In the first article of this series, we asked experts what it's really like to quit your job and move to a vacation destination. The rest of the series will focus on the experiences of people who've actually done it. This installment tells the story of Glen Simkins, owner of Maui ice cream stand Coconut Glen's.

Never in his wildest imagination did Glen Simkins think he would end up in the Maui rainforest selling ice cream to tourists. A decade ago, he was a hot-shot chef who had worked at Michelin-star restaurants.

But then he decided not to do it anymore. "I was at the subway going through the motionsbut I wanted to be next to palm trees," Simkins says. "The chef industry was very aggressiveand dog-eat-dog and egotistical."

So at age 27 he sold everything he had, booked a one-way ticket to Maui, bought a Volkswagon, and started selling coconuts. He knew almost nothing about coconuts, but while living out of his Volkswagon and cooking fresh fish out of the rim of a tire, he had the idea to open up a coconut and pour rum in it; thus, Glen became an instant coconut convert. Fast forward a decade later, and he's the owner of an unassuming but colorfully decorated ice cream stand called Coconut Glen's, located along the winding, narrow Hana Highway.

Hotels in this story

Price Dates

Travaasa Hana, Maui

Hana Kai Maui

Huelo Point Lookout

Maui Ocean Breezes

Experiencing a trip along the Hana Highway is a bit like experiencing Simkins’ philosophy on life — the Hana Highway truly is about the journey, not the destination. It’s full of twists and turns (there are literally hundreds of curves, and over 50 one-way bridges), and the dozens of stops along the way include hikes, waterfalls, jaw-dropping coastal viewpoints, and black-sand beaches.

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“I hate it when people ask me if it’s worth it,” Simkins says of the tourists who inquire about the various Hana Highway attractions. Such a question is, in Simkins’ view, entirely missing the point. “Sometimes you miss the most incredible things because you’re thinking about the next thing,” he explains.

If you’re wondering about the stop at about Mile Marker 27.5, however, where you’ll find Coconut Glen’s, we’ll answer the question anyway: It’s worth it. The ice cream, which comes in flavors such as honey macadamia nut and chocolate chili, is creamy, decadent, and — shockingly — vegan. The secret of course? The coconut. And for those who like their coconut straight, Simkins still sells fresh coconuts, too, which is how the enterprise got its start.

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Simkins says it was his time staging (in chef parlance, that’s interning for free) in Europe that made him decide to change his life. He found himself working six days a week at a renowned fine-dining restaurant in the French Alps, and recalls having to hide in a World War II bomb shelter while a labor board came to inspect the premises. “It was like slave labor,” he says.

So he cut his gig there short and headed to Italy, where he ended up volunteering on an organic farm in Parma. The entire town was focused on the production of parmesan cheese and Lambrusco wine, and for Simkins it “was this revelation of how simple and really rich life could be.” There were old Italian men with canes “out of the Godfather” who used stethoscopes to test for holes in the cheese, whom Simkins drank grappa with late into the night. “For the first time I saw what it was like to be genuinely happy. Like happy without the need for things. It was like taking the red pill in The Matrix,” he says.

When he got back to Boston, his view of success had irreversibly changed. No longer did he equate success with material things — for him, now, success meant happiness. “It matters if you wake up every day excited and you go to bed fulfilled,” he says. “If I can do that every day I feel like I’m being successful.”

Coconut Glen’s outpost in Paia opened on March 2nd of this year, the birthday of Dr. Seuss; photo courtesy of Glen Simkins

But that’s not to say that his decision to move to Hawaii wasn’t without its ups and downs. Just a month after his arrival to Maui — which he picked because “it was the farthest away I could get from Boston without needing a green card” — he got a call offering him what only a short time before would have been his dream job: Executive Sous Chef at Fenway Park. At the time, he turned it down without pause. “I was on an adventure, man, and I couldn’t be stopped,” he says. But he questioned it later, when the economy tanked in 2008 and he was figuring out how to make ends meet. Nobody was buying coconuts, and nobody was taking vacations to Hawaii.

But it was during this difficult time that he had the epiphany to start making ice cream.

The operation began in his garage, with him running down his driveway to deliver the scoops. This year, he bought the property along the Hana Highway where he’d been renting for nine years, and opened a second Coconut Glen’s outpost in Paia — dubbed the Bubble Bus for its psychedelic paint job of swirls and bubbles.

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Now Simkins says he feels like he is living his fantasy life. No day is the same and every day is an adventure, but his recent activities when we spoke included going for a run with his dog, Ginger, sewing robes for Burning Man (where he brought his ice cream), chipping African Tulip Trees for his organic farm (the ingredients are harvested for the ice cream), processing passion fruit in the kitchen for his lilikoi ice cream flavor, and working on his children’s book, set in a world where ice cream grows on trees. (And Simkins points out that when you make ice cream out of coconuts, in a way it actually does.) After dressing up as Willy Wonka one Halloween, he began to identify with the character, a favorite from childhood. “We don’t have a chocolate river but we are living in a place where you can go for a walk and pluck fruit from a tree and sit down and eat it,” he says.

Simkins acknowledges that not everyone who makes a major life change like he did ends up having such a positive experience. His advice for others contemplating a major move is to not get attached to a specific outcome. “You just have to enjoy the ride. It’s not about getting there because once you get there you’re going to want the next thing.”

In the end, living a fulfilling life wasn’t really about Maui. “It’s not about the ice cream, or the farm, or the fact that it’s Hawaii, it’s about surrendering and letting go,” he says. “Letting life happen to me instead of me happening to life.”

Hotels Along the Road to Hana, Maui:

Travaasa Hana, MauiHana Kai, MauiHuelo Point Lookout, MauiMaui Ocean Breezes

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