The Captains

Captain Jay Keeney



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 Minor in Economics, Jay joined the financial industry as a Mutual Fund and Hedge Fund Accountant. In 2005, Jay earned a Masters 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 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 Kyle Parrott


Even though Kyle grew up in the mid-west, he knew he had to live closer to the coast.  In 2011, he made the move to coastal South Carolina and immediately fell in love.  Since that time, Kyle has obtained not only his 50 Gross Ton Masters License  but is also an American Sailing Association Instructor certified to teach ASA 101, ASA 103, ASA 104, and ASA 114.

Kyle joined Charleston Sailboat Charters and Searenity Charters in 2022 and looks forward to sharing his passion of being on the water and exploring the beauty that the Charleston waterways has to offer.

Captain Bob Seymour


Captain Bob has been exploring the waters in and around Charleston SC since he was a young lad in the 1960’s as a power boater. Inspired by sailing, Bob became “Captain” Bob in 2006, obtaining a USCG Master Captain License with Sailing and Towing Endorsements. He also holds an American Red Cross Adult and Pediatric First Aid/CPR/AED Certificate. Captain Bob invites you to come aboard and experience the serenity of sailing, take the wheel, trim the sails, or just sit back and enjoy a peaceful tour of the sights and sounds of the historic Charleston Harbor.

Future Captain/Nephew Christian Naples


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.