As our plane descended towards the landing strip, the first thing I noticed about the island of Lanai was the lack of lush, jungle-like greenery and broad sandy beaches typical of Hawaii. Instead, my view held rugged, dramatic cliffs and a vast landscape dotted with dark green pine trees and dusty clay terrain dropping into the deep blue Pacific. A hidden gem in the Hawaiian archipelago, Lanai starkly contrasts with the bustling tourist destinations of Hawaii. This secluded island, once the world’s largest pineapple plantation, has evolved into a serene and exclusive getaway for those seeking respite from the fast-paced world.

For years, I’ve dreamt of taking a vacation that would give me the time and space to focus solely on my well-being. In an age when wellness and self-care have become the cornerstones of a fulfilling life, many resorts have developed wellness programs, from sleep-focused retreats to day-long immersions in nature. Finding the right blend of personalization and guidance is key. It’s easy to slip into a wellness program when surrounded by experts to help you along the way, but it’s much more complicated when you’re back in New York City trying to do breathwork on the subway.

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Courtesy of Sensei Lanai Four Seasons

A Personal Wellness Journey

When Four Seasons Sensei Lanai landed on my desk, it had all the right ingredients. The brainchild of tech innovator Larry Ellison and renowned physician Dr. David Agus, who envisioned a retreat where guests can embark on a holistic journey of self-discovery and renewal, Sensei is a sanctuary for those seeking a transformative experience.

The term “Sensei” itself, meaning teacher or mentor in Japanese, underscores the resort’s commitment to guiding guests toward their personal wellness goals. Sensei’s Rest & Recovery program was developed due to guest feedback—the many people who traveled to Lanai seeking to improve their sleep and recover from the stress of everyday life. Guests can customize their itineraries with the guidance of dedicated wellness mentors who provide expertise in fitness, nutrition, mindfulness, and more. The resort’s approach is rooted in science and tradition, fusing the latest advancements in health with age-old practices like Japanese forest bathing, yoga, and mindfulness meditation.

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My journey began two weeks prior on a call with my “sensei.” The introductory call aimed to establish goals for my trip—areas of concern, challenges in my life, personal preferences, eating and sleeping habits, and anything else that I wanted to concentrate on. I had several very clear areas of focus—improved sleep and getting more time to myself. I was also processing a lot of grief that seemed like it was on an endless loop. Based on that first call, my sensei put together a personalized plan that I would follow and, as it turns out, would be adjusted a bit during my trip.

Shortly after my call, I received a WHOOP device in the mail. WHOOP is a wearable fitness tracker and health monitoring system designed to help individuals optimize their performance, recovery, and overall well-being. The instructions were to wear the WHOOP in the weeks leading up to my trip to provide data to my sensei, give her insight into my behavior, and help her personalize my program. This is the part where you start to think a lot about how you spend your time, how well you’re sleeping, how much alcohol you consume, and how much stress you’re under.

Traveling to the island means a connecting flight through Honolulu or Maui, and I discovered that stopping over en route can be an excellent way to begin the shift towards wellness. I began my rest and recovery vacation in Honolulu to recharge from the 10-hour flight and acclimate to the time change. By all accounts, it was a pro move. When it was time to go, Sensei Lanai sent a car to pick me up and drop me at the Lanai Air hangar at HNL for a semi-private, 25-minute flight to the island. The journey was officially on. And I had no idea what was going to happen.

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I disembarked from the plane, dropped into a white Tesla, and drove slowly to the resort, passing through Lanai City, the compact town center. The resort is nestled in the island’s mountains, about a 20-minute drive from the beach. The air is cooler, and there’s a more interesting weather experience at Sensei. The grounds are lush, with beautifully manicured trees, plants, and flowers surrounding the pathways connecting buildings to outdoor experiences. The main lobby feels like a vacation home with its sprawling wrap-around porch, floor-to-ceiling windows, and fireplaces dotted throughout. Sensei Lanai is also known for its incredible art collection: The resort’s commitment to blending art and environment is evident in every corner, where carefully curated works adorn the tranquil spaces. Part of the wellness experience, the art serves as a portal to connect with the island, its culture, and one’s senses.

The guest rooms are peaceful and cloud-like, designed in shades of white and natural wood, each with its own balcony or lanai—the perfect place to rest your head after a day of wellness activities and adventure.

