Maui — One-Year Update

Trey Whitaker
11 min readAug 7, 2023


Sunset from Makena on the island of Maui

One year and 5,000 miles.

Given everything that has transpired, it feels longer and further. In fact, the past few years seem more like a decade.

2019 included two CrossFit Opens, Caylee’s college graduation, a trip to Paris, a Lyme disease infection and 60th birthdays for Cherry and myself.

I was determined to have a more peaceful 2020, but we all know how that went. Instead of chilling out, the year was spent scrambling to keep our CrossFit community together and the business solvent.

In 2021, we had plans to upgrade our Florida condo where we’d vacationed for nearly a decade. As it turned out, while we were planning our snowbird existence, Caylee took a new job and moved to Maui.

Therefore, 2022 took us in a very different direction. We sold our business, our home in Connecticut and our condo in Florida to purchase a place on Maui. We gave away or sold 98% of our possessions including my Jeep. We then shipped a car and our few remaining belongings to an island in the middle of the Pacific. After a drive across the country and a flight over the ocean, we finally reunited in Hawaii.

In a nutshell, that’s how it started. So, how is it going?

Sliding Sands Trail at Haleakala National Park

Doing what you prefer versus what you’re required:

Since becoming a paperboy in middle school, I’d worked for about 50 years. It remains tempting to do something. Maybe just out of habit? Or maybe for fulfillment?

When I first arrived, I checked the job boards and found that there were lots of part-time jobs. I applied for a couple roles, but decided it was too soon.

Instead, I took on three volunteer roles. One of these was at Haleakala National Park. They recently had openings for full-time Park Rangers, but I declined since the drive is more than an hour each way. Tack that drive onto ten-hour work days and it felt like too much. It was very tempting and I still think about the adventures I’m missing out on.

More recently, I applied for and was offered a part-time job at the nearby post office. Apparently, for myself, not working is harder than it might seem.

At this point, I’m still only volunteering my time. I really enjoy my roles as a trail steward at the park, doing groundskeeping at the Sugar Museum and cleaning up beaches with the Pacific Whale Foundation. When I go to sleep before a volunteer day, I rest easy knowing that, if I choose to, I can skip the volunteer duties and go to the beach instead. That’s a lot less stressful than having to clock in for a real job.

Birthday photo at Aloha Kihei CrossFit

Saving oneself:

While I’m not the fittest dude on Earth, sports and exercise have always been a constant in my life. In early 2022, I was really feeling my physical decline. When hiking, I was choosing routes with lesser inclines and using a walking stick to push myself up the hills.

In the CrossFit Open, I’d dropped from 334th in 2021 to 1912th in 2022. My VO2 Max (cardio fitness) was 26.0/poor in 2022. This year, my last in the 60–64 year old age group, I moved back up to 889th and my VO2 Max is 36.8/good.

My goals for 2024? Try to qualify for the CrossFit Games quarterfinals in the 65+ age group and improve my VO2 max to 41.0/excellent.

The bottom-line is that life on the islands has turned my life around. I’m now trending in the right direction.

Abbey sunning herself in her yard


Sometime in the Spring of 2022, I lost my sense of smell. I didn’t realize it until I arrived in Hawaii and couldn’t smell the ocean or the flowers. It’s not a complete negative. Taking Abbey on her poop walks isn’t as fragrant as it would be otherwise.

These days, my smell makes random appearances. Without warning, I’ll sense a burst of flowery fragrance and realize that there’s a part of Maui that I’m missing out on.

Shoreline view in Wailea

Fantasy island:

We purchased a place in Maui without seeing it in person. We’d only seen Zillow photos and viewed the location via FaceTime. In the months that followed, I began imagining my life in Maui. When I arrived, it wasn’t exactly what I expected. I mean, how can anything measure up to one’s imagination?

There’s also a difference between vacationing somewhere and living there. On Maui, the weather is always pretty good and the only thing that changes are how many visitors are in the mix.

Last week, I was walking a trail and came across a visiting family of four. The father and son were leading the pack and the daughter was acting as a connector to the mom who trailed behind. The mother and I chatted briefly and I commented to her, “You guys have a beautiful day to hike on the crater.” She replied, “Everything is beautiful on this island.”

