23 Days in Hawaii: Our Slow Travel Fail
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Living like a local for weeks at a time. That was the dream when I went part-time. Every day spent away would be sublime.
I promise the rest of this post won’t rhyme.
Our first lengthy family adventure was a complete success. The four of us spent three glorious weeks in Mexico. Our apartment overlooked the friendly and vibrant city of Guanajuato.
We woke up naturally to leisurely mornings. Our commute to school was a hike down the winding
alleyways stairways. We explored our city, attended Spanish classes together, made new friends, and even made a habit of journaling and attempted guided meditation, actually getting our boys (and me) to sit still for minutes at a time!
Our Slow Travel Fail
I spied a four-day CME conference on Hawaii’s Big Island. We had visited Hawaii a couple times, but had never been to the Big Island, and our boys had never set foot on a single Hawaiian isle, so we made plans to go as a family.
If you’re going to fly all that way and cross four time zones, you might as well stay a while if you can. And we can. I don’t work that much these days, and our boys’ school is lenient with our time away, so we planned a long trip. A 23-day long trip to be exact.
And if you’re going to fly all that way, and you have 23 days to spend there, you’ve got to visit multiple islands. We’d never been to Kauai either, and we had heard it was beautiful (it is), so we added that to the list. Oahu’s got a lot to see and do, especially for the kids, so we added Oahu to the itinerary.
We booked one night at a luxury hotel in Waikiki the evening we flew in. I had more than enough SPG points to book The Royal Hawaiian from the welcome bonus on a Starwood Preferred Guest American Express Card, and when we returned to Oahu, we stayed away from the hustle and bustle on the island’s west side.
The Big Island has a distinct division between the Kona side and the Hilo side, so we planned to spend at least a few days on each. And then we found a yurt in the south, not far from one of Earth’s four green sand beaches, so we booked a couple nights there, too.
Altogether, we stayed in six different places, rented three different cars on three different islands, which were reached with three different flights over 23 days.
So much for slow travel.
Our 23 Day Hawaiian Vacation
We might as well call it what it was. A vacation. We like to say we don’t take vacations anymore, but when you’re sightseeing all day, enjoying happy hour every evening, and never in one place long enough to unpack the suitcase, you’re on vacation.
We flew out of Minneapolis early on Super Bowl Sunday, just ahead of the next-day rush, catching much of the big game live from the semi-comfort of the coach seat on our connecting flight to Honolulu.
Uber took us to The Royal Hawaiian, a grand coral colored throwback of a hotel right on the shores of Waikiki Beach. After a restful night and an early morning wakeup due to the four-hour time difference, we played on the beach before catching our flight to Lihue, Kauai.
Not Slow Traveling on Kauai
Upon our arrival in Kauai, we picked up a sweet yellow convertible, crammed our gear into the little trunk, and headed off to the islands #1 most popular attraction: Costco. Honestly, I haven’t seen a retail store so crowded since the days when I actually partook in Black Friday sales at brick and mortar stores. Costco was similarly packed on the Big Island, but not so bad on Oahu.
With our provisions of food and beer to last a few days, we made our way up to Princeville, where our Airbnb ($40 off your first stay) apartment awaited us. It was actually a timeshare community at the Wyndham Bali Hai, which piqued my interest in this whole timeshare resale idea.
With just four days on the island, we kept busy, visiting waterfalls like Opaeka’a, gawking at the “Grand Caynon of Hawaii” a.ka. Waimea Canyon, driving through the tunnel of trees en route to the Spouting Horn blowhole, and of course exploring its many beaches.
One of those beaches, Ke’e Beach, was at the base of the Kalalau Trail along the Nāpali Coast. It was there that I randomly chatted up a family physician who, like me, attended medical school at the University of Minnesota. He had been retired since his mid-fifties and strongly encouraged me to live below my means to follow a similar path. Preaching to the choir, doc!
Another highlight on Kauai was the lighthouse and nature reserve at Kilauea Point. We watched whales breaching in the distance while albatrosses, frigate birds, and red-footed boobies soared just overhead. Having seen the blue-footed booby on the Galapagos Islands several years ago, we can now say we’ve seen both boobies.
Not Slow Traveling on the Big Island
Couldn’t hurt to stay in a yurt, am I right? Our first two nights were spend in a yurt high above the sea in an area appropriately named Ocean View. We also had a great sky view in this dimly lit, off-the-grid neighborhood. The boys loved our “glamping” experience, with one sleeping in the loft, one on the sofa, and my wife and I sharing the “master suite.”
We had solar electricity, propane-powered fireplace and hot water, and surprisingly reliable Wi-Fi, so I had no complaints, either. The terrain was other-worldly volcanic rock, as it is on much of the west and south of the island. Reminded me of Iceland. A very warm Iceland.
My CME fund footed the bill for our next four nights in a well-appointed condominium in Waikoloa Village north of Kona. I attended lectures while the rest of the family enjoyed time at the pool and the beach.
Speaking of beaches, we made our way down to Papakolea’s green sand beach at the southern tip of the island. We opted for the nearly six-mile round trip hike along the ocean, which was beautiful. The greenest sand, which comes from a volcanic rock called olivine, is actually found along the way, so if you hop in one of the trucks that will take you for $20, you’re missing out.