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Fernando Botero, Dancers, 2012, Bronze, ©Fernando Botero, Photo by Austin John

A Custom, Flexible Plan

I met with my sensei to review my itinerary on the day I arrived. We reviewed the data captured by the WHOOP device and dug deeper into the purpose of my stay. The days were divided into three modes defining the day’s events: Movement, Nourishment, and Rest. Each day included activities to help me reach my stress-reduction goals, sleep better, and experience less pain. Though the activities didn’t increase in intensity over my five-day stay, it required a different level of attention and effort. The first day began with Yin yoga, a slow-paced style with poses are held for 3-5 minutes—a great way to refresh your body after a long plane ride.

There were several activities on my itinerary that I’d never tried before—a sound bath, aerial yoga, and perhaps the most intimidating, “Reframing Resistance” at Adventure Park. The adventure park was scheduled for day three, presumably after I’d gotten my body ready for a more intense workout and my mind more relaxed. The only thing I knew going into it was that it involved trees. This is the point in the story when I should mention that the itinerary designed for me was not set in stone—I was free to swap out or skip activities if I chose to do so. I didn’t. The point of the journey was to reconnect with myself to heal and feel better, which included pushing myself. I will admit that it helped that I was surrounded by such incredible natural beauty and the generous spirit of the staff.

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The adventure park is nestled among Lanai’s many Cook Island Pines—tall, slender trees with a distinctive, straight trunk and symmetrical, tiered branches. They are known for their striking appearance, resembling large, green exclamation points dotting the island’s landscape. It was in the trees that I would spend two hours going through a series of mental and physical obstacles. The primary activity was climbing. I am not a climber and learned during the session, not unexpectedly, that I fear heights. Harnessed in and helmeted, the direction was to climb up a tree to reach a log suspended 25 feet above ground, walk across the log to another tree, and rappel back down. From the ground, this looked entirely doable.

Facing My Fears

I reached the top of the tree and stepped onto the log. This is when I realized that I might have a fear of heights. My guide, AJ, told me to close my eyes, lean into the fear, and activate the breathwork I’d been working on to help manage the stress. The point, he explained, was to acknowledge the fear and accept it instead of trying to fight it. I did—and I still decided to rappel down instead of cross the log. AJ told me to let go of the tree I’d climbed up and step out onto the log so I could position myself to rappel down. I did as he instructed, then turned around, leaned back into my harness, and was safely guided to the ground. As I descended, I looked up at the log where I’d been standing and realized I’d made it halfway across. Maybe it wouldn’t have been as frightening as I’d imagined to have continued across to the other tree,  after all.

The adventure park offers a variety of activities to address personal challenges or just have fun, such as ziplining through lush forests, off-road tours exploring Lanai’s rugged terrain, and a two-story aerial course over water with bridges, puzzles, and obstacles (you’re harnessed in so you can navigate through safely).

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Courtesy of Sensei Lanai Four Seasons

Thankfully, each day ended with a 120-minute spa treatment in a private Hale—private teak and glass houses that feature soaking tubs, steam shower, sauna, hot and cold plunge pools, and an outdoor shower. Each spa session included an hour massage, customized to my needs, followed by an hour of private time in the Hale with tea and fruit providing a burst of nourishment.

Each evening, dinner was at Nobu, the culinary backbone for the “nourishment” part of my program. The menu blends traditional Japanese flavors with contemporary innovation, and every meal is a gastronomic journey, so clean and fresh that you know you’re doing something right for your body. I spent 90 minutes of “mindful eating” with Sensei’s staff dietician as part of my program, and even though the diet was not a primary area of concern, I was reminded of the pleasure of a slow meal, savoring every bite and allowing space for both conversation and silent moments.

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A Well-Balanced Experience

Between programmed sessions, I had plenty of time to enjoy the saltwater pool, walk through the gardens, and even pull off a sunset sail—an activity co-managed with the Four Seasons Lanai. This sister property overlooks Hulopoe Bay.

My sensei closely managed my Rest and Recovery journey at Sensei Lanai. We met each day for an hour to discuss what I was experiencing during my stay and whether we needed to adjust anything. She was intelligent and enthusiastic, and our conversations were low-key therapy sessions that included learnings from the data being tracked by my WHOOP device. These gave key insights, as it turned out, to my patterns and how the program at Sensei was changing my behavior.

Four Seasons Sensei Lanai is more than a wellness retreat; it’s a soulful escape, where you can tap into the power of combining ancient wisdom with modern science. I left Sensei feeling better than I’d felt in a very long time, armed with tools to help me live a harmonious life. And if I need reminding, I have a detailed recap of the program and the insights I’d gained while I was there, which my sensei shared with me after I’d returned home. This is a destination that is indeed worth the journey.