A vacation to Panama City in 2007 charted the course of Diana and Matt Gleason. Years of future vacations to the Destin area, wedding vows on the beach at Sandestin Resort, and Covid prompted them to seize the day and make their dreams a reality. "Why wait? Let's go live where we want to be NOW." And so, they did. "One year on June 15th," Diana proudly proclaimed when asked how long they've resided in Hammock Bay.

Originally hailing from southern New Jersey, Diana and Matt knew each other in high school but didn’t really get together until after college, when they were both living at home. “We ran into each other at a friend’s Halloween party. Matt was dressed as Superman, and I was Wonder Woman,” Diana recalled. After exchanging phone numbers and a few dates, that was it. “We aren’t just married and in love - we are one another’s best half, we are a team, we are best friends. We just celebrated our 12th wedding anniversary.”

After that first trip to the Panhandle, they began to envision their retirement amid the turquoise waters and white sandy beaches. However, neither is retired yet: Matt is a national sales rep for Workwear - so he travels quite a bit. Diana is a former professional dancer but after a hip injury and twin pregnancy, she pivoted into accounting. She started a boutique bookkeeping agency servicing small businesses nationwide, DG Consulting Services. A passionate entrepreneur, Diana enjoys coaching her clients on how to pay less in taxes and increase profit. Hammock Bay business owners can learn more about Diana’s services at www.dianagleason.com.

When the pronouncement was made to take the plunge and move to the Panhandle, Hammock Bay became their new home—a decision fueled by a desire for a better quality of life for their family. The community's lively atmosphere, complete with residents walking dogs, playing pickleball, and lounging by the pools called loudly to the Gleasons and their nine-year-old twin sons, Austin and Brady.  But it was the warmth and kindness of their neighbors that truly solidified their sense of belonging.

Around the neighborhood, Matt loves to golf and has been trying out different local courses and the driving range. Diana loves to work out and enjoys her workouts with Travel Trainer Sean Miller and Yoga at Studio 30A. Brady has been trying different sports this year, including baseball, basketball and soccer for Freeport. “Austin is our artist and frequents Estelle’s Gallery for class,” Diana said. The family also loves going to the beach and swimming in their backyard pool with friends. "We love that in 25 minutes, we can be at Grayton Beach playing with our kids between the gulf and Western Lake," Diana shared. Indeed, the versatility of the area offers endless opportunities for adventure, whether it's shopping on 30A, entertaining visitors at Crab Island, or catching sunsets at the Hammock Bay dock. 

The Gleasons are seasoned adventurers. From exploring the Dominican Republic to venturing into Northwest Idaho and Kentucky, they thrive on discovering new places together. But amidst their travels, they've also established traditions closer to home. "Because we don't have any family local to us, our new family tradition has become Gleason Family Fun Day," Diana explained. Each week, a different family member selects an adventure, and the day is spent doing something fun together.

With three cats and three dogs, two active boys with a sense of adventure, and miles of beaches to explore, the Gleasons have made Hammock Bay their home in more ways than one.