Top 10 Celebrities on Maui

As the top travel destination in the United States, Hawaii attracts tourists from all over the country and the world. People flock to Hawaii For its sandy beaches, clear ocean waters, breathtaking landscapes and super laid-back vibes. Everyone wants to escape to Hawaii and celebrities are no different!

While some come to the Aloha State for a quick getaway, others choose to stay longer and lay some roots because they fall in love with the islands. How could they not?!

Top Maui Celebrity Willie Nelson

Maui, like all of the Hawaiian Islands, is definitely a popular place for celebrities and the more fortunate folks to purchase land and vacation homes. Apart from living in paradise, celebrities choose Maui because its residents are known to embrace them while respecting their privacy. These are just a couple of reasons why celebrities love living on Maui, whether they are full-time or part-time residents. It’s just comfortable here!

Check out a handful of Maui’s most loved celebrity residents in the list below!

01

Oprah Winfrey

One of the most famous celebrities in Maui (and one of the richest) is talk show host, Oprah Winfrey! Aside from owning over 60 acres of land in East Maui, Oprah also bought the historic Thompson Ranch near Keokea in 2005 and turned the place into a charming modern farmhouse. The media mogul loves Maui so much that she recently purchased more land in Kula, next to her vacation home!

Located on the slopes of Haleakala, Oprah’s Maui farm grows more than 100 species of local and organic produce, herbs, fruits and vegetables, which she generously distributes to the local community.

Although she initially stayed away from the public eye while on Maui, Oprah has made a few appearances in the last few years including a visit to the Maui Humane Society and hosting an event to promote healthy lifestyle called “Live your Best Life.”

We suspect that Oprah has the occasional celebrity visitor. Rumor has it that Michelle Obama likes to chill out at the farm on Maui, maybe even getting her hands dirty!

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02

Clint Eastwood

Even Dirty Harry thinks Maui is No Ka Oi! The old mayor of Carmel loves Maui so much that he bought a beachfront property in Wailea for his family.</ br> Not only was Scott Eastwood (his super handsome son) honored at the Maui Film Festival, but so was actor/director/producer/composer Mr. Eastwood at the 3rd Annual Maui Film Festival event back in the day. He’s still known to drop by the festival as often as he can.

“I love Maui. What’s not to love?” (Clint Eastwood, 2002)

03

Steven Tyler

There’s so much to say about Steven Tyler. As a former American Idol judge and Aerosmith’s lead man, Steven can’t get enough of the island of Maui. That’s why he purchased a home in Wailea in 2012. Frequently seen out on the town, Steven also likes to make random appearances playing with famous musicians like Hawaii’s Willie K., and Mick Fleetwood (also a Mauian).

A recovering alcoholic and drug addict, Steven has spoken to the Maui Drug Court graduates several times, and tries to influence the Maui youth and the ones in need of direction.

I’ll bet you didn’t know that Steven has a Hawaii bill named after him! In 2013, the Aloha State passed a law to protect celebrities from paparazzi when on their private properties. It is known as—you guessed it—the Steven Tyler Act.

Steven also has a new neighbor, billionaire tech mogul Jeff Bezos, who bought a massive ocean front property in 2021, steps away from La Perouse Bay. I wonder if they’re kicking it together…

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04

Owen Wilson

Owen Wilson can be spotted sweeping the ocean on his SUP on Maui’s North Shore, or jaunting the aisles at local organic grocery stores. One thing about seeing this “Wedding Crasher” on Maui, he definitely rolls with the cool crowd and blends in with the local culture quite nicely! He’s also known for making regular appearances at the Maui Film Festival.

“I always get excited when I get to the ocean. Surfing, diving, swimming… It doesn’t matter, I just love being in the water,” Owen has said. No wonder he likes the Maui life!

05

Mick Fleetwood

Renowned drummer and member of the legendary band, Fleetwood Mac, Mick Fleetwood loves Maui so much that he has a property near Napili Bay. Besides being a famous rock star, Mick is one of our favorite celebrities in Maui because he also owns an awesome restaurant in Lahaina, where he likes to occasionally drop by to greet his guests. You should definitely check out Fleetwood’s on Front Street for some great food, delicious cocktails and live music. Oh, hey! The rooftop bar is a great place to chill out and watch the North Pacific Humpback Whales breach during the winter months.

