Boat-Tour

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.

Boat tours along the leeward coast offer some of the best wild dolphin and sea turtle encounters in Hawaii. Spinner dolphins frequently swim alongside and under the boats in pods of dozens. Several operators also stop at snorkeling reefs where sea turtles are almost guaranteed. The leeward coast is drier and calmer than other parts of Oahu making for comfortable boat conditions. Seeing dolphins leap and spin in the wild is one of those magical moments that stays with kids forever. Choose operators who follow responsible wildlife viewing guidelines.

Maui is one of the best whale watching destinations in the world. Humpback whales migrate here every winter and the waters between Maui, Lanai, and Molokai are a prime calving ground. Boat tours regularly encounter breaching, tail slapping, and mother-calf pairs at close range. Kids are absolutely spellbound by these massive creatures. The Pacific Whale Foundation and other operators run multiple daily departures. Even from shore, whales are often visible from December through April. The experience is awe-inspiring at any age.

A boat trip to a partially submerged volcanic crater 3 miles offshore with some of the clearest water and best snorkeling in all of Hawaii. Visibility often exceeds 150 feet and the protected interior of the crescent-shaped crater is calm and teeming with tropical fish. Kids are amazed by the underwater visibility and the sheer number and variety of fish. Most tours include snorkel gear, breakfast, and lunch on board. Morning departures offer the calmest conditions. Sea turtles and sometimes reef sharks are spotted in the deeper areas.

A boat tour along the most dramatic coastline in Hawaii with 4,000-foot sea cliffs, cascading waterfalls, sea caves, and hidden valleys. The Na Pali Coast is inaccessible by car so seeing it by boat is the most family-friendly option. Most tours include snorkeling at a reef along the coast and the chance to enter sea caves. Spinner dolphins and sea turtles are frequently spotted. Kids are awestruck by the sheer scale of the cliffs and waterfalls. Choose a catamaran for a smoother ride. Summer has the calmest conditions.