Luxury Holidays to Hawaii
Island Hopping with a Five-Star Finish
Hawaii is where volcanic drama, lush valleys, and golden beaches create a landscape as diverse as it is breathtaking. But this is no ordinary beach escape—Hawaii offers a luxury experience infused with Aloha spirit, native culture, and world-class indulgence.
From private helicopter tours over active volcanoes to oceanfront villas, spa sanctuaries, and exclusive luaus under the stars, Awake & Wander crafts your personalised journey across the islands—whether you’re exploring Maui, Oahu, Big Island, or Kauai.
A Small Selection of our Latest Offers to Hawaii
These latest offers have been generated through our online booking system which is powered by our sister company, Jamie Wake Travel, and using our handpicked suppliers.
There will occasionally be times when offers will not show here. For example, where a destination may require more in-depth travel arrangements and will need to be tailor made by our team.
Prefer a more personal touch? We're always here to tailor your journey—simply get in touch and let us create the perfect luxury holiday to Hawaii for you.
How to Arrive in Hawaii in Comfort and Style
Hawaii is served by Honolulu (HNL), Maui (OGG), Kona (KOA), and Lihue (LIH) airports, with direct flights from the USA, Japan, Australia, and more. Awake & Wander handles VIP arrival, inter-island flights by private charter, and chauffeured transfers, ensuring smooth travel from island to island.
Best Time to Visit for Sun, Surf, and Serenity
Hawaii is a year-round destination with consistent warm temperatures. April to October is ideal for sunshine and snorkelling, while December to March draws surfers with big waves and humpback whale sightings. Awake & Wander times your visit with seasonal festivals, lava flows, and turtle nesting to create an island escape full of unforgettable moments.
The Top 4 Unforgettable Experiences and Things to Do in Hawaii
This is paradise, perfectly tailored.
1
Stay in a Private Villa or Suite at a Legendary Resort
Whether at Four Seasons Hualalai, Aman’s Wailea site, or a private Kauai clifftop villa, Awake & Wander ensures you wake up to ocean views, sunset terraces, and the soft rhythm of the waves—complete with butler service and on-demand wellness.
2
Helicopter Over Volcanoes and Waterfalls
Explore Hawaii Island’s active volcanoes, Molokai’s towering sea cliffs, and hidden rainforest valleys by air. Awake & Wander offers doors-off private flights, in-flight champagne, and exclusive landing spots for panoramic picnics.
3
Enjoy a Private Luau or Cultural Ceremony
Beyond the resorts, Awake & Wander arranges intimate hula performances, fire dancing, and feasts hosted by local chefs and cultural ambassadors. These private moments honour Hawaii’s indigenous traditions with depth and elegance.
4
Snorkel with Manta Rays or Surf with a Pro
Glide alongside gentle manta rays in the moonlit waters off Kona or ride the waves with a champion surfer in Waikiki. From paddleboarding to freediving, Awake & Wander matches you with top guides for every ocean adventure.
Why Hawaii Offers Deep Luxury with True Aloha
Luxury in Hawaii isn’t just about lavish hotels—it’s about feeling connected, welcomed, and at ease. It’s a place of raw beauty, spiritual richness, and incredible hospitality.
Awake & Wander brings together the best of each island in one fluid journey, combining refinement and authenticity for a Hawaii escape that goes far beyond the ordinary.
