Tom Brady is soaking up family time overseas. The retired NFL legend recently jetted to Milan, Italy, with two of his children to take in the excitement surrounding the 2026 Winter Olympics, and by the looks of it, the trip was one for the memory books.
Tom Brady has ‘the best trip to Milan’ with kids for 2026 Winter Olympics
The 48-year-old former quarterback shared a carousel of photos on Instagram featuring son Benjamin, 16, and daughter Vivian, 13, whom he shares with ex-wife Gisele Bündchen. Brady captioned the post with heartfelt reflections on exploring a new city together.
“We had the BEST trip to Milan ?? to cheer on some incredible sports stars while spending quality time exploring and learning from so many new people and places!” he wrote. “Relationships are built on shared experience and there is nothing like finding new cities to spend time with the people you love (just missing you Jack during basketball season back at home ❤️).”
In addition to Benjamin and Vivian, Brady also shares son Jack, 18, with ex-girlfriend Bridget Moynahan. During the trip, Brady thanked Delta, Zlatan Ibrahimović, and AC Milan for their hospitality, joking that he “won the gold medal for pizza” while abroad.
Beyond the vacation snapshots, Brady has continued to open up about fatherhood. In a recent conversation with Benjamin on Instagram’s “Carversations,” he explained why he sends his son motivational content rather than just funny memes. “If I’m going to share stuff with you, I want you to see real value in it,” he said.
Brady has also reflected in his newsletter about what makes a “great father,” emphasizing that being an example through dedication and work ethic matters just as much as bedtime stories. “Your children are watching everything,” he wrote, adding that showing up consistently is what truly counts.
Originally written by Samridhi Goel on Momtastic.
