Waikiki: Designing a Vacation Around Wellbeing, Curiosity and Play
When I started planning our trip to Waikiki, I gave the concierge team at The Ritz-Carlton Residences, Waikiki Beach a somewhat different brief.
I wasn’t looking for a list of the top ten things to do in O’ahu.
I wanted to create a vacation that was interesting, restorative and fun.
That distinction shaped the trip.
Rather than filling every day from morning until night, we built the week around a handful of experiences that gave us opportunities to move, learn, explore, recover, eat well and simply enjoy being somewhere different.
And, as often happens when you travel, the itinerary changed once we arrived.
Night One: Start With a Sense of Place
Our first evening began with My Story of O’ahu, one of the Ritz-Carlton’s complimentary cultural experiences.
As the sun was setting, a Hawaiian language student shared a love of the island through oli, or chant.
It was a simple way to begin a trip, but an important one. Instead of immediately approaching O’ahu as tourists looking for things to do, we started by learning something about the place we were visiting.
There is something to be said for priming the mind before an experience. A little context changes what you notice afterward.
From there, we headed over to the mall in search of another Hawaiian essential: slippers.
The concierge had recommended Island Slipper at the Royal Hawaiian Shopping Center and OluKai at the Sheraton Waikiki, both within easy walking distance of the hotel.
New slippers secured, we managed to get the last seating of the evening at Restaurant Suntory.
Culture, walking, shopping and a great dinner made for a pretty good first night.
Day Two: Make the Beach Easy
The next day, we ventured out to Waikiki Beach via the Moana Surfrider, a short walk from the hotel.
One of the things I liked about this approach was its simplicity. The Moana Surfrider has a beachfront bar with live music, which added to the beach experience without requiring us to plan another activity.
We could swim, spend time on the beach, listen to music and simply enjoy Waikiki.
Beach tip: Wear your bathing suit and cover-up from the hotel. Leave your valuables behind, put your phone in a waterproof case and bring towels and floaties. The less you have to worry about once you reach the water, the better.
And if lying on the beach isn’t enough activity for you, beginner surfing lessons are available farther down the beach.
Sometimes wellbeing is less about adding another activity and more about removing the friction from doing something you already enjoy.
Becoming Beginners Again
We made it back to the Ritz-Carlton in time for one of the experiences I had been most curious about: the B+HARI Brain Wellness Workshop.
B+HARI describes its method as using intentionally designed movement and creative experiences to influence how the brain and body communicate, with the goal of supporting cognitive flexibility, clarity and resilience.
It was unlike a conventional fitness class.
We experimented with fascia release, stretching and strengthening, but also with imagination. Instead of simply adding more physical resistance, we explored using the mind to create the sensation of weight. Movement became playful. Art and creativity became part of the experience.
For me as a Pilates teacher, this was one of the most interesting parts of the trip.
It left me thinking about how much more we can do with imagery in movement—and about the relationship between the brain, nervous system and fascia.
Travel can be restorative. But it can also be a wonderful opportunity to become a beginner again.
We ended the evening back in the water, this time with a hot tub and swim at the hotel.
Beach. Brain. Body. Recovery.
That turned out to be a pretty good day.
Day Three: Get Into the Pacific
The next day brought one of our biggest adventures: a semi-private Turtle Snorkel & Catamaran Cruise with Hawaii Ocean Charters.
Our guides, Sam and Hailey, did a great job of reviewing the snorkeling basics before safely guiding us into the water.
Once we were in, they pointed out the sea turtles and fed the tropical fish, bringing even more activity and colour into the experience.
The adventure wasn’t limited to what we saw underwater. On the ride to and from the reef, they pointed out landmarks along the Honolulu skyline, giving us another perspective on the place we had been exploring on foot.
For anyone considering a turtle experience, it’s also important to remember that Hawaii’s green sea turtles are protected. Visitors need to give them their space rather than trying to approach or touch them.
Snorkeling is also a wonderful reminder that movement doesn’t need to look like exercise.
You’re breathing differently. You’re navigating an unfamiliar environment. You’re paying attention to your surroundings. You’re moving continuously.
And you’re probably not counting a single repetition.
Trade the MOKE for a Jeep
Our original plan had been to rent one of the Ritz-Carlton’s little electric MOKEs. The concierge had suggested using one to drive to Manoa Falls after the guided Story of Manoa experience became unavailable.
Instead, we rented a Jeep from Enterprise.
That change gave us considerably more freedom to explore the island over the next two days.
On our first drive, we headed east, stopping at outlooks and beaches along the way. One of the discoveries was Kaiona Beach Park, a beach preferred by locals and a very different experience from busy Waikiki.
This became one of my favourite parts of the trip: not having every stop predetermined.
Drive. See something interesting. Stop. Walk around. Get back in the Jeep.
Travel becomes much more playful when there is room for discovery.
Head North
The next day, we headed in the opposite direction.
We drove north to Wahiawa to visit a coffee plantation and roaster before continuing to Waimea Valley.
There, the day’s movement came from walking through the Botanical Gardens before swimming in the waterfall.
It was exactly the kind of experience I had hoped the trip would include: movement, nature, learning and something that felt completely different from an ordinary day at home.
From Waimea, we continued to Haleiwa and finished the day watching the sunset at Haleiwa Beach, across the street from the Beach House restaurant.
There wasn’t much more that needed to be added.
Sometimes sunset is the activity.
Leave Room for Food
Food became part of the exploration throughout the week rather than something we needed to schedule every night.
And on our final day, we discovered Stix Asia.
The modern, exceptionally clean food hall offers a variety of authentic Asian food in one location, making it an easy place to wander, choose whatever appeals to you and share different things.
It was a fitting way to finish a trip that had become less about following an itinerary and more about exploring.
A Different Way to Think About Vacation
Looking back, what strikes me is that the trip wasn’t really about pursuing “wellness.”
We didn’t go to a wellness retreat.
We went to Waikiki.
But we intentionally built different dimensions of wellbeing into an ordinary vacation:
Move. Learn. Explore. Play. Recover. Connect. Eat well. Rest.
We walked beaches and botanical gardens. We swam in the Pacific and under a waterfall. We snorkeled with sea turtles. We experimented with an entirely new form of brain-body movement. We drove around the island without needing every stop mapped out in advance. We ate great food. We watched the sunset.
And we spent time in the hot tub doing absolutely nothing productive.
Perhaps that’s the bigger lesson.
Wellbeing doesn’t have to be another program we follow or another item on a list of things we’re supposed to accomplish.
It can be woven into the experiences we’re already having.
In fact, the itinerary worked best when we had enough structure to get us moving—and enough space to change our minds once we got there.
Strong body. Calm mind. Balanced life—even when you’re away from home.
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