Nathan Hesse

For Nathan, the love of boats began with his grandparents, fishing in Hatteras Island, kayaking anywhere he could and cruising with his brother and parents on their sailboat on the Chesapeake Bay. As a USCG Captain, US Sailing Instructor and American Sailing instructor, Nathan has worked on sail and powerboats throughout the East Coast, Pacific Northwest, and Caribbean.  

At St. Mary’s College of Maryland, Nathan studied Spanish, but spent much of his time working for the college waterfront or windsurfing. While there, he also landed his first job on a private yacht, sailing on a 7 week cruise from the Chesapeake to New England and back. While in graduate school at the Elliott School of International Affairs at The George Washington University, Nathan worked as the waterfront manager at Eastport Yacht Club. 

After a stint in Maine managing a launch service, Nathan set sail on a schooner bound for Havana, Cuba. Drawn back to his Chesapeake roots, Nathan returned to Maryland and captained the skipjack “Elsworth” and the buyboat “Annie D” for Echo Hill Outdoor School. He also served as the captain of the Chesapeake Bay Foundation’s research and education vessel based in Washington, DC. 

From 2021-2025, Nathan served as the Deputy Director and then Acting Director of the Command & Seamanship Training Squadron at the United States Naval Academy. In this role, Nathan led leadership training aboard 12 Navy 44 sailboats, training instructors and midshipmen to safely sail offshore. He was also instrumental in planning the US Sailing Safety at Sea Seminar held at the academy. 

But Nathan is most at home exploring the water with his wife. Together they’ve explored the marshes and creeks of the Bay in their fishing boat, cruised the Eastern Shore by sail, gunkholed and camped on islands in coastal Maine, and cruised the Adriatic Sea in Croatia. Nathan is excited to share his personal passion for boating, coupled with his experience as an educator to help his clients find the right boat for their adventures, whether they are headed to a local seafood restaurant, a quiet anchorage on the Chesapeake or a far off destination.