In Photos: Jackson Holliday and wife Chloe take romance underwater with snorkeling adventure followed by cozy dinner date in Hawaii

Jackson Holliday is gearing up for his second season in Major League Baseball, and he is hoping that it goes better than his rookie season did. The Baltimore Orioles infielder had to bounce back and forth between Triple-A and the American League East Division in 2024. He has been spending time this offseason training back in Oklahoma.

The MLB offseason is long, and that does give every player some time off to relax and enjoy some vacations. Jackson Holliday is spending his December with his wife, Chloe, and they are enjoying some time in the sun.

Chloe Holliday posted a number of photos of herself with Jackson as the two are wrapping up the month of December.

Holliday Vacation

The Instagram story from Chloe Holliday shows the young couple doing a number of different water activities, including some scuba diving. The love between Jackson Holliday and his wife is also evident as Chloe shares a selfie of herself being kissed by the young star.

Jackson and Chloe recently celebrated their second wedding anniversary, and she has been with him since they were both in high school. As Jackson Holliday continues to grow and develop into an MLB star, Chloe Holliday will see her stock rise as a famous MLB wife.

Jackson Holliday could soon see brother in MLB

Jackson Holliday was getting plenty of attention as a high school baseball player in Stillwater, Oklahoma, and not just because his dad was an MLB superstar.

Matt Holliday, Jackson's father, played Major League Baseball for 15 years and was a seven-time All-Star during his successful career. Matt Holliday has spent his retirement training son Jackson, and his other son, Ethan.

Ethan Holliday is still playing baseball at Stillwater High School in Oklahoma, but he is already getting lofty expectations thrown his way. In early December, MLB Pipeline ranked Ethan Holliday as the top overall draft prospect for the 2025 MLB Draft.

Jackson Holliday will be able to share his own experiences of being the top overall pick if that were to happen to his brother.

Jackson Holliday will soon have to report back to the Baltimore Orioles, but he has been making the most of his time off with wife Chloe.