Ten days across two islands that feel like two different countries, the soft, green sweetness of Maui and the wild, lava-black drama of Hawai‘i Island. Built around the two Four Seasons properties that have quietly defined family luxury in the Pacific, with the kind of private guides and outfitters that turn a beautiful beach vacation into a story your children will tell for the rest of their lives.
Private transfer from Kahului Airport south to Four Seasons Resort Maui at Wailea, the gold-standard family resort on the island, with no resort fees, the Kids For All Seasons program (free, full-day, ages 5+), and ocean-front Plunge Pool Suites that earn the price. After a rest, an unhurried first evening at the Serenity Pool, dinner at Ferraro’s right on the sand, the kids barefoot in the warm grass.
Built on purpose with nothing on the schedule. Morning at the resort beach (the gentlest surf on the island), a private shave ice delivery to the pool at 11 AM, lunch at the open-air Duo. Optional afternoon stand-up paddleboard or outrigger canoe lesson from the beach hut, taught with so much warmth that even nervous adults try it. Sunset cocktails at the Lobby Lounge, a casual dinner at the resort’s poolside restaurant, an early bedtime for everyone.
A private guide and Land Cruiser collects you at 7 AM, early enough to have the waterfalls to yourselves. The Road to Hāna in a rental car is famously stressful; with our guide it becomes one of the great days. Stops at the Twin Falls, the bamboo forest, the black sand beach at Waiʻānapanapa, lunch at a roadside huli-huli chicken stand the locals love. Quiet return through the back side of Haleakalā by mid-afternoon, in time for the resort pool and an early dinner.
Morning private catamaran out to the Molokini crater, a half-submerged volcanic ring with some of the clearest water in the islands. Snorkel gear and a marine biologist on board for the kids, lunch on the boat as you sail home. Afternoon at the resort for naps and the pool. Evening at the Old Lahaina Lūʻau (or the Feast at Lele as a more intimate alternative), the authentic Hawaiian lūʻau, with imu pork pulled from the ground, hula taught with reverence, and a sunset that feels staged.
For families with older children: a 3:30 AM private drive up to the summit of Haleakalā to watch the sunrise above the clouds at 10,000 feet, one of the singular experiences in Hawaii, and worth the alarm. Back to the resort by mid-morning for breakfast and a nap. Afternoon private transfer to Kahului, short inter-island flight (about 45 minutes) to Kona, and a driver to Four Seasons Resort Hualalai on the Kohala Coast. Quiet welcome dinner at ULU Ocean Grill, on the sand.
Hualalai is built on a 5,000-year-old lava flow, and the resort’s reef pool is the only one of its kind in the world, a saltwater snorkel pool stocked with 4,000 tropical fish. Morning swimming with the kids there, a private surf lesson at the resort beach (the gentlest break in Kohala), lunch at the Beach Tree. Afternoon at the Kids for All Ages cultural center, where children can string lei, pound poi, and learn ʻōlelo Hawaiʻi from a kupuna (elder). Sunset on the lawn with shave ice.
Quieter morning at the resort, paddleboard, beach, the spectacular spa for the adults. Late afternoon picnic at Hāpuna Beach (often ranked among the best in the world). After dinner, a private boat to a known feeding site for the famous Big Island manta ray night snorkel, the boat shines lights into the water, and the giant rays (utterly harmless) come up to feed within arm’s reach. It is, almost without exception, the experience families talk about for the rest of the trip.
Long day, fully worth it. A private driver/naturalist takes you across the island to Hawaiʻi Volcanoes National Park, about two and a half hours each way through five distinct climate zones. The Kīlauea caldera, the lava tubes, the still-steaming vents, a walk across an old lava field. Lunch at the historic Volcano House overlooking the crater. Stop on the way home at Punaluʻu Black Sand Beach to look for sea turtles. Late return, in-room dinner.
On purpose. Morning private outrigger canoe paddle from the resort beach with a Hawaiian cultural practitioner, the kids will paddle harder than they thought they could. Lunch at the Hualalai Trading Company on the way back. Afternoon spa for the grown-ups, Kids for All Ages for the children, an early aloha-themed dinner on the lawn under the torches. A final sunset walk along the beach, looking for green flashes and turtles coming in for the night.
A leisurely breakfast and a late checkout. Private transfer to Kona International for afternoon flights home, or an extension to Kauai’s Grand Hyatt or the newly refreshed Mauna Kea for one more island.
