Oʻahu, Hawai'i: The Island's Town & Country Tour

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Advisor - Katie Stratton
Curated By

Katie Stratton

  • O‘ahu

  • Tropical Vacations

  • Beaches

  • Food & Wine

  • Island

Oʻahu, Hawai'i: The Island's Town & Country Tour
Curator’s statement

Many people think Oʻahu is just one thing. However, the true magic of the island lies in its elegant duality: the raw, expansive beauty of the North Shore versus the sophisticated, buzzing energy of Waikiki. To truly experience Oʻahu, you shouldn’t choose between “country” and “town”—you should experience both. I recently explored how to seamlessly combine these two worlds into one transformative luxury vacation.

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Where to stay

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The North Shore adventure with luxurious elegance: The Ritz-Carlton O'ahu, Turtle Bay

If you view vacation as a launchpad for action, start here. Located on a massive 1,300-acre newly renovated peninsula, this property is an outdoor sanctuary. It’s perfect for families and active travelers who want room to explore the north shore of O'ahu.

  • The vibe: Expansive, active, and nature-focused.

  • What to do: Leverage the vast grounds for horseback riding, explore 12 miles of hiking and biking trails, or play on the new pickleball courts. The on-site kayaking with sea turtles is unforgettable.

  • Where to stay: For the ultimate experience, book one of the 42 Ocean Bungalows. They offer immediate beach access and a level of seclusion that turns the resort into a private retreat.

View from Club Room at Ritz Carlton Turtle Bay

The transition to Waikiki reveals a completely different style of luxury. Here are two urban oases that offer serenity in the city:

The cultural icon: Halekulani

Known as the “House Befitting Heaven,” Halekulani is for the traveler seeking quiet refuge and timeless elegance. Despite being in the heart of Waikiki, its five-acre footprint feels like a serene sanctuary.

  • The vibe: Tranquil, historic, and culturally rich, famous for its calming “seven shades of white” aesthetic.

  • The highlights: The dining is world-class, anchored by Hawai’i’s only AAA Five-Diamond restaurant, La Mer. But don’t miss the sunset ritual at House Without A Key, where a signature Mai Tai and hula beneath the century-old Kiawe tree are mandatory traditions.

View from Diamond Head room at Halekulani

The private “mansion in the sky”: Espacio - The Jewel of Waikiki

Espacio is designed for the ultimate in privacy. With only one 2,250-square-foot suite per floor, it offers full residential amenities with five-star hotel service.

  • The vibe: Exclusive, modern, and incredibly spacious.

  • Perfect for: High-end multi-generational families who need space to connect and separate. The in-suite kitchens allow for quiet family dinners, while dedicated butlers manage every whim.

  • The highlights: The rooftop Champagne and Caviar sunset experience is an intimate indulgence, as you have the entire rooftop booked for your own enjoyment

View from Espacio

Insider tips for your Oʻahu journey

  • At Ritz-Carlton Turtle Bay: Upgrade to a Club Room. On such a sprawling property, having exclusive access to five different dining experiences throughout the day adds immense convenience and value.

  • At Halekulani: Take advantage of the "For You, Everything" program. It offers complimentary access to top cultural sites like the 'Iolani Palace and the Bishop Museum, adding another level of Polynesian insights to your stay.

  • Must-eat: At Halekulani's Orchids restaurant, the breakfast pop-overs are legendary—order them with the lilikoi butter. At Espacio, secure a reservation well in advance for the masterfully executed tasting menu at Mugen and wine pairings from the masterful sommelier.

Need to know

Other highlights to visit:

Polynesian Cultural Center. The Polynesian Cultural Center offers a holistic and immersive experience that goes beyond just a meal and a show. It aims to educate and entertain visitors by allowing them to truly step into the diverse cultures of Polynesia.

For more inspiration and insider recommendations, visit our O'ahu page.

Advisor - Katie Stratton

Travel Advisor

Katie Stratton

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