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

Jon Hamm, Anna Osceola
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.

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.

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"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."

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