By Kara Pound
A native St. Augustinian and President and CEO of The Bailey Group, Mark Bailey, Sr. learned to surf at the wee age of 5 with his older brothers, John and Bruce, at the St. Augustine Beach Pier. “They both had very different styles, and were really good,” Bailey recalls. “What still surprises me to this day is that they quit surfing at some point. I’ll have to be physically unable to surf before I hang it up.”
For Bailey, who is an integral member of the family’s insurance/ financial services firm The Bailey Group, surfing is something he’s always tried to fit in around his work schedule, and vice-versa.“I make sure to look ahead and understand what the forecast looks like before setting any appointments or making commitments on the days the waves are supposed to be good,” Bailey admits. “The waves are good in St. Augustine so infrequently that I have to take the opportunity to get a session in when I can.”
These days, Bailey says he gets out two to three times a week. But when it comes to traveling out of town, surfing is always at the top of his mind. “My very first surf trip was to the Abacos in the Bahamas in the early 1980s,” he explains. “That was also my first experience surfing over a reef, which I fell in love with. I followed that up with a trip to Costa Rica, and have been back there numerous times. Since then, I’ve been on close to 50 surf trips to destinations all over the world, including Fiji, Indonesia, Nicaragua, Dominican Republic, California and Mexico, just to name a few.”
As for his favorite spots to surf around the First Coast, Bailey says you can typically find him on the north or south side of the pier.
“Growing up, I spent a ton of time out at Vilano Beach and Anastasia State Park, surfing Blow Hole and Middles,” he reveals. “During the work day, I’d throw my baggies on and go surfing. Then I’d come back, throw my suit back on — all sticky and salty — and head back into the office. I introduced surfing to all of my kids. I would say the two that really enjoyed it the most were Cassidy and Brooks. Surfing is life for Brooks.”
With a busy work schedule running The Bailey Group, and spending time with his friends and family, Bailey says that the benefits of surfing are plentiful and keep him engaged in the sport.
“As I age, surfing provides a motivation for me to stay in shape because there are some days that I feel like I can surf as well as I did when I was younger,” he says. “Some of my closest friends in life I met through surfing, and the culture that goes along with it.”











