Sample Itinerary · Hawaiʻi · Three Islands

Hawaii Island Hopping 10-Day Tour

Oʻahu · Maui · Hawaiʻi Island

Duration10 Days · 9 Nights
RouteOʻahu · Maui · Hawaiʻi Island
TransportPrivate Transfers · High-Speed Rail
Best ForFirst-Timers · Couples · Families
10 Days · 9 Nights
Oʻahu · Maui · Hawaiʻi Island
Private Transfers · High-Speed Rail
The Classic Three-Island Journey
Sample — Fully Customisable

This is a sample itinerary — for inspiration only. Every Juniper trip is designed from scratch around you. Many clients travel a very similar route — if this resonates, book a free consultation and a specialist will build something just like it (or better) specifically for your travel style, dates, and group.

1
Day One

Arrive in Honolulu, Oʻahu

Honolulu · Waikīkī

Aloha. A private driver meets you at Honolulu and brings you to your hotel along Waikīkī Beach. Settle in, then a sunset stroll on the sand and your first mai tai as Diamond Head turns gold.

Your specialist keeps the first evening easy before the islands open up.

Private airport transfer Waikīkī check-in Evening at leisure
Overnight: Honolulu (Oʻahu)
2
Day Two

Oʻahu — History, Coast & Country

Oʻahu

A full day with a private guide — the Pearl Harbor memorials, the lush windward coast, and the legendary surf of the North Shore.

Hike Diamond Head for the classic view over Waikīkī, or snorkel a protected cove. The day is shaped around your pace.

Pearl Harbor North Shore Diamond Head
Overnight: Honolulu (Oʻahu)
3
Day Three

Oʻahu to Maui

Maui · Wailea / Kāʻanapali

A short morning flight to Maui, the Valley Isle. A private driver transfers you to your resort on the sunny west or south shore.

The afternoon is yours — the beach, the pool, and a Pacific sunset to ease into Maui time.

Inter-island flight Ocean-view resort Beach at leisure
Overnight: Maui
4
Day Four

Maui — The Road to Hāna

Hāna Highway

The famous Road to Hāna with a private guide-driver, so you simply take it in — waterfalls, bamboo forests, black-sand beaches, and lava coastline through old Hawaiʻi.

Stops for swimming, banana bread, and the views that make this one of the world's great drives.

Road to Hāna Waterfalls Black-sand beaches
Overnight: Maui
5
Day Five

Maui — Haleakalā & the Sea

Haleakalā · Molokini

An optional sunrise above the clouds at the summit of Haleakalā, then the day at sea — a snorkel sail to the Molokini crater, with sea turtles and, in winter, the song of humpback whales.

The afternoon is for the beach or the spa.

Haleakalā summit Molokini snorkel Whales (in season)
Overnight: Maui
6
Day Six

Maui to Hawaiʻi Island

Kona · Kohala Coast

A quick hop to the Big Island and a transfer up the Kohala Coast, where black lava meets white sand and the island's great resorts.

Settle in and watch the sun drop into the Pacific as the scale of Hawaiʻi Island begins to reveal itself.

Inter-island flight Kohala Coast resort Pacific sunset
Overnight: Hawaiʻi Island
7
Day Seven

Hawaiʻi Island — Volcanoes & Lava

Hawaiʻi Volcanoes National Park

A guided day in Hawaiʻi Volcanoes National Park — steaming craters, lava tubes, and the raw, living edge of the earth at Kīlauea.

Coffee in the hills of Kona on the way back, and the volcano glowing after dark if the timing is right.

Kīlauea & craters Lava tube walk Kona coffee
Overnight: Hawaiʻi Island
8
Day Eight

Hawaiʻi Island — Coast & Manta Rays

Kona · Kohala Coast

A relaxed day on the Kohala Coast — beaches, snorkeling, and the spa.

After dark, the unforgettable guided night snorkel with the giant manta rays that gather off the Kona coast.

Kohala beaches Snorkeling & spa Manta-ray night dive
Overnight: Hawaiʻi Island
9
Day Nine

Hawaiʻi Island at Leisure

Kohala Coast

A final island day as you please — the beach and the pool, a last snorkel, or the waterfalls of the Hilo side.

A farewell dinner by the water to close the journey.

At leisure Beach & spa Farewell dinner
Overnight: Hawaiʻi Island
10
Day Ten

Depart

Kona / KOA Airport

A last morning by the water, then a private transfer to Kona for your flight home — three islands that ran from Waikīkī to the Road to Hāna to the living volcanoes.

Your Juniper specialist remains reachable throughout departure day.

Private airport transfer Departure 24/7 specialist support

Love this itinerary? Make it yours.

This is a sample custom route — a starting point, not a fixed package. Many clients travel something very close to this. Book a free consultation and a specialist will build from here.

Accommodations
Eco-luxury lodges, boutique hotels, and beachfront retreats — chosen based on your preferences and travel style.
Transportation
Private transfers, high-speed rail, self-drive, or a mix — all confirmed before you travel.
Experiences
Pre-arranged tours and activities built around your interests — entrance tickets sorted, no queuing.
Available Experiences

Activities on this itinerary

Your specialist pre-arranges the right luxury experiences based on your interests and travel style. These are the custom experience types available on this route — specific choices are made with you, not for you.

Pearl Harbor
Oʻahu
Diamond Head & Waikīkī
Oʻahu
North Shore Surf
Oʻahu
Road to Hāna
Maui
Haleakalā Sunrise
Maui
Molokini Snorkel
Maui
Hawaiʻi Volcanoes NP
Kīlauea
Manta-Ray Night Dive
Kona
Kona Coffee Country
Hawaiʻi Island
Kohala Beaches
Hawaiʻi Island
Inter-Island Flights
Throughout
Ocean-View Resorts
Throughout

Activities are selected and pre-booked with your specialist based on your interests — not all activities are included in every trip version. Availability varies by season.

Your Top Travel Specialists

The people who will design your Hawaii trip

You work directly with a specialist who knows Hawaii deeply — not a call center or booking agent. Every consultation is with someone who has been there, stayed in those hotels, and knows the country inside out.

Your Hawaii Specialist
Hawaii · Custom & Honeymoon

Your Hawaii Specialist

A dedicated Hawaii specialist designs your trip from scratch — the right eco-lodge, private naturalist guides, the best windows for wildlife and weather, and the balance of soft adventure and beach time.

Book a Consultation
Your Hawaii Specialist
Ireland · Scotland · UK · Iceland

Your Hawaii Specialist

From volcano-view lodges to beachfront retreats, your specialist arranges every transfer, naturalist guide, and experience before you travel.

Book a Consultation
Questions

About this itinerary

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