Derek Briggs first started his career on the water as a commercial diver in the Gulf of Mexico. A tough and lucrative field where he was able to test his limits, as well as finance a bit of travel.

Briggs traveled through Central and South America where he encountered great surf, hidden jungles, and the beautiful view of Machu Pichu. Along the way, he discovered something that would become a lifelong passion, sailing. He had never sailed before but after a ride from Panama to Columbia, through the San Blas Islands, he knew right away that this was an experience he wanted to replicate. 

When he returned home, he took the remainder of his funds and bought his first boat, Betty Jane, a 25 ft Oday. He taught himself to sail and ventured down to the Florida Keys where he met the love of his life, Kassy. Broke, but tan and determined to win her, he took her on a sailing trip to the reef, where they drove all day and ate lobster dinners while watching the sunset. After many sunsets and lobsters, they found their greatest treasure yet, their son Odie. 

The two traded boats in for diapers and headed to Charleston, SC to be closer to the family. With a baby on the way, it was time for Briggs to get to work. Thanks to a little fate and luck, Carefree of Charleston was starting its own little family.

Derek has been a part of the Charleston Carefree family now for over three years. Getting to know each member over the years, watching them grow both as boaters and in life has been truly special to him. The daily dock chat of new careers, babies, grandbabies, sharing in the dreams and aspirations of his members as well as his own, and the positive atmosphere is what he credits for making the dreams of his family come true. 

Derek, Kassy, and Odie now live on a 41′ sailboat, on which they hope to give their son a firsthand look at this beautiful world. In Derek’s own words, “It has been the daily discussion and motivation from our members that has gotten us here today. These last three years, making sure this Carefree family has a fun day on the water, has been truly rewarding work of which I’m very grateful to be a part of.”

To learn more about the Dockmaster program and how they are selected, click here.