Jon Hamm and his wife, Anna Osceola, were photographed enjoying a day on the Amalfi Coast on Monday, marking the couple’s second wedding anniversary. The two were seen swimming and relaxing on a cove-side jetty in Minori, the coastal town on the Sorrentine Peninsula often called the "City of Taste."
Osceola, 37, wore an underwire bandeau top and Brazilian-style bikini bottoms while Hamm, 54, wore purple-patterned swim trunks. Photographs captured the pair taking a plunge from a cabana ladder into warm sea water amid roughly 80 percent humidity and temperatures near 80 degrees Fahrenheit. After the swim, Hamm wrapped a pink-striped towel over his shoulders and the couple shared a quiet toast with what appeared to be iced tea.
Hamm, best known for his Emmy-winning role on Mad Men, and Osceola met while working on the series' seventh season finale, which was filmed in 2013–2014. The pair were first publicly linked in 2017 and became red-carpet official in 2022; they married two years ago. Hamm is 17 years older than Osceola.
The couple’s time in Minori drew attention not only for the setting — an ancient resort town that includes a Roman Maritime Archaeological Villa dating to the first century — but also for small personal details that have followed the actor through recent years. Hamm, a St. Louis native, adopted a rescue dog named Splash during the COVID-19 pandemic. He completed inpatient treatment for alcoholism about a decade ago and has in recent interviews discussed hopes of starting a family. "[Marriage] has been great. And I hope it turns into kids," Hamm told The Hollywood Reporter last year. "It's not lost on me that I'm 53. I will be the old dad, but so it goes. It could be a good thing. We'll see."
Osceola has pursued acting roles in projects connected to Hamm. She has a recurring role as Maggie Haber on Hamm’s dark comedy Your Friends & Neighbors and has appeared in other productions Hamm has executive produced. Hamm is set to produce and reprise his role as financier-turned-thief Andrew "Coop" Cooper in the series' second season, which is scheduled to premiere next year on Apple TV+. Creator Jonathan Tropper has described the storyline as focused on the character's risk-and-reward calculations rather than an escalation into a crime-empire arc.
Before audiences see Hamm in that role, he returns this week to Apple TV+ in the fourth season of The Morning Show, reprising the role of tech billionaire Paul Marks. He also has a voice role as Mayor Jerry in Daniel Chong's sci-fi comedy Hoppers, which is scheduled for U.S. and U.K. theatrical release next March.
Hamm’s personal life has been a subject of media attention for years. He was previously in an 18-year relationship with producer-writer Jennifer Westfeldt; the pair separated in 2015. Hamm's mother, Deborah, died of colon cancer when he was 10, a loss he has cited in interviews. Osceola grew up in Massachusetts and has been described in media accounts as pursuing a quieter public profile while working in the entertainment industry.
The images from Minori represent a private moment for the couple amid busy professional schedules and ongoing projects. Hamm continues to balance acting roles with producing duties, while Osceola expands her on-screen credits in projects connected to those efforts.