The Four Seasons Resort Oahu at Ko Olina has an otherworldly infinity pool.
(1 of 5)
Heavenly views from the penthouse suite.
(2 of 5)
At the Four Seasons Resort Hualalai, new Nests—lounge beds that come with their own wait service, a stocked minibar, exclusive lotions—swivel to follow the sun.
(3 of 5)
Horseback riding is one of many thrilling adventures offered on Lanai.
(4 of 5)
Seven pools of varying shapes grace the Four Seasons Resort Hualalai.
(5 of 5)
The Hawaiian islands are shaped like a skeletal arm, with the Big Island as the shoulder, Lanai and Maui working together as a bicep, and Oahu as the wrist leading to the palm of Kauai. The water oscillates between teal and rich navy, depending on what atoll you drop in. Culture here is more ancient than even recorded and all that you imagine of this tropical nirvana: the lavish fauna, the aroma of leis, the ornate hula and the proud people. I soon realize when visiting three of its islands that it is far greater and aggrandized.
Being a New Yorker on a quest to unplug, I discover there is a perfect stage-by-stage graduation to take for detaching from work and stress. First stop: the five-star Four Seasons Resort Oahu at Ko Olina.
STOP 1: KO OLINA, OAHU
Four Seasons Resort Oahu at Ko Olina sits along the leeward side of the island’s more desert landscape. Although the scenery is drier and less lush on the way to the resort, the velvety white sand and turquoise sea you envision is prevalent in the palm-tree lined crescent-shaped coves and lagoons enveloped by the resort.
The vast wraparound terrace of the two-bedroom, 17th-floor penthouse suite ($19,000 per night) with full kitchen and dining room affords stunning vistas of all sides of the island. Off our balcony, my husband and I spot Kaena Point at the western tip of Oahu and make plans to see it the next day, when we witness dolphins, seals and a rocky desolate coastline that makes us feel like we’re the only people left on Earth.
Dining-wise, the restaurant lineup at Four Seasons Resort Oahu at Ko Olina includes some of the best on the island—and that’s competing with swanky Waikiki’s all-star offerings. Noe is a can’t-miss fine-dining concept by a chef who has worked in Michelin-starred restaurants and specializes in the Southern Italian food of the Amalfi Coast, but is equally skilled in Japanese cuisine. The ahi tuna “panzanella” brushed in lemon and olive oil is a remarkable melding of the two opposing fares, as is the Kona lobster spaghetti pomodoro. Rooms from $545, suites from $1,100
STOP 2: KONA, BIG ISLAND
On the Big Island, there’s nothing that can prepare you for the black-lava North Kona coast or the rocky shoreline only steps from the villa suites at the Four Seasons Resort Hualalai. Kona itself is verdant and lush, so Hualalai was designed and built with the Hawaiian aesthetic and nature as its guide.
This is by far the more active, outdoorsy and adventure-filled resort, and the seamless next step we need to disconnect from city life. All the suites and villas in the 243-room resort sit in two-story bungalows separated by four saltwater coves, each with its own vibe. We notice one is quiet, another social, one active with families and the last teaming with singles. Seven pools of all shapes and sizes are peppered throughout the property.
It’s immediately apparent upon arrival that Hualalai is a world-class golf destination. The Jack Nicklaus-designed course is home to the PGA Mitsubishi Electric Championship. There’s also tennis, outdoor rock climbing and unlimited activities, which means boredom is impossible. The property is the only one of the three that has a dedicated cultural center. All of the Four Seasons resorts put on cultural events and activities that connect you with the history of the islands, but at this center, you can experience lei-making, ukulele or hula lessons; explore historic salt flats; learn ancient star navigation; or go on the water with Alaka‘i Nalu ocean ambassadors. Rooms from $859, suites from $1,659
STOP 3: LANAI CITY, LANAI
Flying in over electrifyingly steep cliffs and cerulean waters to the remote island of Lanai is akin to arriving in the Hawaii that existed 60 or 70 years ago. We land on a single airstrip with a tiny outpost building, and transportation from Four Seasons Resort Lanai takes us up a steep mountain pass. Once over the top, the path breaks into a winding road all the way down the other side of the mountain to the remote resort. Larry Ellison, the co-founder and chief technology officer of Oracle, owns 98 percent of Lanai. Two years ago, he completely renovated the resort and updated the technology throughout the property—think wristband room keys, high-tech televisions and touch-screen everything.
The open-air rooms, koi ponds and symmetry of the tropical gardens are paired with some of the most beautifully appointed furnishings we’ve seen in all of our years of luxury travel. The staff is inherently local and a feeling of real connection leaves us with the authentic aloha feeling.
Horseback riding is a cultural tradition on Lanai. We take a two-hour trail ride up the red-clay mountains into a forest filled with indigenous ironwood trees. If you’d rather explore the island by sea, take a catamaran out for a group snorkel sail to the secluded Shark’s Cove.
Lanai has some of the most extraordinary dining options: Nobu Lanai overlooks Hulopoe Bay, and we have our wagyu beef served sizzling on a lava rock for pure high-drama dining. Rooms from $1,150
Originally published in the October/November issue of Silicon Valley