After the conference, we hit up the Hilo side, staying in a unique Japanese style home that was essentially a series of little buildings under one roof that wrapped around a center courtyard garden. You could call it a garden, but you could also call it a wildlife refuge; the hundreds of goldfish in the pond were occasionally dinner for the frogs, which were scared off by the chickens that ran under the house and into the inner refuge to raise a ruckus. As nightfall approached, all would seem calm until the shrill coqui frogs started hollering at the top of their little lungs.
The Winter Olympics were ongoing, and I did catch the men’s curling team capture the Gold Medal, but we mainly spent our evenings on the lanai enjoying good company (we were joined by a relative who flew all the way in from the mainland’s east coast), a cold beverage, and a good, loud show in the courtyard.
We also the pleasure of meeting up with a traveling troupe of physicians including Drs. Matt & Carrie Reynolds, the latter a pediatric gastroenterologist and the voice of The Hippocratic Hustle, the former a chill guy and surgeon.
Not Slow Traveling On Oahu
By the time we got to Oahu, winter breaks were in full swing on the mainland, so we had a bit more competition for affordable housing. We found a reasonable spot in the Makaha valley in a condominium complex that gave us an ocean view and an unexpected level of seclusion, being on the top floor overlooking the thick canopy of trees.
On the property grounds were a hot tub, pool, and an absurd number of peacocks. Dozens and dozens of peacocks. Have you seen any of the Minions movies? It was like that, but thick with peacocks.
I was proud of my boys, but what impressed me more were the volunteers and participants with Accessurf, who were out there giving the disabled and disadvantaged the opportunity to experience the joy of surfing.
We saw a young gal with a prosthetic leg surfing quite well; there was a wheelchair-bound man who caught waves on a larger tandem board with a lot of help from the volunteer crew. Nords let me know that it was one of his favorite charitable causes, and unbeknownst to him (at the time, at least), we decided to say Thank You for the lessons with a donation to Accessurf from our Donor Advised Fund.
Nords spent at least five hours giving private lessons to four of us; that’s worth $1,000 in my book, particularly when the money goes to a good cause.
Later that week, we returned to the same beach for a Bigger Pockets meetup with Brandon Turner, another graduate of The Nords School of Surfing. We were joined by Ty Roberts of Get Rick Quick’ish and CampFIRE Finance and his family of six, along with a couple dozen enthusiastic real estate investors. Great people and great food at the potluck picnic — I had my fill of delicious manapua and poke.
A few years ago, my wife and I hiked from the north shore out to Kaena point, the northwesternmost point on the island, to see the monk seals and nesting albatrosses. On this trip, we hiked to the same point from the western shore. We saw one monk seal (from 50+ feet away — it’s illegal to get closer) and the Laysan albatrosses had hatched, so we saw the fuzzy little chicks. I highly recommend the hike from either direction if you find yourself on Oahu.
Other highlights on Oahu include the Polynesian Cultural Center, a whale watching tour, the Dole Plantation — our boys loved the maze and we all loved the Dole Whip — and of course Pearl Harbor.
We flew to Hawaii for free. 3 round trips with travel rewards points, and one reimbursed from my CME fund.
Slow Travel versus Vacation
Slow Travel Ideal Morning: Wake up naturally, enjoy a home-cooked breakfast, and get a little schoolwork and blog work done before heading out for a few hours of family fun.
Actual Vacation Morning: The chickens started greeting the morning sun when it started rising in New York, we wake up to nature’s alarm clock and don’t bother showering since we’ll be covered in sunscreen, sand, and sweat in short order, and we head out for a full day of excitement, forgetting the sandwiches we had prepared the night before.
Slow Travel Ideal Afternoon: After a splendid three-mile hike in which we see the whales and dolphins frolicking off the coast under just the right mix of cloud cover, intermittent sun, and a cooling breeze off the ocean, we make it back to our abode and reflect on our day with gratitude.
Actual Vacation Afternoon: The rain altered our plans for the beach, mudslides have closed the nearby hiking trail, and we end up seeking shelter in a souvenir shop selling the same crappy tee shirts and shell-based kitsch you find at every tropical destination ever. We cruise home in bumper to bumper Hawaii traffic, arriving home to start making dinner about 30 minutes after the time we planned on eating dinner.
Slow Travel Ideal Evening: After dinner, we each read for an hour, the boys go to sleep without a fuss at 7:30 pm and maybe, just maybe, we enjoy an adult beverage or two together, but you don’t do that every night because this is not vacation. This is simply living away from home.
Actual Vacation Evening: “I said no Kindle if you can’t stop bickering, and you’ve been fighting since 11 a.m.!” The boys are finally ready for bed at 8:30 pm, and I crack the first of three strong beers because we’re only on this island for six nights and for some reason, I bought three six-packs on day one.
I may be over-exaggerating a tad, but throughout the trip, we realized we bit off a wee bit more than we wanted to chew. It’s awfully easy and rewarding to set up residence in a far-flung location for a few weeks and enjoy the surroundings at a slower pace. It’s also quite fun to take an extended vacation while bouncing from place to place, but these are two entirely different kinds of trips.
I’m glad we booked this one, and while our days and nights were pretty action-packed, we did partake in many memorable experiences in an exotic land chock-full of natural beauty. If we make it back to Hawaii as a family, and I imagine we will eventually, I would plan to spend several weeks on each island, rather than several weeks for the whole frenzied whirlwind trip.
Have you been to Hawaii? What was your most memorable experience? Any other slow travelers or slow-traveler-wannabes out there?
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