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There’s nothing like venturing off on a fun girls trip with your best friend. Whether you’re pampering yourself at a beautiful spa or enjoying a tropical getaway filled with exciting activities, in the words of the great Cyndi Lauper, “Girls just wanna have fun,” and we do it very well.

If there is a symbol to represent the divinity of girl getaways, Oprah Winfrey and Gayle King would certainly embody the coveted beacon. The media moguls and besties have set off on vacation to a number of destinations together over the last 30 years and according to Winfrey, her long-time relationship with her partner Stedman Graham would not have lasted if King wasn’t included in some of their adventures. The 67-year-old TV host revealed the interesting tidbit in a new series on Oprah Daily called The OG Chronicles: Joy Ride.

“If Stedman didn’t like you, Stedman wouldn’t have lasted,” she told Gayle on the show which made its debut on September 9, Ace Show Biz reported. “Husbands and boyfriends come and go. Best friends last forever,” she added.

The longtime pals reflected on their amazing 45-year-friendship while embarking on a road trip which comes 15 years after they first set out on a cross-country escapade from Santa Barbara, California, to New York City in 2006.


Gayle, 66, openly admitted that she was a “proud third wheeler” to Oprah and Stedman’s vacations over the years, and she had no shame in her game about it.

“I make no apologies for that,” the CBS news correspondent explained. “I got divorced back in 1994 and I’ve been their third wheel ever since.

“The good news is that Stedman is always very welcoming, so it never occurs to me when she says, ‘We’re going to so and so,’ I’m like, ‘When?’ It doesn’t occur to me that I’m not invited,” she continued.

“But throughout the years, we’ve gone on some great trips together. And that’s not gonna change.”

This time around, Gayle took the wheel as they head out onto the open road to visit Arlene Ramirez, “a charter member of the Oprah Daily Insiders community who lives nearby in Santa Barbara,” the Daily Mail reported.

We learn so much about our friends and even a little about ourselves when we decide to set forth into new territory with our best buds. Maybe you notice that your bestie has a fear of heights or you have that one friend who likes to stay behind and lounge in the hotel all day. While answering fans’ questions throughout their journey, Winfrey explained how she became annoyed with Gayle for singing a little too much during the last leg of their trip in 2006. The OWN founder said she became so irritated that she even asked for a football helmet to block out the noise.

“I’m not kidding. I would like a football helmet. I’ve got earplugs. I’ve got earphones. I’m going to put on plugs and a helmet. That’s the only thing that can help me,” Oprah recalled of Gayle’s annoying singing. Despite the irritating ordeal, Gayle’s bad singing wasn’t enough to break the besties’ impenetrable bond. Vacations can truly test the limits of any friendship.

Wondering where else the ladies have whisked away to?  Maybe you recall their fun “glamping” trip to Yosemite National Park in 2010. The pair set off on the fun crusade after receiving a letter from national park ranger Shelton Johnson, who wrote that he wanted to encourage more African American people to visit the national treasure. The ladies set up their camper and had a fun day exploring the park and later barbequing underneath the stars in Yosemite.



In the spring of 2015, Oprah and Gayle headed to Ibiza, a Spanish island known for its nightlife. The duo went clubbing and even bumped into during their visit. Gayle documented their exciting adventure on Instagram writing:

“They say it’s better in Ibiza!…Good times good friends!”


Oprah told fans in 2014, that after The Oprah Show ended in 2011, one of her bucket list items was to go truffle hunting, but the trip didn’t happen as quickly as she wanted it to. The Oscar-award-winner pushed the long-awaited getaway back for years until 2014. That’s when she finally decided to journey to Umbria, Italy, with Gayle and her daughter Kirby.  The two besties were invited by the Balestra family of truffle company Sabatino Tartufi which imports more than 42,000 pounds of truffles every year.

Oprah recalled their first day at the family’s lush truffle compound.

“The first day, we went with seasoned hunters and their dogs, looking for black truffles,” she wrote on her website at the time. “The black ones aren’t as delicate as the whites, and the dogs actually sniff them out, dig them up from the ground, then hold them in their mouths until the hunters come and reward the dogs with a treat. It’s kind of like hunting for Easter eggs if the eggs were buried.”

Oprah continued:

“Then all the truffles were taken back and thoroughly washed, and a truffle extravaganza ensued: three kinds of homemade pasta, pizzas with truffles, prosciutto, cheeses, chicken roasted on a spit, freshly baked focaccia with truffle honey.”

By the end of the trip, Oprah and Gayle had 15 pounds of truffles to take home to family and friends.

Imagine jet-setting off to Fiji with big stars like Ava DuVernay. That was a reality for Oprah and Gayle in 2015. The duo enjoyed a jam-packed vacation filled with water sports and relaxation for Gayle’s 61st birthday, The Jasmine Brand reported.

Two years later the inseparable buds took off to Maui to celebrate Gayle’s 63rd birthday. According to W Magazine, Oprah treated Gayle to an “almost Weight Watcher’s approved” birthday dinner bash, because you know besties need to look out and support each other with their personal goals too right?

The girls chowed down on some healthy but delectable treats including butter lettuce and pear salad, glazed carrots, skillet potatoes, and truffle au gratin cauliflower. Towards the end of the festivities, Oprah treated Gayle to a yellow cake topped off with a beautiful bouquet of yellow flowers. Gayle absolutely adores the color yellow, according to her best friend Orpah. These gal pals know each other like the back of their hands.


Gayle and Oprah’s incredible friendship speaks volumes, not just because they get to experience the world together but their 45-year-long friendship has allowed us to see them mature alongside one another throughout their careers and the ups and downs of their personal lives. They have been together with each other through thick and thin. Every woman deserves to have a friend like Gayle or Oprah by their side.

What are some memorable trips that you have taken in the past with your best friend? Tell us down below.

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