Maui — Three Month Update

Trey Whitaker
6 min readOct 16, 2022


We live on the South Shore in Kihei

Today, for the first time since moving, I thought of what I’d miss about living on Maui. That’s likely a sign that I’ve started to find a rhythm to this new life. I’ve had the opportunity to live in many different locations throughout my life and change is always a bit unsettling. That said, you find a way to carve out your own little corner. Whether it’s a bunk in an Army barracks, a studio apartment in Los Angeles or a condo in a 55+ HOA, eventually, you will make yourself at home in your new location. That’s started to happen here in Maui.

Hula dancers at the Plantation Days Festival

Plantation Days Festival: Each Wednesday, I volunteer at the Sugar Museum in Pu’unene. It’s about a 7 1/2 mile bike ride from our home in Kihei. Over the past couple months, I’ve been helping to prepare the museum grounds for a gala held on October 1st. The Plantation Days Festival celebrates the history of plantation life and the various cultures that were part of that era. At the event, we enjoyed some tasty Filipino food and all types of traditional dance including hula. It was another opportunity for us to learn about the history of the island and the diverse group of people who helped create the sugar industry on Maui.

Abbey visits Aloha Kihei CrossFit

CrossFit Abbey: Aloha CrossFit bills themselves as ‘dog-friendly’. Given this, Abbey took the opportunity to make her first gym visit since leaving Connecticut in June. Not surprisingly, she fit right in and accepted all the welcoming pets. That said, Abbey seemed a little disappointed in the lack of treats that she’d become accustomed to receiving from her friends at Tolland CrossFit.

Hiking the Keonehe’ehe’e Trail

Haleakala/Trail Steward: I’ve started a new role as a trail steward at Haleakala (House of the Sun) National Park. Once a week, I make the 90-minute drive up the side of the crater to the visitor’s center. The trip up Crater Road is only about 40 miles, but requires you to navigate one switchback and blind turn after another. The climb takes you from sea level to the summit at over 10,000 feet. Along the drive, your ears will pop and you might feel a little nauseous from the hairpin turns. My task as a trail steward is to assist hikers and help preserve the park. This past Monday, I hiked the Halemau’u Trail to a campground inside the crater. It was downhill and sunny on the way into the crater and uphill, rainy and slippery on the way out. The round trip hike of 12 miles took nearly 6 hours to complete.

Trash gathered along the Piilani Highway in Kihei

Malama: Malama means ‘to take care of’. To support this idea, I’ve spent a few Sundays picking up along a nearby highway. I listen to the NFL games while using a picker to snag items tossed on the roadside. For some reason, folks toss away a lot of plastic teeth flossers. I’ve wanted to do something to give back to the island and this is the simplest of gestures. I was inspired by the author/humorist David Sedaris. He takes daily walks near his home in England and began picking up trash along the way. Eventually, he’d cleaned up so much rubbish that his town named a garbage truck after him and he was even invited to have tea with Queen Elizabeth.

Feral chicken on Maui

Chickens and Roosters: It takes a while to get accustomed to all the wild chickens one sees while walking around. There are two stories as to why there are so many feral chickens wandering about. One tale is that a hurricane blew down all the chicken coops and they’ve been running amuck since then. The other theory suggests that its due to decades of illegal cockfighting. Either way, they do help by eating spiders, flies, centipedes and the like. I believe the main reason they’re tolerated is that they’re quick to move along. When you walk down the sidewalk, the chickens quickly scoot out of the way. They’ve learned to coexist by not being a threat and helping out with the bugs.

Maui Gold Plantation in Hali’maile

Plantation Visit: We recently made a visit to a pineapple plantation and learned a bunch of interesting tidbits from the guide. For example, 98% of the pineapples grown in Hawaii are consumed here. They are purchased by the local hotels and restaurants or sold at local markets. Since they’re consumed fresh and not canned, Hawaiian pineapples (e.g., Maui Gold, Sugarloaf) are sweeter and less acidic than most variations found on the mainland. Pineapples are actually berries and are pollinated by bats instead of bees. Also, just in case you’re looking for a career change, there’s a shortage of pineapple pickers. They’re oldest pineapple picker is 73-years old.

Viral pineapple post on Reddit

Viral Pineapples: I took lots of photos during the pineapple plantation visit and posted my favorite on Reddit. It was a big hit on the social media site. The submission earned over 52,000 upvotes and had more than 800 comments. Comment sections are always dicey, but I took a look at them to get a general sense of the themes on my post:

  • Many people were surprised at how pineapples grow. Most thought they grew in trees like coconuts.
  • Lots of folks made SpongeBob SquarePants references since SpongeBob lived in a pineapple house.
  • Quite a number of comments referred to a music video entitled ‘Pen Pineapple Apple Pen’. I’d never heard of this, but the video has a few hundred millions views on YouTube.
  • Scarily, there were plenty of people that wondered how it might feel to run through or fall into the field full of jagged edges.
  • Lastly, a few folks raised issues related to monoculture farming and the exploitation of Hawaii by companies like Dole.

Living In/Living On: I’ve lived IN quite a few cities and states, but Maui is the first place that I’ve lived ON. Most recently, I lived in Tolland. Now I live on Maui.

Newlyweds on Maalaea Bay

Beachside Weddings: One unexpected thing about island life has been the number of weddings I’ve wandered into with Abbey as my ‘plus one’. One minute, we’re strolling down along listening to our beach walk playlist and the next we’re in the midst of a wedding ceremony. This weekend, we’ve already come across two weddings. They’re usually small affairs with anywhere from one to ten attendees. In some cases, it has been just the couple plus an officiant doubling as a photographer. If you’re considering a beachside wedding in Maui, I have a couple considerations for you. Make sure to check the tides. High tide is a bad time for a wedding. The other is the wind. Winds tend to pick-up in the late afternoon. Of course, couples like the idea of wedding held as the sun is setting. I’ve seen weddings held on a sliver of beach with wind gusts spraying the attendees with sand and salt water. Not ideal.

Coming up next month: Rainbows, Wahine volleyball, what I miss/don’t miss about Connecticut, the Manchester Road Race and more.

P.S. — Beach walk playlist



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.