Hawaii holds a special place in my heart. As a child, I dreamed about visiting the exotic island-state, but alas, my family vacations always centered around a visit “back east” to see family or a trip to a national park (I now realize that I was extremely lucky to get to visit such incredible places as Yosemite, the Grand Canyon, and Yellowstone when I was a kid).

Once I began my professional career in San Francisco and finally started earning enough to think about planning a vacation on my own, Hawaii was of course on the top of the list. In my late twenties and early thirties, it became an annual tradition to escape winter and visit at least one of the islands with whatever guy I was dating at the time. Now I am embarrassed by how unimaginative my vacation plans were year in and year out, but Hawaii was an easy destination when all I wanted was a week on a beautiful beach with the sun on my face.

Then I moved to New York for work in 2014 and my annual trips to Hawaii became a thing of the past. Suddenly, it was much quicker to reach the Caribbean if I wanted a beach vacation. Hell, it was easier to fly to Europe than it was to get to Hawaii from NYC. My leisure travel plans began to look a lot more diverse.

Fast forward to November 2019. After three weeks in Asia (Singapore, Maldives, Vietnam, Philippines, and Japan), I needed to get to the west coast for Thanksgiving. Yes, I could have flown nonstop from Tokyo to San Francisco or Seattle, but a brief stop in Hawaii sounded a lot more fun. It would break up the long flight and I’d get to return to one of my favorite places in the world. Win-win.

Bonus Day on Oahu

My travel day to Hawaii started with me waking up in Tokyo and thinking about the logistics ahead. Taxi to Shinjuku Station, Narita Express to Narita airport, seven hour overnight flight to Honolulu. Upon landing the next morning, I’d clear immigration, get my luggage, board the short flight to Kauai, then get my rental car and drive to the north shore of the island. Except… if the flight was seven hours long, how would I be landing in Hawaii the next day, when Honolulu was in a timezone nineteen hours behind Tokyo’s?

Ohhhhhhhh, duh. I’d be crossing the international date line, so instead of landing on Tuesday, I’d land on Monday, on the same morning of the evening I had taken off in Tokyo. I had a 43 hour Monday ahead of me. Is that a mind trip or what? I’d crossed the international date line many times before, but never in such a dramatic fashion; usually I spent the majority of my “extra” day in transit. Now I had a full extra day and night in Hawaii that I hadn’t bargained for.

Since my flight, rental car, and hotel in Kauai were all booked for Tuesday, I figured the easiest thing to do would be to leave everything as is, and book a last minute hotel in Oahu for my bonus day. Having visited the concrete jungle of Honolulu and Waikiki Beach several times in the past, I opted to stay at the Four Seasons Resort at Ko Olina, on the west coast of the island, and removed from all the urban action.

View from the adult pool at the Four Seasons Ko Olina
My room featured a balcony with a view of the ocean and the rugged mountains in the distance

Since I only had a day on the island and was fighting jet lag, I decided it was okay to not be too ambitious with my bonus day. I was living through a 43 hour Monday; wasn’t that enough? My big plans were: gym, pool, walk along the path that connects all the developments in Ko Olina, happy hour, dinner, and bed.

Ah, I had missed Hawaiian sunsets
Dinner was at Noe, the Italian restaurant onsite that described its menu as “Capri-by-way-of-Oahu”

As I waited for my Uber to arrive the next morning (Uber’s expansion to Hawaii was a welcome development since my last visit), I reflected on my quick visit. The amenities and facilities at the Four Seasons had been quite nice, but the room felt a bit dated, and the hotel itself was larger than what I prefer these days. However, the staff had all been friendly and warm, exuding the happy Aloha spirit. People took their time to chat with me, and they seemed to genuinely want to engage. The bellhop told me that he had family in New Zealand whom he visited every year, so we discussed New Zealand and my upcoming trip there for about five minutes. With a lot more travel experience under my belt, I had a new appreciation for Hawaiian hospitality.

Flying over Oahu en route to Kauai to begin the part of the trip I had actually planned.

My Conflicted Decision to Return to Princeville

The first time I visited Kauai in 2010, I stayed at the St. Regis Princeville (coincidentally featured in the George Clooney film The Descendants in 2011) with my (now ex) boyfriend. It was also my first time staying at a St. Regis hotel, and I instantly fell in love with the unique property and its dramatic views overlooking Hanalei Bay. The five glorious days coalesced into one of my favorite vacations to date, circa 2011. When I returned in 2013 (new boyfriend in tow), the building was continuing to show its age, but the magic still remained. Looking back, I partially blame the St. Regis Princeville for sparking my passion for luxury hotels. It couldn’t help either of the aforementioned relationships; I ultimately ended them both, but my obsession with high-end travel had just begun.

Imagine my consternation when I learned that the St. Regis was being sold to a new owner in 2018, and that the property would be re-branded as The Princeville Resort (to be fair, it had actually been opened under that name in 1986, then renovated and re-branded as a St. Regis in 2009). Interestingly, the new owner, Starwood Capital, was founded by the same guy who founded Starwood Hotels & Resorts.

When I was planning my return to Princeville in 2019, there was plenty of speculation that the property would undergo a complete renovation and eventually re-open as a 1 Hotel (one of Starwood Capital’s holdings), but nothing had been announced yet. In the meantime, reviews claimed that management was essentially letting the property go until its impending makeover. Repairs weren’t being made and old, fraying linens weren’t being replaced. I struggled deciding whether to stay at The Princeville Resort under these conditions; however, the surrounding area really doesn’t offer great alternatives, and the views and location couldn’t be beat. I ultimately opted to take my chances.

