Hawaii, USA
Island Hopping Through Paradise
A fully bespoke luxury journey, designed entirely around you.
DURATION
12 Nights
BEST TIME TO GO
April – May & September – November
IDEAL FOR
Discerning travelers seeking an extraordinary experience
A bespoke 12 nights journey through Hawaii, USA — designed entirely around your preferences, pace, and vision of extraordinary. Every detail is curated by advisors who know this destination from the inside.
Hawaii's island chain offers far more than beaches and mai tais. From Oahu's cosmopolitan energy to the Big Island's volcanic moonscapes, Maui's upcountry estates to Kauai's roadless wilderness, each island reveals distinct character. This journey curates the archipelago's finest — Michelin-starred tables, helicopter journeys into untouched valleys, private yacht charters between islands, and accommodations where indigenous culture meets world-class luxury.
Begin on Oahu at the legendary Halekulani, with AAA Five Diamond dining and private cultural explorations of Pearl Harbor and Iolani Palace. Cross to Maui for a pre-dawn Haleakalā sunrise, upcountry wine tastings, and the iconic Road to Hana. The Big Island delivers volcanic drama at Hualalai — lava fields, manta ray encounters, and ancient petroglyph parks. The journey culminates on Kauai's Garden Isle, with Na Pali Coast boat charters and helicopter flights over Waimea Canyon.
Every element is fully bespoke — from inter-island flights and private transfers to priority restaurant reservations and 24/7 concierge support. Best experienced during April–May and September–November, this 12-night journey can be extended to include Lanai or Molokai, or shortened to focus on fewer islands.
The Journey
Your Itinerary
Chapter 01
Chapter 01 — Oahu: Urban Sophistication Meets Island Culture
Touch down in Honolulu and transfer to Halekulani on Waikiki Beach. Settle into your ocean-view suite before sunset cocktails at House Without A Key, then dinner at La Mer (AAA Five Diamond).
Chapter 02
Chapter 02 — North Shore & Culinary Exploration
Private guide leads you to the North Shore's legendary surf breaks. Lunch at Haleiwa, then return to Honolulu for dinner at Senia, one of Hawaii's most acclaimed restaurants.
Chapter 03
Chapter 03 — Pearl Harbor & Cultural Immersion
Morning at Pearl Harbor with private historian. Afternoon exploring Iolani Palace and the Bishop Museum, then farewell dinner at MW Restaurant featuring modern Hawaiian cuisine.
Chapter 04
Chapter 04 — Maui: Upcountry & Coastal Elegance
Inter-island flight to Maui. Check into Four Seasons Resort Maui at Wailea. Afternoon exploring the resort's oceanfront setting before dinner at Spago Maui.
Chapter 05
Chapter 05 — Haleakalā & Upcountry
Pre-dawn ascent to Haleakalā summit for sunrise above the clouds. Descend through upcountry Maui for wine tastings at MauiWine, then lunch at O'o Farm overlooking the valley.
Chapter 06
Chapter 06 — Road to Hana
Private driver navigates the legendary Road to Hana. Stop at waterfalls, black sand beaches, and roadside fruit stands before reaching Travaasa Hana for lunch and exploration.
Chapter 07
Chapter 07 — Big Island: Volcanic Landscapes
Fly to Kona. Transfer to Four Seasons Resort Hualalai, the exclusive Big Island retreat. Settle in before dinner at ULU Ocean Grill.
Chapter 08
Chapter 08 — Volcanoes National Park
Full-day exploration of Hawaii Volcanoes National Park with expert volcanologist guide. Witness active lava flows (conditions permitting) and crater formations.
Chapter 09
Chapter 09 — Kona Coast & Marine Life
Morning snorkeling or diving at Kealakekua Bay. Afternoon at Puako Petroglyph Park, then sunset manta ray snorkel experience off the Kona coast.
Chapter 10
Chapter 10 — Kauai: Garden Isle Wilderness
Fly to Lihue. Helicopter transfer to 1 Hotel Hanalei Bay. Settle into your ocean-view suite overlooking Hanalei Bay and Bali Hai.
