Gayle King Shocks Oprah Winfrey With Never-Been-Done-Before Gift on Vacation

The duo return for a new episode of their web series, 'The OG Chronicles,' where Gayle surprised Oprah!

Gayle King and Oprah Winfrey have been on many exciting adventures together, but their trip to a wellness retreat in Italy earlier this year was an especially memorable journey.

In a new episode of the duo's web series, The OG Chronicles -- a series in which Winfrey and King answer readers' questions, chat about trends and "delightfully riff off each other" -- the close friends break down their different approaches to traveling and reflect on their recent jaunt to Palazzo Fiuggi in central Italy.

Winfrey shares that she invited King, King's daughter, Kirby Bumpus, close friend Ava DuVernay and their friend Urania with her to Italy. "This last vacation was so meaningful to me because it was a full-circle moment to be able to take all of my friends on vacation," she says.

King reveals that the former talk show host paid for everyone to go, which she happily accepted. And while the five-some enjoyed many aspects of their trip together, there was a significant moment that stood out to Winfrey. 

"So we went on a shopping spree too, and I love a good shopping spree. Nothing better than to be able to shop and fit in the clothes, and y'all know I got new knees so I can fit in the clothes," she recalls in the episode. "I was going to my favorite store and they had pulled out racks of things and I was [choosing] things, and at the end when I went up to pay the bill, they said Gayle had already paid. That was the first time that ever happened to me!"

The two have an adorable mini celebration onscreen, clasping hands as they beam at one another. "That was a first! I was so happy to be able to do that because I've never been able to do that before," King shares.

Winfrey reveals that the occasion was "so memorable" for her because it was the first instance of her receiving when she's used to giving. "I've done a lot of shopping sprees for other people but no one's ever done that for me. But now, you know Gayle, she's on CBS and CNN," she adds, jokingly.

In March, Winfrey and King shared a hilarious look at their notedly different approaches to traveling on Instagram. The friends documented their trip together to Jordan, where they explored the desert and all it had to offer, including a chance to travel with camels. In one photo, Winfrey poses beside the working animal, giving the camera a duck face to rival that of the resting camel.

"Visited Jordan this week, and there was so much to see and experience," Winfrey captioned her Instagram post, joking that "it takes 3 days to really see it all" but she and King "only spent 3 hours." 

"We visited the site where John the Baptist baptized Jesus, Petra and all its fascinations, camels, and the spot where the big boulder comes rolling out of Indiana Jones. So much history there in the 'Rose City,' voted one of the 7 new wonders of the world," Winfrey wrote. "Put it on your must see list if you haven’t already!"

Meanwhile, King shared a different perspective of the trip, sharing a behind-the-scenes video of their journey to the Dead Sea. In the video, the CBS Mornings host prepares for a Dead Sea "float and mud bath," clad in a bathing suit and shower cap. "It feels great," King says as she's covered in mud before heading into the water. "I do wish it wasn't raining, but it feels great. We're at the Dead Sea, people. We have to do it!" 

It's clear that Winfrey also had some feelings about the rain considering that, when the camera pans to feature her, she's standing several feet away from King, sheltered under an umbrella and fully clothed. Waving from under her umbrella, Winfrey jokes that she's "doing just fine" as she watches her friends get ready to jump into the water. 

"I have a facial at 2:30," she adds to the laughter of the group, before announcing that she's going to "mosey on back, my purse is getting wet."

Fans can check out more of the pair's adventures at and watch the full video of the new The OG Chronicles episode to hear them dish about travel trip traps.