Let Us Be Your Guide

Captain Jay Keeney has always enjoyed being on the water. As a child, he imagined living aboard a sailboat and exploring the seas decades before he ever set foot on a sailboat. In college, he bought a kayak (prior to ever kayaking) knowing he would enjoy it as it brought together two of his passions; boating and the outdoors. Captain Jay now holds an Operator of Uninspected Passenger Vessel (OUPV 6-PACK) license with the United States Coast Guard and is a certified US Sailing and Power-boating instructor.

A Philadelphia native, Jay followed his parents’ footsteps and attended Shippensburg University in Pennsylvania. After graduating in 2001 with a Major in Finance and a Minor in Economics, Jay joined the financial industry as a Mutual Fund and Hedge Fund Accountant. In 2005, Jay earned a Master’s degree in Finance from Saint Joseph’s University and joined another firm as an Investment Consultant. In 2008, as the “Great Recession” brought the economy to a standstill, Jay was laid-off and was ready for a change. Feeling Philadelphia and finance was not his true calling, he felt it was time for a new location and career. He packed up his car with his tent, granola bars, and road bike and decided to take a solo southern road trip stopping in Washington DC, Charlotte NC, Savannah GA, Orlando, and Tampa FL. After stopping in Charleston South Carolina, Jay decided not to leave.

Completing the location change, Jay then pivoted from finance to the software industry starting as an Implementation Consultant in 2010. There he met a co-worker, Taylor Brockman, who would become a close friend and set him on a trajectory to realize his dream of sailing. Taylor was in search of a crew to race his 26ft Ericson sailboat, Country Girl, in the Charleston Ocean Racing Association (CORA) Wednesday night races. Jay volunteered and went from zero experience to racing in the same afternoon, and was absolutely hooked. Always the outdoors-man, sailing provided Jay with a deeper connection and understanding of the natural elements including the wind, tides, currents, weather, and moon phases.

Jay then joined a software startup as a Customer Success Consultant where he enjoyed three-plus years with the organization. As fate would have it, he received a phone call during his earned month sabbatical as he started mile 1 of a 250-mile bike ride with his father, telling him he was being laid off. Turning this challenge into an opportunity, Jay decided to become his own boss, obtain his Captain’s License and start Charleston Sailboat Charters with the sole mission of exposing as many people as possible to the sport of sailing.

Captain Kathleen Saunders grew up on the Chesapeake Bay in southeastern Virginia. She often tagged along on the bow as her dad sailed, practicing for regattas. Born into a long line of sailors, Kathleen’s dad and his brothers grew up ocean racing with their dad, and he with his, and so on… The Saunders name can be found on a number of historic trophies in the Annapolis Yacht Club. But as most know, if you tell a child to do one thing, they will certainly do just about anything else. Despite growing up in yacht clubs and being raised by nationally recognized sailors, she was not interested in sailing competitively. As a teenager she took a short summer stint working on the SSV Robert C Seamans, a three-masted tall ship and oceanographic research vessel. Once at college, she took a job with the College of Charleston Sailing Association as a deckhand and assisted teaching keelboat sailing classes under Greg Fisher. However, a year after she graduated with her BFA she headed to graduate school and sailing took a backseat to “adult jobs.”

Teaching others stayed at the forefront of Kathleen’s interests in life though. After earning a MFA in Studio Art at Florida State University, she accepted an offer to join the faculty at CofC where she taught darkroom photography full-time. After a year, she greatly missed the water and left her professor position, deciding to pursue a career in sailing. Since then, Kathleen has worked full-time sailing for charter services and on boat deliveries in and out of the Charleston area.

Kathleen is the first woman in her family to sail professionally and has obtained her USCG 50-ton Master Captain License. She’s thrilled to captain Mental Heeling for the 2023 season and share her love of sailing with others. In her free time, Kathleen loves tending to her tropical garden, camping, birdwatching, sewing, and traveling. Kathleen is also an internationally recognized artist. She and her dad still sail together locally racing 420s, Y-flyers, and classic moths for fun. In the future, Kathleen hopes to sail an Atlantic crossing and also plans to follow in her dad’s footsteps by sailing in the Newport-Bermuda race one day.

Christian Naples was born in 2011. Every year he visited South Carolina where his uncle lives, who was a sailor. Every year he looked forward to going on the boat. His uncle will sometimes let him drive, he enjoyed that. He once said to his Dad, “when I grow up I want to be just like Uncle Jay.” So now all he is waiting for is to get older and get his sailing license.