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.

Captain Chris Staley

Chris Staley

Chris is a licensed coast guard captain with 100 ton master with sailing and commercial towing endorsements. He has been an ASA instructor since 2007 and is certified to teach ASA 101, 103, 104, 105, 114, 118, and 119. Chris is a life-long sailor with experience sailing dinghies, beach catamarans, racers, cruisers, and cruising catamarans. He also has captained fishing charters and operates commercial marine assistance vessels.

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.

Captain Britt Baker

Britt Baker

Captain Britt holds a USCG 100 Ton Master license with sailing and towing endorsements and is also a American Sailing Association level 101, 103, 104, and 114 certified instructor. He has spent most of his free time pursuing the “magic” of sailing in many different types of racing dinghies, windsurfing, and kiteboarding. In 2017 he stepped away from his photography career, sold his camera stores, and moved aboard the Green Eyed Lady, a Seawind Catamaran, to “live the dream”! Britt is available as a sailing instructor, captain, and delivery captain. Feel free to contact Britt at or 1-814-935-4862 by phone, text or WhatsApp.

Captain Brad Pasmore

Brad Pasmore

Captain Brad holds a USCG 50 Ton Masters License with Sailing and Towing endorsements. He has been around and on the water his entire life. Brad spent the last 2 years sailing catamarans in the Florida Keys and Chesapeake Bay as well as delivering catamarans up and down the east coast. He also has 3 years experience sailing a 45 ft monohull in and around the Gulf of Mexico. Brad is a fun-loving water-sport enthusiast, he is frequently found scuba diving, windsurfing, fishing, kiteboarding, and of course, sailing.

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 Dave Lamay

Dave Lamay

Growing up on the waters of the Chesapeake Bay and Potomac as well as living in the Bahamas and Caribbean, Capt. Dave brings a broad range of experience from dive boats to tall ships. Adding to this a USCG 100-ton Masters license with sailing and towing endorsements. In addition, Capt. Dave is a musician and photographer and a former scuba Instructor. He looks forward to showing you a good time on the water!

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