Entertainment TV Jon Hamm and Anna Osceola Enjoy Fun Day of Swimming and Snorkeling While Vacationing in Italy Anna Osceola appeared alongside Jon Hamm on the final episode of Mad Men in 2015 By Dory Jackson Dory Jackson Instagram Twitter Website Dory Jackson is an Associate Editor for PEOPLE's digital TV team. While at the brand, she's had the opportunity to interview a long list of celebrities, from Kate Hudson to Pierce Brosnan to Billy Porter. She also recaps popular TV shows like The Real Housewives of Beverly Hills and Vanderpump Rules.The New York-based Maryland native graduated from Randolph-Macon College in May 2016 with a focus in Communication Studies and Journalism. She came to PEOPLE in March 2021 after working at a number of major news companies, including Newsweek and Us Weekly. She also previously co-hosted a podcast called "Idol Nation." People Editorial Guidelines Published on September 7, 2021 05:45 PM Share Tweet Pin Email Photo: MEGA Jon Hamm and Anna Osceola are enjoying some fun in the sun during their Italian getaway. Hamm, 50, and Osceola, 33, were spotted on a boat on Tuesday near Arco dell'Elefante in Pantelleria, where the couple enjoyed time in the water. In a photo obtained by PEOPLE, the Mad Men alum appeared to hand a snorkel and goggles to Osceola, who stood on the back of the boat. Osceola appeared on the final episode of Mad Men in 2015; she played the receptionist at the spiritual retreat where Don Draper (Hamm) ended up. Word of Hamm dating his one-time costar first spread in June 2020. They were seen leaving a coffee shop together in 2017, along with a number of outings from last year, including picking up dinner and playing tennis together. Meet Splash! Jon Hamm Adopts Adorable Rescue Dog Who Was Previously Returned to Shelter Twice Prior to Hamm's relationship with Osceola, the actor sparked dating rumors with producer Lindsay Shookus. The pair were spotted attending a Broadway play together in September 2019. Hamm was previously in a long-term relationship with actress Jennifer Westfeldt. In 2015, PEOPLE broke the news of the pair's split after 18 years together. Never miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories. "We will continue to be supportive of each other in every way possible moving forward," they said in a joint statement. Nearly two years after parting ways, Hamm explained how his split from Westfeldt, 51, had been challenging. "It's hard. It's hard to be single after being together for a long time," he told InStyle at the time. "It's really hard. It sucks."