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In Hawaii, Things Keep Getting Better and Better

We joined my brother, his wife, and their then-eight month old daughter on an ambitious Hawaii adventure in 2018. They’d been three time—including their honeymoon—and declared it their favorite place on earth, so we knew we’d eventually tag along on one of their trips. They live in Oceanside, California, so Hawaii is a logical tropical getaway for them. My wife and I, from Boston, not so logical for us. But I’ve been visiting them out in California for the last decade, at least a couple times a year, so it was time to get ambitious and string together a California visit with Hawaii.


The trip involved two islands, Oahu and The Big Island. The Big Island was at the mercy of destructive volcanic eruptions, if you remember, so we felt uncertain what that half of the trip would have in store. But for now, we had Oahu.


Oahu is, of course, beautiful. That right there could be one of the stupidest and obvious sentences every put to paper, right up there with “pizza is good” and “I love to laugh.” So, anyway, yes, Oahu is beautiful.


Our first nights were spent in Waikiki on the outskirts of Honolulu, and while the beach was lovely and the surrounding green hills framed the town in a stunning and dramatic Jurassic Park-style scenery, I couldn’t quite shake the feeling that there was something a little, say, South Beach Miami about the stretch of hotels, restaurants, and high-end shops that lined Kalakaua Avenue. Maybe Las Vegas Boulevard might have been a closer touchstone. Of course, being pretty well-traveled at this point, I know that a lot of touristy destinations have boulevards like this: stretches that draw throngs of tourists but lack the true charm of what you came to experience. As much as I love Paris, the Champs-Elysees is not ideally the stretch you want to spend a large amount of time exploring. That doesn’t mean skip it. To me, it means see it, experience it, but be abbreviated about it. Know that you are in a neighborhood designed almost exclusively for the tourists. And then move on.


The next day we hiked Diamond Head, an 800-foot volcanic cone just south of Waikiki. The path to the summit is paved and makes for an easy trek with a spectacular payoff—the panorama of the Pacific and the beaches just north. Just a few miles apart, the peak of Diamond Head and the rush and dazzle of Waikiki Beach could not have felt more distant.

The fresh air and altitude helped me shake off the heavy fog of jet lag from the six-hour time zone shift from Boston. The greenery and blue sky and swath of ocean cleansed Kalakaua Avenue from my bloodstream, and Hawaii was beginning to take hold. Afterwards, we headed to a beach in Lanikai where my brother and I were able to sneak off and get some snorkeling in.


We had dinner and drinks on Tiki’s outdoor patio, live music playing, guests dancing while servers navigated around them. The food was good and the evening air warm and clean, an explosive sunset drawing everyone’s attention like a magnet. My niece, Anna, laughed and jumped up and down on our laps, each of us taking turns with her.


The next day, my wife and sister-in-law spread a blanket on the green grass in front of Waikiki Beach and played with Anna. I slept in, tired from the previous day’s hike. Later, after a swim, we met up for lunch and my wife was asked to be Anna’s godmother. I may have teared up, not just because of this moment but everything—the beauty of the scenery, the tropical and healthy vibes riding the air like radio waves, and of course this sense of love and family and unity, all coming together in a perfect storm. Sometimes you don’t realize a moment’s importance, a trip’s importance, whatever it might be, until long after it’s passed.


But sometimes you do.


We spent the afternoon visiting the Pearl Harbor Memorial, adding weight and importance and meaning to an already big day. Early the next morning, the five of us packed the rental car and we drove along the eastern coast of Oahu to the North Shore, where we’d spend the next several nights sharing a two-bedroom condo on the property of the Turtle Bay Resort. The long flights, Waikiki, jet lag, all truly behind me now. I felt rested, full of fresh air, my legs stretched on that hike a couple days before. I had some freshly-grilled corn on the cob in my belly after a detour to a community of gathered food trucks. Vacation was in full swing. My classroom, where just days ago I’d signed some yearbooks and told students to have a great summer, at last seemed like a lifetime ago.


We spent the next days hiking and swimming during the day, rippling palm trees, horse stables, the roiling ocean surrounding us. We watched surfers and climbed rocks. Took turns making Anna laugh. They’d filmed the movie Forgetting Sarah Marshall on these grounds, and it was easy to recognize the locations. At night we made dinner: ono fish, chicken, steak, and salad, and, after Anna was asleep, we had drinks and talked long into the night and played Bananagrams, a travel staple of ours. Then my wife and sister-in-law turned in and Jeff and I poured another drink and talked more, my head buzzing with bourbon and the salty scent of the Pacific Ocean, somewhere out there in the dark. I felt tired, but a good tired, a relaxed tired, one borne of sunshine and exercise and the adrenaline-surge of laughter.


A few days later we drove back south toward the airport in Honolulu to catch our puddle-jumper flight to the Big Island, where we’d spend the final days of the adventure. We pit-stopped in a small town to stretch our legs before the flight and finally partake in a shaved ice, Hawaii’s famous own. Christine ordered a “Matsumoto’s,” lemon, coconut, and pineapple shaved ice over a heap of vanilla ice cream. Two simple treats that somehow equaled something greater than their individual parts. We made another detour to Leonard’s in Honolulu so I could buy a couple malasadas—a Hawaiian treat of powdered sugar fried dough balls—another example of simple perfection. I was relieved to have the bag in my hand: I’d spent nearly the entire drive panicked that we wouldn’t have time to stop and I’d have to leave the island without them.


In Waikiki, we’d stayed in two separate hotels a few blocks from one another. On the North Shore, we shared a two-bedroom condo. In Kona on the Big Island, we each had our own condo unit in the same building, just a few steps from each other. The best of both worlds.