It was a good reminder that vacationers can see all that’s beautiful about Maui. Residents can sometimes overlook these blessings when witnessing the homelessness, the glut of visitors and the high price of living.

Is it paradise? In many ways, but it’s not unlike every city in the country and faces similar challenges.

I’ll say there’s one thing that I don’t miss whatsoever. You know those cold mornings when there’s a dusting of snow on the driveway? The ones where you step onto the driveway to brush the snowflakes off your windshield and slip on a unseen patch of ice? When you twist your body in unimaginable ways to avoid a massive concussion or a disabling broken hip? Yeah, I don’t miss that.

Sunset at Ocean Vodka in Kula

The conundrum of modern communications:

This has continued to be one of the hardest things for me to figure out.

During my days in the Army in the 70s and when I lived in Los Angeles in the 80s, there weren’t many long distance communication options. It really came down to letter writing or expensive long-distance calls.

This era has many affordable options and I’ve used a lot of them including social media, texting and video apps like Marco Polo.

The time difference is certainly a hurdle. I’m usually up by 6:30 AM, but that’s already lunch time on the East Coast. It’s similar to waking up at noon and staying up late every day. It’s almost like being a teenager again.

Typically, I have several texts and an in-box full of emails to catch up on over coffee. We usually eat dinner around 7:00 PM or later, but that’s 1:00 AM on the East Coast and only a couple night owls will respond to a text at that hour.

So it has come down to regularly communicating with a core group and then reaching out to others when I’m reminded of them or if I’m prompted by a social media update of note.

The bottom-line is that communication has changed a lot since the days when my mother rang a dinner bell to summon us from wherever we were getting into mischief in the neighborhood. We have a myriad of ways to communicate to all corners of the world, but how do we do that effectively?

Surfing in Kihei

An old car that’s badly in need of a tune-up and four new tires:

For a long stretch of my life, I would wake up and feel sore. It was a proud sore. I’d think back to a long run, tough basketball game or hours of wood chopping and be able to draw a straight line between cause and effect. Even as a kid, I was proud of my scrapes, bruises, stitches, splints and casts.

These days, I wake up every morning with some sort of mysterious muscle or joint ache. I often think about canceling my CrossFit class reservation or skipping my volunteer work. By the time Abbey and I are 10 minutes into our morning walk, my body has usually worked through the kinks or I’ve devised a workaround for the physical glitch.

Another consideration for older folks is mental acuity. A good friend and I do Wordle each day and share our results. Each evening, I do the New York Times mini Crossword and on Friday I take the weekly News Quiz.

On most days, I have been using a phone application called Elevate to test my writing, speaking, reading, math and memory. In the first four categories, I’m scoring 84, 87, 92 and 96. Memory? Only 57. Oddly, I can remember the line-up of the 1966 Baltimore Orioles, but my neighbor’s names remain a mystery to me. Well, something to work on. If I remember to.

Sunset cruise in Lahaina

I’ve been called Troy, Terry and Trent:

Based on parent’s calling out to their kids, it seems like half the young boys on Maui are named Kai. Walking around the farmer’s market, I often hear other cool names like River and Winsome. A couple weeks ago, I ran across a dude called Bonz Atron. Bonz advised me that he was a world champion in the sport of kendama. Not to be a skeptic, but I did Google him when I got home. He wasn’t fibbing.

All this has me thinking that I might need to update my name to something with more of an island vibe. Trey has actually become more popular in recent years, but it’s nowhere near as common as Kai or as cool as Bonz.

Maybe Keanu. It’s Hawaiian for ‘cool breeze’.

The Doobie Brothers performing at the Maui Arts & Cultural Center

Please do well:

In recent months, we’ve continued to see bands coming through the local venue on their 50th anniversary tours. I find myself feeling anxious for them. Most of these performers from my youth are in their seventies and I worry that they won’t be able to live up to their glory years.

Luckily, the past two groups, America and The Doobie Brothers, were excellent. Their musicianship is still top notch and they bolster their performance by including a group of younger voices to keep things fresh.

