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.
A genuine Hawaiian sailing outrigger canoe launched straight off Polo Beach in Wailea, with groups capped at eight people. The family helps push the canoe out through the shore break, which kids love, and then the sail goes up for a run along the Wailea coast. The crew teach traditional navigation and paddling along the way, and there is a snorkel stop where green sea turtles are common. It is the smallest and most hands-on sailing trip on Maui, and the closest thing to sailing the way Hawaiians actually did it.
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 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.
An oceanfront campground in the Kipahulu district of Haleakala National Park, on a grassy bluff above the surf at the end of the Road to Hana. Camping here turns the notorious Hana drive from a rushed day trip into two relaxed days, and it puts the Pipiwai Trail and the Oheo Gulch pools a short walk from your tent, hours before the tour vans arrive. Facilities are minimal: pit toilets, picnic tables, grills, and no potable water at all. Bring every drop you plan to drink.
A protected natural area on Maui south shore with excellent snorkeling in calm, clear water over lava rock reef. The reserve sits on the last lava flow on Maui and the underwater landscape of lava formations covered in coral is fascinating. Fish, turtles, and eels are common. The entry is over lava rock so water shoes are essential. There are no facilities and no lifeguards so this is for families comfortable with independent ocean swimming. The marine life here is abundant because the area is well protected.
A challenging but rewarding 3.5-mile round trip hike down (and back up) a steep trail to the Captain Cook Monument at the edge of Kealakekua Bay. The payoff is some of the best shore-access snorkeling in Hawaii in a marine sanctuary with spinner dolphins, tropical fish, and pristine coral. The hike down through dry scrubland drops about 1,400 feet. The climb back up in the heat is the hard part so bring extra water. For families with fit older kids who can handle the physical demands, the snorkeling at the bottom is genuinely world-class.
A unique snorkeling spot where warm water discharged from a nearby power plant attracts an incredible diversity of marine life. Spinner dolphins, sea turtles, eagle rays, and dense schools of fish are regularly seen in the warm outflow channel. The visibility is good and the marine life density is higher than almost anywhere else on Oahu. The entry is over rocks and there are no lifeguards so this is best for experienced swimmer families. When conditions are calm, the snorkeling is genuinely world-class and free.
A stunning tropical garden on a dramatic ocean bluff north of Hilo with trails winding through over 2000 species of tropical plants and flowers. The garden descends into Onomea Bay with viewpoints of waterfalls, the ocean, and towering palms. Kids enjoy the boardwalk trail that passes a waterfall and crosses bridges over streams. The variety of exotic flowers, palms, and tropical plants is incredible. This was a filming location for Jurassic Park and you can see why. The beauty is overwhelming and photographs here look like they were taken in a fantasy world.
A gorgeous 3-mile stretch of golden sand on Maui west side that is consistently rated among the best beaches in the world. The water is calm and clear making it excellent for swimming and snorkeling. Black Rock at the north end is one of the best shore snorkeling spots on Maui with sea turtles and tropical fish. Every evening at sunset a cliff diving ceremony from Black Rock draws a crowd. The beachfront walk connects hotels, restaurants, and shops. Snorkel gear can be rented at multiple spots along the beach.
A stunning 3.5-mile coastal boardwalk and trail connecting several beautiful bays along Maui west shore. The trail is mostly flat and paved with sections of boardwalk over lava rock. Kids can spot sea turtles, whales in winter, and tide pool creatures along the way. Several beaches along the route offer swimming stops. Kapalua Bay at one end and DT Fleming Beach at the other are both excellent for families. This is one of the most scenic easy walks in all of Hawaii.
A paved multi-use path along the east coast of Kauai stretching about 4 miles from Lydgate Beach to Kapaa town and beyond. The path hugs the coastline with ocean views the entire way and passes beaches, parks, and the Kapaa town shops and restaurants. Bike rentals are available near the path. Kids love cruising along the oceanfront and stopping at beaches along the way. The path is flat and smooth, perfect for family biking. Whale watching from the path is excellent in winter. This is the most scenic bike ride in all of Hawaii.
A marine sanctuary with crystal-clear water, incredible coral reefs, and abundant marine life that offers some of the best kayaking and snorkeling on the Big Island. Guided kayak tours cross the bay to the Captain Cook Monument where spinner dolphins are regularly seen and the snorkeling is world-class. The reef is teeming with tropical fish, eels, and sea turtles. The water clarity is exceptional. Kids who are comfortable swimming and kayaking will have one of the most memorable ocean experiences of their lives.
The most reliable spot on Oahu to see Hawaiian green sea turtles basking on the sand or swimming in the shallow water. Volunteers are often present to educate visitors and ensure people maintain the required 10-foot distance from the turtles. Kids are thrilled to see these gentle creatures up close on the sand. The beach itself is rocky and not ideal for swimming but the turtle viewing alone makes it worth the stop. Located on the scenic North Shore drive between Haleiwa and the Dole Plantation. The best viewing is usually in the afternoon.
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.
Snorkel with giant manta rays at night in one of the most unforgettable wildlife encounters in Hawaii. Operators set up surfboards with lights that attract plankton, which in turn attract manta rays with wingspans up to 12 feet that glide inches below you as they feed. Kids hold onto the lit surfboard and float face-down watching the graceful mantas do barrel rolls in the light. It sounds scary but the rays have no teeth or stingers and the experience is peaceful and awe-inspiring. This is a bucket-list Hawaii activity.
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.