Dolly Parton’s Hawaii Story Was Bigger Than Life

When legend Dolly Parton died today at 80, there was no shortage of stories about her extraordinary life. But what caught us was something much closer to home: a Hawaii life we knew something about, surprisingly deep and stretching across decades.

Dolly didn’t simply vacation in Hawaii or show up here to film a television special. She built a home early on in Hawaii Kai (Oahu), brought her family here for Christmas, put her name behind an extravagant restaurant and entertainment venture, and then devoted an entire network television production to Hawaii replete with some of the islands’ best-known performers. Nearly four decades later, after the Lahaina fire, Hawaii entered Dolly’s story one last time.

Dolly was building a life in Hawaii by 1984.

One of the best glimpses we found comes not from any celebrity tabloid, but from a February 1985 newsletter published by Sea Life Park and Waimea Falls Park. It described what happened when Dolly arrived at Waimea Falls Park with a busload of her nieces and nephews whom she’d brought from the mainland for the holidays.

The newsletter called them the “Hillbillies in Hawaii” gang and explained that the Hawaii vacation was a Christmas present from “Aunt Granny,” the name Dolly’s nieces and nephews called her. Riding along were local entertainer Norm Compton and Hugo Logan, Dolly’s contractor for her new Hawaii Kai home.

Dolly wasn’t staying at a Hawaii resort between performances. Instead, by late 1984, she was building a home here while bringing a large part of her family to Oahu for Christmas.

The Oahu property later became known as the Dolly Parton Estate, a plantation-style beachfront home in the Portlock area of Hawaii Kai. Dolly reportedly purchased and extensively remodeled the property before eventually selling it.

Then Dolly Parton tried to open a restaurant in Hawaii.

Three years later, Dolly went even grander. In 1987, Dolly Parton’s Dockside Plantation opened in Hawaii Kai, an ambitious restaurant and entertainment operation built around one of the most recognizable personalities of all.

This wasn’t a restaurant that just licensed her celebrity name. Dolly’s image and personality were everywhere, right down to restrooms that were labeled “Buoys” and “Gulls.” The menu mixed Southern ideas with elaborate restaurant food that was fashionable at the time, including deep-fried sweet potato sorbet, chicken with avocado and Muenster cheese, shrimp scampi, as well as her traditional biscuits, fried chicken, and pecan pie.

Dolly attended the star-studded opening, although an interview filmed there revealed something that may have foreshadowed problems that were to come. She said that opening day was the first time she’d actually had a chance to see the finished place.

For Dolly, whose instincts proved to be spot on across music, movies, television, Dollywood, and a long list of businesses, Dolly Parton’s restaurant, Dockside, turned into one big and memorable flop. Disappointing food, expectations that Dolly herself might actually be seen there, and an odd concept that never quite worked were cited as causes of the failure. Whatever the reasons, it was short-lived.

“Dolly – My Hawaii” was far more than scenery.

Dolly was not done with Hawaii. On February 6, 1988, ABC broadcast “My Hawaii,” an episode of Dolly’s lavish prime-time variety series filmed in the islands. The show’s cast was amazing, including Palani Vaughan, Melveen Leed, the Brothers Cazimero, Danny Kaleikini, Al Harrington, Danny Couch, and other Hawaii performers who were woven throughout the show.

She sang “Paniolo Country” with Melveen Leed, “The Hawaiian Wedding Song” with Danny Kaleikini and “Blue Hawaii” with Al Harrington, then closed at Waimea Falls Park with the Honolulu Boys Choir. Some of Hawaii’s best-known entertainers were part of the production that reflected a period when Hawaii had become a big part of Dolly’s personal and professional life.

Maui brought Dolly back into Hawaii’s story.

In 2024, a year after the Lahaina fire, Dolly joined Felix Cavaliere of The Rascals for a new recording of “My Hawaii,” with all proceeds directed to the Maui United Way Maui Fire Disaster Relief Fund for people who had suffered losses in the fires.

This was a completely different “My Hawaii” from the Kui Lee song Dolly performed on television back in 1988. Cavaliere and Eddie Brigati had written their “My Hawaii” decades earlier. Dolly added vocals to the 2024 recording. When Cavaliere spoke about the difficulty of describing what Hawaii puts in your heart, Dolly responded that it was especially true once your heart had already seen the magic of the islands.

Coming from someone whose Hawaii history had already stretched back at least forty years, the words carried more weight than most listeners probably realized. Dolly’s contribution was one among many efforts to help after the fires, but it forms an unexpectedly fitting final chapter in this story.

But Dolly Parton’s Hawaii story lasted much longer than any one part of it. What started as a place where she built a home and brought her family became part of her business ambitions and her music, and decades later, Hawaii was still there when she needed it, and she was able to help. For someone whose life was famously bigger than life, her Hawaii chapter turned out to be considerably bigger than we even realized.

Did you know Dolly Parton had such a deep and lasting connection to Hawaii, or is there another part of her Hawaii story you remember?

Photo Credit: Dolly Parton at Kahala Hilton in 1884. From Wikipedia.

By Rob and Jeff, Beat of Hawaii.

Some of the most meaningful parts of Hawaii are the ones visitors walk right past without knowing they are there. We’ve spent nearly 20 years finding them firsthand for BOH as full-time Hawaii residents reporting on travel, culture, and island life, and telling you what they mean for your trip. Join us →