Hawaiian Discovery

Four Islands. Exceptional Resorts. Private Flights

Twelve nights · Thirteen days

Maui → Lānaʻi → Kauaʻi → Island of Hawaiʻi

Discover four Hawaiian islands through a private journey combining exceptional resorts, privately arranged inter-island flights and experiences selected around you.

Spend three nights on each island, with time to enjoy its distinctive landscape, explore with local guides and relax at your resort.

Your journey begins on Maui and finishes on the island of Hawaiʻi.

Enquire About Hawaiian Discovery →

A green sea turtle swimming underwater in clear blue water.

Nights 1–3:

Maui

Arrive at Kahului Airport, where your driver meets you for a private transfer to Four Seasons Resort Maui at Wailea.

Begin with time beside the ocean, an afternoon at the spa or dinner overlooking the coast.

Explore more of the island with a privately guided Road to Hana excursion, a scenic helicopter flight or a sailing and snorkelling experience. Your itinerary can be as active or as relaxed as you prefer.

A large turquoise ocean wave curling over with a sandy beach and sparse trees in the background.

Nights 4–6:

Lānaʻi

Continue by private aircraft to Lānaʻi, followed by a transfer to Four Seasons Resort Lānaʻi.

Spend three nights discovering the island’s quieter rhythm. Enjoy the coastline around Hulopoʻe Bay, explore inland with a guide or arrange time on the water.

Golf, spa treatments and dining at the resort provide further ways to enjoy your stay.

Aerial view of lush green mountains meeting a turquoise blue ocean with white sandy beaches and cloudy sky.
A scenic beach with white sand, calm turquoise water, an island in the distance, and mountains under a partly cloudy sky.

Nights 7–9:

Kauaʻi

Fly privately to Kauaʻi and continue by chauffeured transfer to 1 Hotel Hanalei Bay.

Discover an island of green valleys, dramatic cliffs and extraordinary coastal scenery.

Depending on the season and conditions, experiences might include a private boat excursion along the Nā Pali Coast, a helicopter flight, guided garden visits or time exploring the island with a local guide.

Leave room to enjoy the hotel and the views across Hanalei Bay.

A couple walking by a pool with a beach, ocean, mountains, and sunset in the background. The setting appears to be a tropical resort with thatched roof and lounge chairs.

Nights 10–12:

Island of Hawaiʻi

Your final island flight brings you to Hawaiʻi, followed by a private transfer to Four Seasons Resort Hualālai.

Explore the Kona coast, discover coffee country or arrange a guided excursion focused on the island’s volcanic landscapes. Helicopter routes and volcano experiences depend on current conditions and operating restrictions.

Private sailing, snorkeling, golf and time at the resort offer a choice of ways to finish your journey.

On day thirteen, your driver takes you to your departure airport.

Volcanic eruption with lava flowing into the ocean under a cloudy sky.

Private Flights Between Islands

Inter-island flights are arranged for your traveling party through independent aircraft operators. Aircraft type, luggage allowances, airports and flight timings are confirmed in your proposal.

Private ground transfers connect your airports and resorts.

A Hawaii Journey Shaped Around You

Choose more time on the water, privately guided exploration, dining experiences or additional days at a favourite resort.

Your proposal specifies the hotels, room categories, flight sectors, transfers, selected experiences and meals included. Featured properties and activities are subject to availability.

Plan Your Hawaiian Discovery

Tell us your preferred dates, party size and what you would most like to experience in Hawaii.

Enquire About Hawaiian Discovery →

The following EXPERIENCES illustrate some of the exceptional possibilities available during your journey. All arrangements are subject to availability and individual confirmation. Only experiences expressly included in your final written proposal and booking confirmation form part of your journey.

  • A person scuba diving underwater near a coral reef, surrounded by fish and marine life.