My wife and I fell in love with Kona right away. It’s a cute town, stitched on the shore of the Pacific, a long string of family-owned shops, galleries, restaurants, bars, most with outdoor seating in the cool sand, live music humming everywhere, white lights drooping overhead like plunging necklaces. Kona was much quainter than Honolulu, not quite as remote as the North Shore of Oahu. It reminded us a little of some of the towns in the Caribbean, or maybe a calmer version of Key West. In any case, we loved it. Christine wrote in her travel journal, “I may never leave.”


We’d been concerned for much of the trip about this leg of the journey, and in fact had been worried for weeks leading up to the trip: the Big Island was at the mercy of a once-in-a-millennium volcanic eruption. Parts of the island were closed off and unsafe. We’d wondered if we’d have to cancel this stop altogether. But, to our relief, the volcanic eruption seemed to be somewhat in check. While it had done incredible damage over the previous weeks, word was the devastation was waning. We were happy to be there, happy to give the locals much needed tourist dollars. Aside from a prevalent “vog,” volcanic fog, that lingered on the horizon, the impact on this side of the island seemed minimal.


Both condo units looked out at the water from just a few feet away. Jeff and Pauline had stayed here before, in the unit Christine and I had. This time, my brother and sister-in-law took the place one unit closer to the water with a wraparound balcony. In the mornings, we each had breakfast on our balconies, feeling the early sun on our faces, saying good morning to each other from our neighboring decks.


One afternoon Christine and I took a drive north to Blue Hawaiian Helicopter Tours for some sightseeing from the skies. We flew over arid lava deserts, everything brown and beige, and then suddenly, like a magic trick, we found ourselves over an expanse of lush green hills and mountains. The copter banked left into a striking valley between two peaks. Massive waterfalls plunged from epic heights. Christine got teary. I snapped photos, knowing as I did that my attempt to capture the moment was futile, like the times in my youth when I’d eagerly catch fireflies in a jar, only to have their magical glowing muted, until all I had was a jar full of bugs. Eventually I lowered the camera to my lap and leaned into her, her tears contagious.


Later, we joined Jeff, Pauline, and Anna on their balcony for drinks and a beautiful sunset, the dark orange sun seeping into the Pacific’s horizon line, then vanishing behind a strip of vog. We knew we’d be unable to articulate the experience we’d had on our tour, but Jeff and Pauline had taken a similar ride a few years earlier on a visit to Kauai, so we didn’t have to. Jeff cracked me a beer and handed it to me, then offered a silent toast and a nod of understanding. We clinked cans. That was enough.


The next day we headed out early for kayaking and snorkeling. Black and ancient volcanic rock plastered the landscape everywhere we went, beautiful in its own right, like otherworldly gems. We kayaked to a stunning cove and found ourselves surrounded by dolphins, their curved and smooth backs rolling from the water just out of reach. Dolphins glided beneath our kayaks, then disappeared. In the distance, we spotted another group of them, a pack of small, dark dorsal fins moving in unison. Then another group. Soon they were all around us again. I pulled my paddle out of the water and rested it on my lap, happy to pause and greet our visitors. Suddenly one breached the sea like a torpedo, up and straight out of the water, spinning then splashing dramatically back under the surface again. I blinked in disbelief, looking around for Christine, then Jeff, anyone to act as witness to what had just happened. But they were far ahead and facing the other direction. The moment had been mine alone.


That evening we took a boat excursion out to sea for some night diving in hopes of seeing giant manta rays. While the rays remained elusive, the trip was worthwhile and fun and full of nervous energy, as neither Christine nor I had night dived before, the underwater landscape dark and impenetrable, the silence even more prevalent than during the daylight, the isolation enhanced. Just the prospect of a giant manta ray arriving from the vacuous dark and cruising by us kept our bodies warm and buzzing with adrenaline, long after we’d returned to land.


In the morning, Jeff and I snorkeled from the rocks near shore, then spent a final leisurely day enjoying Kona and each other’s company. We played some more with Anna and took a walk to watch some of the Fourth of July parade. We took a ride to a hidden cove called “End of the World” and watched Jeff cliff-jump into a roiling bath of seawater. He’s never found an oceanside cliff that he didn’t want to jump off of. In the distance, goats hobbled around the volcanic rock, looking at us with curiosity.


On the way back, we stopped for avocado and tuna poke bowls and ate outdoors, letting Anna entertain us. The trip felt like it was winding down, leaving me feeling good and satisfied but also melancholy. I focused on Anna and her infectious laugh and energy.


Back on the balcony, we put out a snack spread of cheese, pepperoni, and crackers. We fixed ourselves final-night drinks and toasted the great trip, its meaningfulness already revealed to us all, no time and distance for reflection needed. Then, the night sky a dark canvas, Fourth of July fireworks began out over the water, vibrant and alive. Rain of colorful light painted the sky and mirrored on the dark sea. To our right, the scalloped curve of downtown Kona danced with torchlight. We sat back and drank and ate, our feet up on the railing, a feeling washing over me that I realized was appreciation.


Our conversation quieted as the fireworks kicked into another gear. I thought about Goldilocks, of all things, how she’d tried three of everything: beds, porridge, whatever else. Honolulu was a nice introduction, if not a little too busy and commercial. North Shore had been a welcome respite, remote and decompressing, the nights silent, reminding you of your isolation. I enjoyed it thoroughly and was concerned about leaving it for something else. But I needn’t have worried. The fireworks popped overhead, the town twinkled, the sound of waves lapped the shore. I looked sidelong at my wife and sister-in-law, at my brother, but they were engaged in the spectacle overhead. I sipped my beer, watched them a moment longer, then turned my gaze back to the sky. Kona, and this night, were just right.



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