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 Jennifer McQuilken


Captain Jennifer McQuilken had her sea legs before her land legs. She grew up sailing, fishing, and swimming in Long Island Sound wither her family and got her recreational boating license before even having a driver’s license. A walk along the beach, even in the dead of winter, was always full of wonder. She had no fear of picking up sea creatures and smelly things that washed up along the beach. She spent her summer teaching swimming lessons in Niantic Bay and volunteering at Mystic Aquarium.

The cold drove her south, where she went to school at Florida Tech, studying marine biology and earning a degree in communications. She jokes that after college she ended up in the Washington, D.C. area by mistake, but quickly hit her stride. She managed client relations for one of the top advertising agencies in the DC area and was the brand and marketing manager for McGruff the Crime Dog. Never one to give up the wind, she found the nearest ocean and traveled up and down the east coast on weekends racing Hobie Cats.

Missing living in a land of salt water and afternoon sea breeze, she moved to Charleston in 2007. Alternating time between her communications consulting and working as a tour guide, she founded Charleston Coastal Charters. One of her boats, Horizon Seeker, was the first boat to be featured as a vacation rental on Airbnb. She sailed with friends, fished the creeks and reefs, and volunteered with the U.S. Coast Guard Auxiliary. She now has her near coastal operator of uninspected passenger vessels (OUPV) captain’s license and now splits her time between the boats and her marketing career.

Jen loves sharing the history and ecological wonders that make the Low-country the special place that it is. Whether it is chatting about the local dolphins, explain how a pelican catches it fish, or pointing out some of the world class architecture, you are sure to enjoy your time on the boat with her.

When she is not on Mental Heeling, just follow the winds and tides and you’ll find her somewhere in the marshes of Charleston, often kayaking, paddle boarding, or fishing. Even with all she has on her plate, Jen still finds time to volunteer at Cape Romain National Wildlife Refuge saving baby sea turtles.

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.