    Maui

    Private Helicopter Tour over West Maui, Haleakalā, and Molokaʻi Sea Cliffs

    The Road to Hana with a Private Naturalist Guide

    Haleakalā Summit Sunrise with Private Transport

    Private Catamaran Charter with Snorkeling at Molokini Crater

    Sunset Whale Watching (December–April, humpback season)

    Helicopter to Hana for Private Lunch

    Maui Winery Private Tasting (Ulupalakua Ranch)

    Snorkel at Honolua Bay with a Private Guide

    Upcountry Private Farm Visit

    At Four Seasons Maui

    Dinner at Spago — Wolfgang Puck's oceanfront restaurant

    Ferraro's Bar e Ristorante (al fresco Italian)

    The Spa at Four Seasons Maui

    Three championship golf courses adjacent

    Private beachfront cabana service

    Outrigger canoe lessons from the beach

  • Several dolphins swimming in blue water viewed from above.

    Lānaʻi

    Private Catamaran along the Kaunolū Sea Cliffs

    Dive the Cathedrals — underwater lava tubes with vaulted coral ceilings

    Manele Golf Course — Jack Nicklaus signature, oceanfront

    Dinner at Nobu Lānaʻi — cliff-side omakase

    Private 4×4 tour of Lānaʻi's interior and the plantation-era landscape

    Horseback ride into the upland hills of Koele

    Visit to Lānaʻi City and the Blue Ginger Café (cultural context, not commerce)

    Puʻu Pehe (Sweetheart Rock) hike at Manele Bay

    At the property

    Hulopoʻe Bay snorkeling (spinner dolphins, resident reef)

    Hawanawana Spa — ocean-facing treatment rooms

    One Forty — oceanfront steakhouse

    Views — post-golf lunch overlooking the course and Pacific

    Private observatory for stargazing (Lānaʻi has minimal light pollution)

  • Aerial view of lush green mountains with a coastline, small houses, and a beach on an island, with the ocean in the foreground and cliffs along the shore.

    Kauaʻi

    Private Boat Charter along the Napali Coast (sea caves, waterfalls, Kalalau Valley)

    Private Helicopter Flight — Waialeale Crater, Waimea Canyon, Napali Coast

    Limahuli Garden Private Tour — endemic Hawaiian flora, botanical preserve

    Private Catamaran Charter with Snorkeling and Lunch

    Ke'e Beach and Haʻena State Park (end of the road, Napali trailhead)

    Waimea Canyon Drive with Private Naturalist

    Kauaʻi Coffee Company Private Tasting

    Private Farm Tour — Hanalei Bay taro farms

    At 1 Hotel Hanalei Bay

    ★ Welina Terrace — sunset ritual and Japanese-inspired plates

    ★ Princeville Makai Golf Course — Robert Trent Jones Jr. oceanfront design

    Bamford Wellness Spa — infrared sauna and ocean float sensory pods

    1 Kitchen — farm-to-table with bay views

    Sunset Hawaiian ritual at Welina Terrace

    Private beach cabana service at Honoiki Beach

  • Aerial view of a volcanic crater with steam rising from it and surrounding rugged terrain in shades of dark gray, black, and red.

    The island of Hawaiʻi

    Private Helicopter Flight over Kīlauea Volcano and Volcanoes National Park

    Private Boat Charter along the Kona Coast with Snorkeling at Kealakekua Bay

    Mauna Kea Summit Drive at Sunset with Private Astronomer

    Kona Coffee Plantation Private Tasting

    Private Ranch Visit in the Waimea Uplands (Parker Ranch)

    Helicopter Flight over the Northern Valleys (Waipiʻo, Waimanu)

    Private Manta Ray Night Snorkel— Kona Coast

    Private Historical Tour of Puʻuhonua o Hōnaunau — the Place of Refuge

    At Four Seasons Hualalai

    King's Pond Snorkeling with a Marine Biologist

    Dinner at 'ULU Ocean Grill + Sushi Lounge

    Hualalai Golf Course — Jack Nicklaus signature, PGA Champions Tour venue

    Miller & Lux — Tyler Florence's oceanfront steakhouse

    Beach Tree — Italian and Mediterranean beachfront dining

    Hualalai Spa — 14 treatment rooms

    Cultural Center — Hawaiian history classes and artisan demonstrations