Meet Your Captains

These are bareboat charters and therefore you are always welcome to provide your own captain (satisfactory sailing resume and short sea trial prior to charter required). If you need help finding a captain for your trip you are welcome to choose from one of the captains below who are pre- approved to operate catamarans.

Shawn Owen

Captain Shawn holds a USCG 50Ton Near Coastal Master License with sailing endorsement. Shawn has captained regularly on the Chesapeake Bay for the past 3 years, as well as captained and crewed multiple deliveries to and from Florida, the Bahamas and the Caribbean. Shawn is a current ASA Certified Instructor for 101-106 and 114. He offers private sailing instruction and is the instructor for the Sailing Seminars. He is also a professional local musician so inquire about having him perform a few songs aboard your cruise! Please feel free to contact him directly at and (443) 995-4642.

Steve Coffman

Broker, Charters, Deliveries. A life long Chesapeake Bay waterman holding a USCG Masters 25T captains license. Growing up on the bay Steve has an intimate knowledge of the Chesapeake and it’s tributaries, always able to find the right spot for any occasion. You may hear him say “everything is better on the bay”. Blue water experience in the Caribbean, Gulf of Mexico, Atlantic and Pacific on both power and sailing vessels from kayaks to the big cats. Contact him directly at 301-509-4376 for all your boating needs and questions.

Captain Adam Yearwood

Adam Yearwood

Captain Yearwood is a licensed United States Coast Guard captain with extensive experience operating sail and power vessels of all sizes including harbor tugs and large ships. He holds a 1,600 ton Master’s license and a second mate unlimited tonnage license. Having grown up on power boats and competitively raced on small and medium size sailboats, including historic Chesapeake log canoes, he is an expert boat handler with exceptional seamanship skills. Captain Yearwood has sailed across the Pacific and Atlantic Oceans, Gulf of Mexico, Caribbean, China Sea, Mediterranean Sea, and North Sea, and the East Coast of the U.S. including the Chesapeake Bay. As a charter boat captain, he enjoys meeting new people and providing clients with a fantastic experience on the water. With a passion for sharing knowledge, he lectures on maritime topics, provides private hands-on vessel operation instruction and delivery services, and is member of the United States Coast Guard Auxiliary instructing boater education courses including the Maryland state course.

Captain Jesse Winter

Jesse Iliff

Captain Jesse is a born and bred Chesapeake “river rat”. He has spent countless happy days every summer exploring the rivers of the Bay on a host of power and sailing vessels and has raced both competitively. Jesse works on and for the rivers of the Chesapeake every day. In addition to holding a USCG 50 ton Masters Credential, Jesse is an environmental lawyer and your South Riverkeeper since 2015. Jesse is a student of all things Chesapeake, and always happy to chat about the history, law, science, and economics of the Bay. When he isn’t working on the water, he is likely to be playing there–kayaking, fishing, and exploring with his wife Abbey and their two children.

Captain Britt Baker

Britt Baker

Britt carries a USCG 25 Ton Master Captain’s License with Sailing and Towing Endorsement. For more than 30 years, Britt has sailed extensively through the Carribbean, Florida Keys, and up and down the east coast of the United States. Britt is an experienced delivery captain, sailboat racer, avid diver, and wind surfer.

Captain Rob Maher

Rob Maher

At the age of 12, my family and another pooled funds and bought a 32′ wooden, single screw Luhrs flybridge convertible. Docked at Castle Marina on Kent Island, MD in the early ’70’s, our mornings were spent in awe of the wildlife traversing the narrows and days cruising the Bay. In no time I was hooked and gaining experience crewing on racing boats. My first boat was bought a year out of college and the fleet has grown since then. Boats I’ve owned include: Hatteras 43 MY (present), 44′ Fountaine Pajot sailing cat (present), 25′ Robalo CC (present), 21′ Hurricane, Morgan 43, Hatteras 38 conv., Catalina 34, Buccaneer 27, Venture 224. And those I’ve operated include: 75 Hatteras MY, 61 Hatteras MY, Ocean 56, Hatteras 50 Sportfish, Irwin 37, Contest 32, C&C 40, CSY 44, Sea Ray 50, C&C 32, Limestone 25, Silverton 40. I was fortunate to have spent my 20’s ferrying boats up and down the US east coast, Bahamas and into the Caribbean. (While preferring the expediency of running outside, I know too well the ICW and its many ports). Home has always been the Chesapeake Bay and though I’ve still not seen all that Capt. John Smith explored, I’ve experienced much of it and am thrilled to share the many great experiences the Bay offers!

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