Now retired from touring, Mick is a full-time Maui resident and chances are high you’ll see him around town, and sometimes even hear him live behind a mic. Mick is enjoying jamming with his new Maui-based band, so keep an eye out for upcoming shows at his bar. Intimate ambiance guaranteed!

If you’re looking for new fun things to do in Paia, check out Mick’s House of Fleetwood, a new store and gallery right at the entrance of town on Hana Highway. There you’ll find all sorts of fun merchandise including Maui-made clothing, vintage rock band T-shirts, Fleetwood Mac accessories, jewelry and ukuleles—all of the things that make Mick and his family happy!

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06

Shep Gordon

Shep Gordon is no stranger to magical Maui! This New Yorker is one of America’s most famous talent managers, producers and Hollywood film agents, and one of our favorite celebrities on Maui. Shep has always been a welcome addition to the Maui scene with his calm demeanor and ultra cool vibes. In the past, Shep Gordon got his start with counter culture icons like Janis Joplin and Jimi Hendrix. Right on!

This full-time Maui resident is often spotted dining around Kihei and Wailea where he also owns Humble Market Kitchin with celebrity chef Roy Yamaguchi. He is very invested in the Maui community and serves on the board of the Maui Food Bank. Mahalo, Shep! We love your aloha spirit!

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07

Willie Nelson

As a longtime cherished Maui resident, Willie is obviously one of Maui’s favorite celebrities. He is one cool dude, that’s for sure! His super talented son, Lukas Nelson, also recently purchased his first home in Haiku, on the North Shore of Maui. Sadly, Charley’s Restaurant & Saloon in Paia, where Willie was known to drop in for an improvised show, closed its doors for good in 2021 after half a century. We hope that won’t stop the country musician from playing surprise performances around Maui again.

“Maui has this spiritual quality. It’s in the air, the mountains covered in mist, the exotic plants, the wildlife, the sea, the sky, the wise kupuna who tell stories that connect the mysteries of nature to the mysteries of men”
– Willie Nelson

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08

Woody Harrelson

Who doesn’t absolutely love Woody Harrelson? The handsome Natural Born Killers and Zombieland actor is also an environmental activist, yogi and sexy vegetarian (that’s what PETA said!) and one of our beloved celebrities on Maui.

Woody picked a more isolated area of the island to set up roots. He actually owns two homes on Maui: one near Hamoa Beach in Hana, in East Maui, and the other in the remote town of Huelo, where he lives with his wife and three daughters.

An open cannabis enthusiast and supporter of its legalization, Woody also tried to open a hemp dispensary in the Aloha State in 2016 but was not selected by the health department.

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09

Don Nelson

Anyone up for a poker game? Well, good luck getting into Don Nelson’s exclusive crew of Maui card slingers! This former NBA player and head coach is probably the tallest man in Paia Town,, not to mention one of the friendliest celebrities on Maui. Nellie, as most people call him, is a longtime favorite on the North Shore, and you might be able to give him a high-five if you catch him walking around Paia.

Oddly enough, Nellie is not a fan of water activities and prefers to stare at the ocean rather than get too close. You won’t find him speeding across the water in Ho’okipa, unlike his neighbor and friend, Owen Wilson.

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10

Kris Kristofferson

Musician, actor, singer, songwriter, and former U.S. soldier, Kris Kristofferson is one of the most laid back celebrities in Maui. Between 1985 and 1995, he was part of a country music group called The Highwaymen with Johnny Cash, Waylon Jennings, and Maui resident Willie Nelson. He’s also well remembered for writing and recording musical hits like “Me and Bobby McGee,” and “Sunday Mornin’ Comin’ Down.”

After 50 years of touring, Kris has retired to his longtime home in Hana, in East Maui, where he raised his five children with wife Lisa Meyers. The couple is very invested in the community and made generous donations to the secluded town’s school system. Kris also enjoys improvised shows with local musicians, so if you think you recognize him playing under a hut in the jungle, it might just be him!

“I want to stay right where I am, which is on an island with no neighbors and 180 degrees of empty horizon. It’s a beautiful view,” Kris told Closer Weekly in 2021.

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Mahalo for reading Pride of Maui’s 10 Celebrities on Maui blog post! Which celebrities have you seen on Maui? I saw Mr. Big (Chris Noth) on Baldwin Beach once—that was fun!

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