View of Hanalei Bay from my room – can you see how I fell in love with this place?
Another view at sunset
One more at dusk – the view really does not get old

Deciding Whether to Hike the Kalalau Trail or Not

I did not have many big plans for my stay in Kauai; I had been to the island several times previously and had already experienced many of the attractions. The main goal was to relax and recharge before a big week visiting family and friends up and down the west coast.

However, I hoped to hike part of the Kalalau Trail along the Napali Coast on my one full day on the island. Notorious for rainy weather, the trail along the north shore is often quite muddy, and portions can get flooded in heavy rains, creating dangerous conditions. People have died trying to cross through flowing streams, getting swept out to sea; or when trying to pass along narrow, steep ledges, falling to craggy rocks below. Large groups of hikers have also been stranded overnight during flash floods.

The trail was closed for over a year in 2018-2019 after flooding incurred serious damage. It had now been re-opened, but a parking permit was required to visit the park, and limited numbers of permits were issued. By the time I realized I’d need a permit, the only ones available were for the 6:30am-12:30pm time slot. I went ahead and got the permit, but wasn’t sure I’d use it.

Upon checking in at the hotel, I chatted with the concierge about the trail to get his opinion on whether I should brave it alone. I had hiked part of the trail to the waterfall before, and it had been magnificent, but very muddy and difficult to follow after we passed the river and turned into the forest. The concierge didn’t exactly assuage my concerns; he told me that if I decided to do the hike, I should come see him afterwards and let him know I was okay. If he didn’t hear from me, he’d raise an alarm. Hmm, that didn’t inspire confidence. Plus, I’d need to wake up around 5am to get to the trailhead at 6:30am, and it would still be dark then. Did I really need to do this?

Nope, I didn’t. Instead, I spent part of the day at the pool, then drove into Hanalei to walk around and enjoy a late lunch. There was no need to take a risk to go on a hike by myself that I’d already done before, regardless of how beautiful it may have been.

While not the coast, the views overlooking the fields on the way to Hanalei were also gorgeous
One more angle

Final Day in Princeville

Since my flight out of Lihue wasn’t until almost 10pm on Thursday, I had most of the day to enjoy on the island. However, I wasn’t able to get a late check-out from the hotel, so I needed to plan accordingly. I decided to book an early afternoon facial at the spa so I could enjoy the gym and pool in the morning, check out, relax at the spa and shower before driving to the airport.

While I normally like to tune out at the spa and limit conversation to required topics (I.e. what are your skincare concerns? what kind of pressure do you want for your massage? do you have any allergies?), I found myself chatting with the aesthetician. I told her I was going home to the west coast for Thanksgiving and we realized that we had both grown up in Oregon. Southern Oregon, to be precise. She was a few years older than I was, so we hadn’t overlapped at school, but her father had been a teacher at my elementary school (not my teacher, but he was popular, so I oddly remembered his name). What an oddly small world.

After we discovered our weird connection, we became fast friends and she opened up to me about all of the controversy and uncertainty surrounding the hotel with its new ownership. Like much of the staff, she had been working there for many years, and felt uneasy seeing the deteriorating conditions of the property, especially as she welcomed back return guests who had been visiting regularly over the years. And of course, she worried about the security of her job. “They have told us that they plan a renovation, but they aren’t going to shut down completely,” she told me. “However, we doubt that they are going to be able to overhaul the place without closing temporarily.” It sounded like she had other opportunities on the island but was happy with her position and work family at the resort. I wished her luck as I bade her farewell; I didn’t want the wonderful long-standing employees to move on either.

After my relaxing (and surprisingly social) facial, it was time for me to say goodbye to Princeville for the foreseeable future. As I waited for the valet to be brought up, one of the bellhops out front started chatting with me. Tall and fit with shaggy hair, he was clearly a surfer living his best life on the north shore of Kauai. After making some small talk, he cut to the chase. “Were you staying here by yourself?” he asked me while smiling flirtatiously. “Yes, I was,” I told him. “Wow, really?” he responded. “That’s so brave of you.” His expression was genuinely intrigued.

HA! At that moment, my Jeep pulled up, so I didn’t have the chance to explain to the cute surfer/bellhop that visiting Kauai by myself was one of the least adventurous things I had done in the last nine months. Quitting my job and boarding a plane to Chile? That was scary. Visiting Egypt and Mozambique on my own? Very intimidating. Arriving in Beirut solo after a week in Israel? That felt brave (maybe even a little stupid). Hanging out at a resort in Kauai for a couple days? Piece of cake.

I had been worried that Hawaii might feel too easy and basic after recent travels had expanded my worldview exponentially, but the destination had maintained its special place in my heart.The mind-blowing natural beauty and genuine, easy-going hospitality of the islands still held up against some of my most spectacular travel experiences over the past few years.

Unsurprisingly, it was later announced that the 1 Hotel Hanalei is set to open in late 2021. I for one will be anxiously awaiting the opening and can’t wait to see the new property. I have no doubt that it will be stunningly beautiful, but my biggest hope is that the spirit and hospitality that made the St. Regis a special place will remain intact.