My First Solo Trip: What O‘ahu Taught Me About Slowing Down, Cherishing Legacies, and Moving Forward

I had never traveled alone for leisure, not even in my youth. After decades of making travel memories with family, I convinced myself to experience O‘ahu solo. While I had been there once before and was comforted by the promise of familiarity, the prospect of traveling by myself for the first time brought inexplicable feelings of hopefulness.

Even before I left, I noticed the deep intentionality behind my trip. Every item in my carry-on served me as a solo traveler: noise-canceling headphones, a power bank, my favorite thermos, and snacks. Each item was like a quiet declaration of self-reliance, but I couldn’t have predicted how much this flight was preparing me for more than just travel until I touched down.

Setting out solo and settling into O‘ahu

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There’s an old saying: “Go where you are welcome.” The Outrigger Reef Waikiki Beach Resort in Honolulu knew exactly what I needed, garlanding me with a luxurious Olomana lei of densely packed white and purple orchids reserved for special guests. It helps that the resort is located in the heart of Waikīkī, where anything I could have wanted, from pizza to entertainment, was nearby if not already on site. In my ocean-view suite, with multiple balconies opening to the salt air, one deep breath melted my physical fatigue.

Refreshed, I decided to meet Luana Maitland, or Aunty Luana, the cultural director of the resort’s A’o Cultural Center, located near the MonkeyPod Kitchen. There, guests get a hands-on education in O‘ahu’s traditional arts and crafts, such as lei-making, block-printing, hula dancing, and ukulele playing. Surrounded by beautiful heirlooms, Aunty Luana shared how significant these practices are to uphold and pass down.

“Our ancestors’ stories and their traditions are a gift,” she said. “By sharing their stories and traditions, we keep them alive.”

Aunty Luana’s story of single-minded perseverance in establishing the cultural center reminded me that courage can come from solitude, and that strength can be found in purpose. Her words rooted me more deeply in place and intention for the rest of my trip.

The next morning, over a leisurely breakfast at the Outrigger Reef’s Voyager 47 Club Lounge, I watched paddle boats take to the ocean. Diamond Head State Monument stood guard in the distance. I scanned the ocean for migrating whales, but resort staff later shared that the migration would be more pronounced in January or later.

During my own haku lei-making lesson at A’o, where I learned to make a traditional Hawaiian flower crown, I was reminded of the significance of being in tune with nature and honoring the land, its creatures, and caretakers. Nature has always been my anchor, and being solo on this trip meant I could listen to my own needs and rhythms without feeling rushed.

Experiencing the island through its culture-keepers

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The restlessness I had been feeling before traveling to Hawaiʻi had stemmed from losing legacies. O‘ahu was going to teach me how continuity is held and passed along.

Honolulu and Waikīkī are home to innovative culture-keepers. Farmers and fishermen share their bounty at restaurants like Merriman’s. Lithe storytellers incorporate hula into Cirque du Soleil’s mesmerizing ‘Auana performance, which centers on Hawaiian heritage and debuted at the Outrigger Waikiki Beachcomber Hotel in late 2024 (‘auana translates to “wander”). Elsewhere, chocolate makers pursue restorative farming and use vintage machines in a historic theater to make the creamy Lonohana Estate Chocolate. Each of these figures bridges the past and present in meaningful ways.

Other legacies are honored on O‘ahu, too. At Istanbul Hawai’i, a restaurant about a 10-minute drive up the road from Outrigger Reef, a mother-daughter team showcases modern Anatolian cuisine using local ingredients. Dining there, I wanted to linger lazily and let the warm, smoky flavors of my meal dance the halay (the national dance of Türkiye) on my tongue. The restaurant’s extensive menu made me momentarily miss loved ones, but dining alone meant savoring every bite slowly and recognizing the forgotten luxury of being present for myself.

Exploring beyond Waikīkī

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​Eager to discover more of the island, I took the Pali Highway (Route 61), which links Honolulu to the communities along O‘ahu’s eastern coast, toward the North Shore. Past the Nuʻuanu Pali Tunnels, the landscape transforms into a soft countryside. Flanked by tall cliffs peeking through the clouds on one side and the ocean on the other, the windward Kamehameha Highway (Route 83) weaves through a slower coastal suburbia dotted with green fields. At times, the horizon appeared to dissolve into the ocean, as though the sky and ocean were one continuous entity.

The farther I drove, the more I recognized the beauty of living in harmony with nature and with each other. At Kualoa Ranch, a 4,000-acre private nature reserve and filming location for countless films and TV shows, I revisited the emotional rollercoaster that is watching unforgettable movies: the feeling of sweaty palms during Jurassic Park, the nervous thrill of experiencing Jumanji or the series Lost, and the recurring heartbreak of 50 First Dates. I stood by the “Wall of Fame” to snap a cheeky photo and later pretended to be chased by a dinosaur.

Kualoa Ranch is a place whose potential is limited only by one’s imagination and perspective. I looked out over the treetops and scanned the ocean again for any signs of whales but spotted none. An odd, old song, Looking for Whales by A-ha, came to mind. I chuckled. Like its cryptic lyrics, I had indeed been looking for them, and me.

Slowing down on the North Shore

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The day-long drizzle had soaked through my sneakers, and I was grateful that my next hotel, Courtyard by Marriott Oahu North Shore, was nearby. As I slurped my dinner of grilled cheese and soup, the airy, local-art-filled lobby blossomed into a community space: families gathered over board games, a lively pop-up market buzzed with customers, and local talent entertained elders as they socialized. ​

The hotel is steps away from the ocean. Marked by a bus stop, a walkway between two houses led me directly to ʻŌnini Beach the next morning. The ocean was calm, but the beach felt plain at first. It didn’t feel crowded, but sunrise seekers and budding influencers had already found their favorite spots before dawn. I was unprepared for this shellless beach to pack such a powerful punch at the crack of dawn.

The moment the sun peeked over the horizon, it set the waters ablaze, and I was mesmerized. I felt the waves rush to kiss my feet as though offering a cleanse, each fresh wave erasing a million layers of emotional fatigue. I unconsciously fell into meditation, acknowledging the many difficult goodbyes I had said this past year and remembering travel-loving elders who had never witnessed this kind of magnificence. ​

With gratitude, I returned to sit beside Aunty Kela, a culture keeper at Marriott, who offered to teach me how she wove a tī-leaf lei and lauhala bracelet from the leaves of the hala tree using coconut oil, gifted by her Fijian cousins. We bonded over weaving tī leaves and bougainvillea flowers and sharing stories of grandmas and elders who instilled a respect for our heritage. Aunty Luana and Aunty Kela offered more than a lesson in local arts and crafts. Our intimate, unhurried conversations deepened as we worked with our hands, each movement weaving into my spirit and soul a profound reverence for personal journeys.

Finding perspective on my own

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The ocean called me back the next morning. I couldn’t miss one last ocean sunrise before my return. It was the morning of the winter solstice. I found a makeshift swing constructed from a palm tree log and settled to let it all rejuvenate me once more.

With deep breaths, I acknowledged the shift taking place: from here on, the days would only grow longer. I had traveled slowly but come the farthest. Saying yes to this journey — alone — had been an act of bravery. This wasn’t a chapter closing but a threshold. I was at the cusp of new beginnings, where I was to honor the past and welcome new chapters with hope and joy. I was to carry all good memories, stories, traditions, and values forward for myself, my daughter, and the family she would have in the future.

In the solitude of traveling alone on this beautiful island, slowly and intentionally, even though I had not seen whales, I felt I had just awakened the spirit of mine.