Rhett Bailey

A Florida native, Rhett has called Stuart, Florida home for the past 47 years and has spent

virtually his entire life around boats. His relationship with the water began at age six, when his father built him a wooden rowboat. By age 11, he had already built his first boat himself,

following a set of mail-order plans. Growing up, family vacations meant fishing and lobstering in the Florida Keys, and it was not long before boats and fishing became much more than a hobby — they became a way of life.

His first job was at a local boatyard, where he painted bottoms and performed general yard work. That early experience developed into an extensive knowledge of high-end vessel maintenance, including varnish work, mechanical and systems maintenance, and managing boatyard periods from start to finish. He began working aboard charter fishing boats out of Stuart as soon as he was old enough to drive, eventually working his way through college by charter fishing and tournament fishing.

After graduating from Florida State University with a Bachelor’s degree in Political Science,

Rhett spent several years working for the Florida Secretary of State’s Division of Elections and as a legislative aide for a member of the Florida House of Representatives. While his career had temporarily taken him away from the water, sportfishing never left him. In 1993, a trip to Bimini to giant bluefin tuna fish aboard the legendary 40-foot G&S Raptor with Captain Peter B. Wright proved to be a turning point. That experience hooked him on sportfishing as a career and ultimately brought him back to the boats.

From there, Rhett built a career that has taken him around the world and aboard some of the most respected sportfishing boats ever built. He worked alongside Captain Peter Wright aboard the legendary 40-foot Woodnutt Duyfken in Australia and was part of the crew that completed the build of the 75-foot Merritt Can’t Touch Dis in 1996. His experience includes working aboard Merritt, Paul Mann, Mark Willis, Viking, Hatteras, Bertram, G&S, Whiticar, American Custom, Jim Smith, Woodnutt, and O’Brien boats.

His fishing experience spans an impressive range of destinations and fisheries, including the Bahamas, Mexico, the Dominican Republic, Bermuda, the U.S. East Coast from Cape Cod to Key West, Venezuela, Australia, the Virgin Islands, Panama, Costa Rica, Nova Scotia, and the Florida Keys. He spent 10 seasons fishing in Australia, including nine aboard the legendary 31-foot Bertram Chamois Free. His tournament fishing career dates back to 1991 and includes years of experience chasing billfish at some of the world’s most competitive tournaments.

For 10 years, Rhett was employed by Viking Yacht Company as a member of its Demo Crew as a mate and a captain, fishing tournaments, participating in major boat shows, and conducting customer sea trials. His tournament accomplishments include three Stuart Sailfish Club Light Tackle Tournament wins, Top Boat at the 2009 White Marlin Open, second-place heaviest white marlin at the 2007 White Marlin Open with a 78-pound fish, heaviest tuna at the 2017 White Marlin Open, first place for heaviest white marlin at the 2019 Mid-Atlantic Tournament, and first place at the 1993 Dunk Island Invitational in Australia. He was also the wireman aboard the boatwhen 11-year-old Alex Johnston caught his 863-pound black marlin, which earned the IGFA Junior World Record.

For the past 13 years, Rhett has served as captain of the 62-foot Viking InTents, fishing

extensively throughout South Florida, Charleston, South Carolina, Ocean City, Maryland,

Hyannis, Massachusetts, the Bahamas, the Dominican Republic, and Isla Mujeres, Mexico. 2026 marks his 22nd year fishing out of Ocean City, Maryland.

With a lifetime spent not only fishing on boats but working on them, maintaining them, running them, building them, and competing aboard them, becoming a yacht broker in 2018 was a natural progression. Initially entering yacht brokerage as a way to supplement his income, Rhett quickly discovered that his decades of hands-on experience gave him something uniquely valuable to offer his clients: the ability to understand a boat beyond its lines and amenities and to help buyers recognize the differences between a boat that simply looks right and one that is truly right for them.

Today, Rhett specializes in helping clients navigate the purchase and sale of sportfishing boats and yachts with the same straightforward approach he has brought to the water throughout his career. He understands what it takes to maintain a high-end vessel, how boats perform offshore, what makes a great fishing platform, and where the real value lies in a boat.

Honest, competitive, and no-nonsense, Rhett believes clients deserve straightforward advice and a broker who will put experience ahead of salesmanship. Being on the water chasing billfish is where he is happiest, and his goal is simple: to help his clients find their own happy place while finding the right boat and the right value along the way.