Chapter 11
Chapter 11 — Na Pali Coast
Private boat charter along the Na Pali Coast — dramatic sea cliffs accessible only by water. Snorkel at secluded coves, then picnic lunch on a remote beach.
Chapter 12
Chapter 12 — Waimea Canyon & Farewell
Helicopter tour over Waimea Canyon (the "Grand Canyon of the Pacific") and into roadless valleys inaccessible by land. Farewell dinner at Tidepools restaurant.
Make This Itinerary Yours
Every Haute Black journey is crafted around you — your passions, your pace, your vision of extraordinary. Tell us about yourself and we'll create something entirely yours.
Where You'll Stay
Featured Properties
Halekulani, Oahu
Legendary Waikiki beachfront property with La Mer restaurant (AAA Five Diamond), oceanfront setting, and timeless Hawaiian elegance.
Four Seasons Resort Maui at Wailea
Luxurious oceanfront resort with three infinity pools, Ferraro's Bar e Ristorante, Spago Maui, and the award-winning spa.
Four Seasons Resort Hualalai, Big Island
Exclusive Kona Coast retreat with only 243 rooms, seven pools including King's Pond saltwater snorkel lagoon, and ULU Ocean Grill restaurant.
1 Hotel Hanalei Bay, Kauai
Sustainable luxury on Hanalei Bay with ocean-view suites, farm-to-table Hihimanu restaurant, and proximity to Na Pali Coast adventures.
Good to Know
Questions About This Journey.
Completely. Every HauteBlack journey is a starting point, not a fixed package. Your dedicated travel advisor will reshape every element — accommodations, pacing, dining, private guides, and experiences — entirely around your preferences, travel style, and what you want to remember. Nothing is off the shelf.
For peak-season travel and premium properties — particularly safari lodges like Singita Ebony Lodge or Delaire Graff Estate — we recommend booking 6 to 12 months in advance. For more flexible dates and destinations, 3 to 6 months is typically sufficient. Your advisor will always tell you honestly what's achievable in your timeframe and find alternatives if first-choice properties are unavailable.
No. All HauteBlack journeys are available without membership. You work with a dedicated travel advisor and receive Virtuoso preferred partner benefits — complimentary upgrades, resort credits, daily breakfast, and VIP arrival — on every qualifying stay, membership or not. Membership adds waived planning fees, a dedicated senior advisor, priority access to private events, and deeper concierge support.
A dedicated HauteBlack travel advisor contacts you within 24 hours — usually sooner. They'll start with a conversation, not a form. You'll discuss your vision, travel style, dates, and any preferences. From there, your advisor builds a fully bespoke itinerary proposal. There is no obligation and no planning fee for the initial consultation.
Before You Go
What to Expect
Entry requirements for Hawaii, USA vary by nationality — your HauteBlack advisor will confirm visa requirements, vaccination recommendations, and optimal travel timing specific to your passport and travel dates. We recommend beginning the planning conversation at least 60–90 days before your intended departure.
Every HauteBlack itinerary is fully bespoke. While the journey outlined above represents our curated recommendation for Hawaii, USA, your dedicated travel advisor will tailor every element — from accommodations and dining to private guides and cultural immersions — to match your preferences, pace, and travel style.
Best experienced during April – May & September – November, this 12 Nights journey can be extended, shortened, or combined with neighboring destinations. Whether you're celebrating a milestone, traveling as a family, or seeking a private retreat, we adapt the experience to you.
Your Advisor Takes Care Of:
- ◆Private airport transfers and in-destination transportation
- ◆Hotel reservations and room upgrades
- ◆Restaurant access and private dining arrangements
- ◆Guided experiences and exclusive site access
- ◆24/7 support before and throughout your journey
Designed by a HauteBlack travel advisor with direct knowledge of this destination and relationships at every featured property. Meet our advisors →
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BEGIN YOUR JOURNEY
Ready to Make This Journey Yours?
Every detail can be tailored to your vision. Our travel specialists handle everything from first inquiry to final farewell.
Non-members welcome. No membership required.