Watch : Tom Brady Shares Look at “Trip of a Lifetime” With His 3 KidsTom Brady and his kids touched down in The Last Frontier. “A week in Alaska with my three best friends,” he wrote in a July 28 Instagram post. Alongside his sweet recap, the seven-time Super Bowl champ shared photos of his kids enjoying the outdoors and spending quality time with each other. Beyond this Alaskan getaway, the teens have had an epic summer vacation, which kickstarted with Jack graduating high school in June. His siblings came to support him on his big day alongside his dad, who posted photos of his family celebrating the milestone.