It’s smooth sailing for Kris Jenner and Oprah Winfrey. The superstars, aged 70 and 72 respectively, were spotted arriving in Mallorca, Spain for a boating vacation this week. The Kardashian-Jenner matriarch, who also counts Ellen DeGeneres as a close friend, looked summer chic in a polka dot dress, wide-brimmed black hat, sunglasses, and Mary Jane ballet flats.The mom of six carried a coordinating Hermès tote bag and wore huge diamond earrings, in keeping with her glitzy surrounds. Meanwhile, her former talk show host pal paraded around a dock in a cropped shirt and high-waisted khaki-colored trousers.A summer trip to Spain appears to be something of an annual occurrence for the pair, who sailed aboard David Geffen’s luxury superyacht there last year. Kris Jenner and Oprah Winfrey were spotted arriving in Mallorca, Spain for vacation this week The 72-year-old former talk show host wore a cropped, white, button-up shirt and high-waisted khaki-colored trousers The duo was accompanied on that trip by Winfrey’s longtime BFF, Gayle King, 71. There, Jenner gifted Winfrey and King pieces from daughter Kim Kardashian’s SKIMS x Roberto Cavalli collection. In photos shared to their Instagram accounts at the time, the trio posed while modeling the boldly printed kaftans on a boat. King wrote in a post at the time, ‘Don’t you love when you admire what someone’s wearing and THEN they give you one?’Jenner and Winfrey have known each other for years, and their friendship appeared to deepen when they each attended Jeff Bezos and Lauren Sanchez’s Italian wedding last summer.In 2012 Winfrey interviewed the Kardashian family at their home, a moment Jenner later gushed over. Posting a photo with the talk show queen, Jenner effused on Twitter (now X), ‘Best day ever @oprah!!!! We love you!!! Thanks for spending the day with us!’ Winfrey added oversize brown sunglasses and slipped her feet into a pair of white sneakers The 70-year-old Kardashian-Jenner matriarch wore a flowy black dress covered in white polka dots She added a gold belt at her hips and accessorized further with a wide-brimmed black hat Jenner passed her Hermes handbag to an assistant before getting onto the watercraft She looked glamorous in black sunglasses and Mary Jane ballet flats while receiving a hand in getting on the yacht Jenner’s signature jet black short hair was cut into a sharp bob that fell from her hat in a straight style Winfrey’s voluminous head of chocolate-brown tresses was arranged in an off-center part as the locks fell over her chest. She and Jenner have previously holidayed together, most recently in Spain last July, where they were joined by the media maven’s BFF Gayle KingOver the past year, Jenner has been soaking up the results of her dramatic face lift, executed by Dr. Steven M. Levine. The talent manager told Vogue Arabia in September 2025 that undergoing cosmetic surgery is her way of ‘aging gracefully.’ ‘I had a facelift about 15 years ago, so it was time for a refresh,’ she divulged. ‘I decided to do this facelift because I want to be the best version of myself, and that makes me happy.’ Last summer, Jenner and Winfrey sailed on David Geffen’s yacht with Gayle King. The group is pictured in a social media snap Gal pals: The high-powered trio are seen summering in Spain last year. It’s unclear whether King joined Jenner and Wingrey for the current trip ‘Just because you get older, it doesn’t mean you should give up on yourself. If you feel comfortable in your skin and you want to age gracefully – meaning you don’t want to do anything – then don’t do anything. ‘But for me, this is aging gracefully. It’s my version.’Winfrey, meanwhile, has been showing off her dramatic weight loss – which she has openly revealed was achieved with the use of a GLP-1 medication.