Maui News

Five Dads Honored with Grand Wailea Trip from Hilton and OWN: Oprah Winfrey Network

Listen to this Article
2 minutes
Loading Audio... Article will play after ad...
Playing in :00

Just in time for Father’s Day, five deserving dads and their families will be enjoying an all-expense-paid trip to the Grand Wailea, A Waldorf Astoria Resort, provided by Hilton and OWN: Oprah Winfrey Network. 

Oprah Winfrey and co-host and actor Sterling K. Brown surprised the families with the trip during a Father Day’s Special on OWN Network. The special “Honoring Our Kings” will re-air this Saturday on OWN at 9 p.m. ET/PT and is available on discovery+.

PC: image from video authorized by / credit: “OWN: Oprah Winfrey Network”

The families will also be invited to enjoy dinner – courtesy of Grand Wailea – that will showcase the locally sourced ingredients found on the menu at Bistro Molokini, a family-friendly restaurant venue situated at the heart of the resort. 

PC: image from video authorized by / credit: “OWN: Oprah Winfrey Network”

J.P. Oliver, Managing Director, Grand Wailea, A Waldorf Astoria Resort said, “Our Grand Wailea ʻohana is looking forward to welcoming these deserving fathers to Maui and sharing our aloha with all of the dads who will be staying with us to celebrate.”

The 776 room newly refreshed Grand Wailea is situated on 40 acres fronting Wailea Beach. The resort also offers an enclave of 51 luxury villas, Ho‘olei at Grand Wailea, located nearby with access to Grand Wailea amenities.

Oprah Winfrey speaks at “Live Your Best Life” on Maui. PC: Wendy Osher / Maui Now (2017)

Oprah’s Maui Connections

Oprah has a $2.8 million property in Upcountry, Maui as well as a private road that extends from Keōkea to Kīhei. She was also involved in a 2002 purchase of oceanfront acreage in the East Maui town of Hāna.


In July of 2019, Oprah stopped by the Maui Humane Society following a wildfire to check on the animals. She snapped a photo and shared it to her Instagram. According to the shelter, Winfrey thanked staff and volunteers for their hard work and made a donation during the visit.

In 2017, Oprah hosted a public event at the Maui Arts & Cultural Center sponsored by the Hawai‘i Medical Service Association entitled “Live Your Best Life,” promoting healthy lifestyle conversations with Maui and Hawai‘i residents.


Sponsored Content

Subscribe to our Newsletter

Stay in-the-know with daily or weekly
headlines delivered straight to your inbox.


This comments section is a public community forum for the purpose of free expression. Although Maui Now encourages respectful communication only, some content may be considered offensive. Please view at your own discretion. View Comments