Jon Kingsley, Jr
Right after crossing the stage at his 1987 high school graduation in Houston, Jon wasted no time. He hopped into his packed truck, determined to chase adventure. Twenty-three hours later—after two warnings for speeding—he arrived in Miami, Florida, ready to follow his dreams. His journey began aboard a 50-foot Bertram Sportfish with one goal: to fish in every major billfish tournament in the Caribbean. Living aboard full-time, Jon crisscrossed the Bahamian and Caribbean islands three times, from Walker’s Cay in the north to Grenada in the south, stopping at many islands in between.
After four years of life on the water, college, a business career, and family obligations brought him back to land. But even then, Jon couldn’t stay away from the sea—most weekends and holidays found him back on the water. Eventually, he became captain of the vessel, logging over 6,000 hours on the engines and continuing to freelance on boats up to 63 feet. By 2015, however, the fast-paced tournament lifestyle started to lose its shine. That’s when Jon’s interest turned to sailing—a huge shift for someone who once called sailboats “blow boats!”
Semi-retired from business, Jon sharpened his sailing skills, became an ASA instructor, and returned to the Caribbean. A pivotal moment came when he repositioned a 47-foot Leopard catamaran from Grenada to Turks and Caicos, solidifying his passion for sailing and making it part of his DNA.
Now at a stage where he wants to give back to the lifestyle that has brought him so much joy, Jon is eager to share the knowledge and experience he’s gathered over the years. Teaching others is his way of passing the torch, hoping to inspire a similar love for adventure in those he instructs.
Jon holds a USCG 100T Master’s license, is an ASA instructor, FAA private pilot, and an advanced scuba diver (NAUI, SSI, & PADI). And when he’s not in the air or on the sea, he’s a dedicated family man. To close, one of Jon’s favorite quotes from Anthony J. D’Angelo sums up his outlook: “Wherever you go, no matter what the weather, always bring your own sunshine.”
