Top 10 Celebrities on Maui

Oprah Winfrey loves the Island of Maui so much that she bought over 60 acres of land in East Maui, and then she bought the historic Thompson Ranch near Keokea. On Oprah’s Maui farm she grows more than 100 species of local and organic produce; herbs, fruits and vegetables. Rumor has it that Michelle Obama likes to chill out with Oprah on Maui!

Even Dirty Harry loves Maui no ka oi! Not only was Scott Eastwood (his super handsome son) honored at the 2015 Maui Film Festival, but so was actor/director/producer/composer Mr. Eastwood at the 3rd Annual Maui Film Festival event back in the day. The old Mayor of Carmel loves Hawaii so much that he once bought a beachfront property in Wailea for his family.

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

Maui resident, and Aerosmith’s lead man Steven Tyler can’t get enough of the Island of Maui. 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).

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…

If you’re lucky, you might get a chance to hear Willie or his son Lukas Nelson play music at Charley’s Restaurant & Saloon in Paia during your next Maui vacation! As a longtime cherished Maui resident, Willie is obviously one of Maui’s favorite celebrities…he is one cool dude, that’s for sure!

Woody, Woody, Woody. How can we count the ways? This true detective, environmental activist, Maui lover, Kingpin, and overall talented and handsome guy is also a favorite Maui celebrity… Who doesn’t absolutely love Woody Harrelson? Oi Vey…

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. Don Nelson is a longtime favorite on the North Shore, and you might be able to give him a high-five if you catch him at his coffee shop or shave ice shop in Paia Town.

Mick Fleetwood of the notorious Fleetwood Mac band loves Maui so much that he has a property near Napili Bay, and an awesome restaurant on Front Street in Lahaina. This part-time Maui resident is definitely seen around town, and sometimes heard live behind a mic.

Shep Gordon is no stranger to magical Maui! This New Yorker is one of America’s most infamous talent managers, producers and Hollywood film agents. 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!

Hailing from the Lonestar State, Mr. Kris Kristofferson is one of Maui’s most laid back celebrity residents. This East Maui resident is a ultra-influential musician, actor, singer, songwriter, and is a former U.S. soldier. Between 1985-1995, 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.”