, and reservations are made by phone. The club also puts on three free festivals a year with music and kids activities on the same waterfront.

Kona’s longest-running sailing catamaran, a custom 36-foot boat that is 22 feet across, with a wide forward trampoline kids end up sprawled on for most of the trip. The sail runs up the Kona coast to Pawai Bay for snorkeling and a light lunch, then back under sail. Capacity is 24 but they usually carry fewer, so it does not feel like a party boat. The minimum age is 7 on the snorkel, manta and whale trips; the sunset cruise is adults only.

Waikiki’s longest-running catamaran, sailing since 1977 and launching straight off the sand in front of Duke’s, between the Royal Hawaiian and the Outrigger Waikiki. The day sail is a single hour out toward Diamond Head and back under sail, which is about the right length for small children and costs less than most Hawaii activities. There is no minimum age and boarding is a walk down the beach rather than a harbor check-in, so it works as a spur-of-the-moment outing on a beach day. This is the cheapest way to get a family onto a sailboat in Hawaii.

A 44-foot catamaran that launches off the sand behind the Sheraton Waikiki and sails the water directly in front of Waikiki with Diamond Head off the stern. The operator’s own description is that the wind and waves are the engine, and it has a reputation among Waikiki boats for actually hoisting sail. The 11am and 1pm Tradewind sails are the family slot and the cheapest; the later afternoon and sunset departures are built around an open bar and cost more. Children under 3 sail free and there is a child rate through age 12.

Performance sailing catamarans out of Maalaea Harbor that make a point of actually sailing rather than motoring, which is unusual among Maui day boats. Trips run to Molokini, the Lanai coast, or Coral Gardens for snorkeling, and the shorter West Maui and Coral Gardens sails are the easiest sell for younger kids. The boats carry between 25 and 49 guests, small enough that children can sit up on the trampolines between the hulls and watch the water go by underneath. Sail Maui also departs from Lahaina Harbor during daylight hours, though sunset departures run from Maalaea only while Lahaina Harbor lighting is still being restored.

A 1926 John Alden designed wooden schooner, the same boat used in the 1956 film High Society, running two-hour public sails off the southern tip of Seneca Lake. She carries up to 22 passengers, with cushioned seating for sixteen on the cabin top if the weather turns. Water and juices are included. Soft-soled shoes are required on deck, which is worth knowing before you get to the pier with a kid in sandals. Up to four departures a day makes this easy to slot into a Watkins Glen trip alongside the gorge.

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.