Snorkeling with Dino at Molokini

So many visitors:

The local population on Maui is about 154,000. The average number of visitors is 66,500. That’s 43% of the local population.

With the massive amount of vacationers, the residents are accustomed to differentiating between the two groups.

I often ride my bike past a gentlemen who sells large wood carvings made from a local wood called monkeypod. One day, I stopped and asked him about a particular design. He said that the price would be $8,000. After we spoke for a while, he realized that I wasn’t a vacationer and lowered the offer to $5,000. These ‘kama’aina’ discounts are typical on the islands. (Note: $5,000 was still too steep for me.)

I’ve become more proficient at understanding who’s here for a short stay. Abbey and I often witness vacation runners on their early morning jogs as they glance around uncertain about their route. We see visiting girl gangs amazed by coconuts that have washed ashore. Newlywed couples with matching floral outfits and copious amounts of selfie gear.

Recently, as I was walking up the trail at Haleakala, I witnessed a young blonde woman quickly skipping down the trail wearing a flowery headband, a glittery tube top, a long pink skirt and flip-flops. I hope that turned out okay.

It is suggested that Maui is a place for vacationers to know their limitations versus testing their limitations. Far too many visitors find themselves needing to be rescued from the ocean or mountain trails.

We’ve also been lucky to see several friends from the mainland. We’ve shared the crater and the ocean without incident. No sharks; just turtles. No volcanic eruptions; just hiking. Plus plenty of food trucks and restaurants.

Caylee and Cherry in the Philippines

Family life:

Being on the island for a year has allowed all of us to find our routines.

Caylee zooms between her full-time work, her part-time gig, outings with friends, Zumba with Cherry, CrossFit with me, and squeezes in time at the beach.

Cherry is adjusting to retirement by not waking up at 4:00 AM anymore and doing volunteer work at her church. In the past couple weeks, she has probably watched more World Cup soccer than most TV pundits.

Abbey just turned 9 years old and is still enjoying her morning and evening walks to the beach plus a couple visits to the gym each week. In her yard, she suns herself and chases away the lizards.

The thing I appreciate most is that we can share dinner a few times a week. This past Friday, as the sun was setting over the nearby beach, we went to a local gathering of food trucks to eat tacos and sip boba tea as folks danced along to the music of a local guitar tandem.

We miss our friends and family dearly, but having each other’s company is precious and priceless.


Time to write:

In recent months, I’ve spent hours upon hours considering and reconsidering a storyline for a fictional story called ‘By Chance’. I’ve finally arrived at a point where the storyline feels complete and the writing can begin.

I’ve collected my notes and research into a single tool called Living Writer. This includes AI-generated reference images of the story’s characters. The character ‘Lucy’ is pictured above

The story is set in the mid-1970s when I was in high school. To set the mood while writing, I’ve created a playlist with many of my favorite songs of the era. The playlist link is below.

Link: Writing Music for ‘By Chance’

Dinner with a view

The kindness of others:

In the past year or so, I’ve seen many friends relocate. Roaming the country in an RV. Graduating from college and starting lifes in different states. Venturing off to build wilderness trails. Selling a home and business to live beside the mountains in Wyoming. Uprooting to attend graduate school in Idaho. Becoming a travel nurse and living in a new city every few months. Even moving to England to attend the University of Oxford. So many folks doing brave and amazing things.

There’s quite a few of us who find ourselves far away from our friends and family and, at times, it can be a little unsettling.

While we’re all building new networks and communities, it’s still heartwarming to receive a call, a text or see a nice comment online. We appreciate the home team keeping us in their thoughts.

Sacred Garden in Haiku on Maui

With our second year underway, I’m going to leave the periodic updates behind to focus on writing ‘By Chance’, spending time with visiting friends and taking care of myself and my awesome crew.

Be well, take care and I hope to see you soon.



Trey Whitaker

Former CrossFit gym owner, corporate manager, paratrooper, youth sports coach and jujitsu black belt. Now a trail steward at Haleakala National Park on Maui.