Maui — One Month Update

Trey Whitaker
5 min readAug 9, 2022


I’ve now been on Maui for nearly a month and have walked to the beach every day. That’s not a humble brag. The ocean is just unavoidable. It’s everywhere. It literally surrounds us. The ocean are so central to everyday life that I now have a phone app that tracks low and high tides.

Below are some thoughts about life on an island in the middle of the Pacific Ocean:

Beach Town: As a native New Englander, I’ve been lucky enough to spend time in beach towns like Kennebunkport, Provincetown and Charlestown. They all have similar looks to them. They’re a bit weathered by the sun, wind and tourists. Maui is a beach town, too. Not just from Memorial Day to Labor Day, but every day of the year. Beach towns have their charm, but they’re messy. Maui is a little messy.

Local Cred: Businesses will provide a ‘kamaaina’ discount to residents of Hawaii. For example, Foodland, one of the local supermarket chains, offers a discount to anyone with a Hawaii driver’s license. That ID and a decent tan provide instant cred. Another way to establish ‘local cred’ is by having a dog. Getting a pet to the island is a laborious and expensive process. Therefore, walking a dog is a sign that you’re a local. Abbey is often approached by vacationers who miss their canine best friends and need some affection. I’ve been thinking about having her wear a sign saying: ‘Dog Pets/$1.00’.

First Directions: A few evenings ago, as Abbey and I were walking along the beach, we saw a couple folks that appeared confused. I learned that they were a grandmother and granddaughter staying at a nearby condo. We guided them to a nearby path and pointed out the turtle pond down the beach. It felt pretty good to know enough to help.

Hawaiian Roots: In preparing for the move from Connecticut to Hawaii, I ran across a couple artifacts with ties to the islands. A photo postcard in my grandparent’s belongings indicated that we had relatives living on Oahu in the 1930’s. My grandparents also visited Maui in the 1970’s to celebrate their 50th wedding anniversary. As part of a high school trip, I visited Honolulu in 1976. Therefore, I’m nearly a native of the islands.

Dream Change: For the past couple years, my sleep has been filled with dreams with a similar theme. I would be in a building or a busy downtown area. I would be trying to get somewhere, but I would always run across impediments. Locked doors. Elevators that didn’t work. Blocked streets. Despite frantic efforts, my attempts were always frustrated and fruitless. Without fail, I would wake-up when I was still short of my destination.

With the move, I’ve found that my dreams have changed. There are no more endless and unsuccessful pursuits. The newest dream theme is solving puzzles. Trying to find a missing piece or putting them in proper order.

My guess is that the old dreams were about retirement and reaching my current destination. As for the newer dreams, I believe they’re about trying to find purpose and structure in this new world.

Fitness: According to the stats my Apple Watch is gathering, I’m now getting more than twice as much exercise. Between walks with Abbey, CrossFit and bike riding, I’m sleeping well, feeling better and definitely getting plenty of sun. I’m in the process of renewing my CrossFit coaching certification, but I’m really enjoying just being the sweaty, gray-haired guy trudging through his burpees. The old dude who just happens to be uniquely good at scaling for himself.

Biking: I’ve started biking around the island. On my first journey, I biked across the narrowest portion of Maui between Paia, on the North Shore, and Kihei, on the South Shore. The route I took was 17 miles from shoreline to shoreline. I’ve also experienced two flat tires and a pedal that just fell off. The volcanic rock has been a bit rough on the bike. On the flipside, I’m becoming buddies with the guys at the bike repair shop.

The Nice Weather Conundrum: When I was a kid, we were not allowed to stay inside on a nice day. My parents wouldn’t allow us to waste the limited number of good days that New England had to offer. This childhood rule has always stuck with me. I feel a gnawing guilt rise up inside me whenever I see the sun and blue skies outside my windows. Of course, it appears that most every day in Maui will have reason to draw me outside. At first, I thought, “No big deal. I’ll just do ‘inside stuff’ in the evening.” Well, that seemed like a good idea, but, in the evening, I’m usually exhausted from spending all day outside enjoying the fine weather. I know, not a bad problem.

Time of the Year to Move: I would recommend moving to Maui in February. I believe that the Northeast’s snow and ice would provide extra motivation. Moving in July during New England’s peak vacation and barbeque season didn’t provide much impetus. That said, Abbey is very happy that Maui has no thunderstorms.

Adventures with Natalia: Caylee’s good friend, Nat, visited during Caylee’s birthday weekend. We had a number of adventures during the time including surfing lessons, outdoor dining beside the mountains in Wailuku, watching sunset from 10,000+ feet in Haleakala National Park and dining upcountry in Kula at Ocean Vodka. It was wonderful to see Nat. We’re looking forward to seeing more friends and family in the near future.

Parosmia: In the Spring, I thought that I smelled a dead mouse at our house. I looked around the garage, basement and house, but found nothing. Cherry didn’t smell anything. It’s now a few months later and I still smell ‘dead mice’ every day. Evidently, this is a post-COVID effect. I’m looking forward to the coming months when I can smell the ocean and the flowers that grow year-round on Maui. I’m sure this will be better than imaginary deceased rodents.

Be well, take care and we’ll hope to see you sometime soon.

P.S. — I bite my tongue. It’s a bad habit.



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.