Traveling to Hawaii Is Really Complicated Right Now. Here’s How I Did It

Thirty-six hours. That’s how much time I had before my flight out of New York City, final destination Maui, when I received a text message about my COVID test results.

Insufficient specimen.

“Insufficient specimen!” I repeated, in an increasingly panicked tone, as I tore into the bedroom where my husband was packing for the big birthday trip. My big birthday trip.


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“I can’t tell if you’re joking,” my husband, Steve, said both because it is a thing we do with one another and also because his test results had come back negative only an hour earlier. There was no way this person I shared spit with didn’t have the virus but I did.

Once Steve realized I had never been so serious, he calmly told me not to freak out even as I proceeded to do exactly that.

Negative and Approved Tourists

The trip was over before it started. The state of Hawaii had made itself abundantly clear: Produce a negative COVID-19 test result within 72 hours of departure or prepare to quarantine. Oh, but not just any COVID test. A Hawaii-approved partner.

These were listed on the state’s official website and updated frequently, along with all other COVID-era restrictions and protocols. Just one day earlier, I’d learned that Maui required a contact tracing app to be downloaded to all visitors’ phones before being allowed entry.

We’d opted for the American Airlines partner option, Let’s Get Checked, and before I’d even managed to get a representative on the phone to tell me what I already knew—there was no time for them to send me another test and get me my results—I was racing out the door to find the nearest HI-approved testing site that would prove I was negative (which I was luckily able to do).

Our journey to Maui’s Kahului Airport was seamless. As expected, when we deplaned, we were ushered into a line and asked for hard copies of our test results and QR codes. We had everything in order and were cleared to leave the airport.

Magical Maui

When we arrived at The Four Seasons Maui in Wailea on Maui’s South shore, I was ecstatic. We were just in time for sunset.

In spite of the COVID situation, the plan to travel around the island remained in place: First, we’d stay at The Four Seasons then head up to Paia for several nights before decamping at the adults-only Relais & Chateaux Hotel Wailea. If Steve was getting tired of my predilection for traveling like this, he knew enough not to make a fuss this time around.

I felt comfortable heading into our Four Seasons stay, but the attention to details throughout the property, perhaps most notable in our room, impressed me nonetheless.

“Welcome” gifts included a Lead With Care kit including masks, hand sanitizer, and wipes. The room itself contained HEPA air purifiers; a UV box for sanitizing small gadgets like the TV remote, keys, cell phones, etc. 

At the Serenity pool, we wore masks on trips to the restroom and on a walk down to the beach below.

Couples on babymoons, families on annual vacations, others desperate for a sun-kissed escape—we’d come for different reasons, but we’d all come to paradise.

Everyone seemed thrilled to be there. Early cocktails led to quick conversations with strangers about the lengths taken to get to the far-flung state. One man admitted to getting two COVID tests—just in case. Another person said she was tested at work every week but needed to get tested for the Maui vacation using one of the approved partners.

Couples on babymoons, families on annual vacations, others desperate for a sun-kissed escape—we’d come for different reasons, but we’d all come to paradise.

I’d fallen in love with Hawaii seven years ago—the Big Island and Kauai entranced me, but I was seeing Maui for the first time, and it exceeded my expectations. It was magical.

Beaches peppered with sea turtles; a crater you can hike (Haleakalā); lush country landscapes; goat farms and coffee farms; potent Mai Tais; pineapples sweet as brown sugar; Michelin-starred meals overlooking crashing waves; food truck plates devoured on a hot bench or in the cool of an air-conditioned car. Surfing, kayaking, stand-up paddleboarding—things you can surely find elsewhere but nowhere as magical and edifying as Maui. It’s a formidable task, trying to describe this place with its perfect weather and its beautiful, warm people.

Aloha or No?

With the exception of a few restaurant closures, temperature checks at the restaurants that were open, and face coverings in public, I didn’t find a COVID-compromised trip.

I found myself looking for signs that residents (and inconspicuous staff at restaurants, resorts, and the sailboat we took to Molokini Crater for snorkeling and boat lounging) were either angry or annoyed at our presence.

I’d heard as much and ended up forgoing a trip to Hana—the famous Road to Hana journey would have to wait until next time—after hearing one too many times that that remote Eastern part of the island wasn’t yet prepared to welcome tourists. My decision was further validated when Katie Horan, the guest services manager at Hotel Wailea, told me she was from Hana and that we were right not to go.

I experienced only one such encounter when someone made a gesture and said few choice words to me.

We would never forget we were living—and vacationing—during a pandemic. Steve and I still read the news every night, and we constantly double-checked that we had our masks before venturing out, but even this did nothing to deter the aloha spirit we found in every corner, in every interaction.

At Sea

Our skipper and his two-person team for Sail Maui explained it was imperative we wear our masks when leaving and entering the harbor but was a bit more relaxed about the requirement after that. Don Prestage with Sail Maui said they’d reduced numbers on the boat tours, adding that they “always preferred the more personal feel and interactions of lower passenger counts, so keeping the numbers low was nothing new to us!”

Every individual party on the boat kept to themselves initially, but once we got going, we found ourselves mingling and exchanging snorkel stories and restaurant recommendations, careful not to get too physically close to one another.

It was humpback whale season, and our group got inundated with sightings…Finally, something COVID could not hurt.

Every so often, one of the boat’s passengers or crew members would shout, “Whale’s tail!” and point excitedly.  It was humpback whale season, and our group got inundated with sightings. “Like clockwork, they arrived this winter for their annual mating season and their numbers have only been increasing,” Prestage said when I followed up with him later. Finally, something COVID could not hurt.

Plan B

I turned 40 on January 29, our second-to-last day on the island. In the morning, I drove out to Kalama Park and Cove Bay for a surf lesson. Out on the water, while we waited for the right waves (my instructor providing endless entertaining analogies on waves and dating), I went over the moves he’d taught me in my head but mostly I just looked around gratefully from my perch on the board. This wasn’t the South African safari I’d been planning pre-pandemic for my milestone birthday, but it hardly felt like a Plan B.

After the lesson, I met Steve by the pool and proceeded to drink fruity cocktails that, in the very capable hands of James Shoemaker, Hotel Wailea’s principal bartender, also managed to be refined.

Later over snacks (and more drinks) in Hotel Wailea’s Birdcage, where the green and pink lovebirds sat adorably in pairs on the beams above us, I researched the hike to La Perouse Bay I would take on our last morning.

I didn’t want to leave, but I wasn’t fixated on how much time we had left, something I’m guilty of doing while traveling. This time instead of counting down the days left and growing depressed, I lived in the moment. I loved every precious minute.

Perhaps I’d learned something from my 10-month travel hiatus. Either that or I was simply older and wiser.

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