Meet Your Captains

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.

Holding a 100-ton Masters license, Joe has been sailing monohulls and Catamarans for 30 plus years and a ASA instructor for the past 15, teaching 101, 103, 104, 105, 106, 114.

On a cold winter day in Chicago, a matinee viewing of “Captain Ron” became a catalyst for a major change in his life direction. Being disenchanted with the music industry and its lifestyle he packed up his truck and headed to Florida and began working in boat yards, learning from “old salts” while acquiring sea time and gaining experience. Upon earning his Captain license he began working as a tugboat operator until suffering a broken back due to a crane mishap.

While recovering he began reading sailing books and vowed to return to the sea on a sailboat. After years of rehab he traded in his walker for a 32 foot Bayfield cutter and took ASA 101, 103, 104, then departed on a five year sabbatical single-handed through the Bahamas and Caribbean.

He has worked as a delivery captain from Annapolis Maryland to Florida Keys, Bahamas and beyond with more than 50 Gulf Stream crossings

As an ASA instructor, his hands on teaching approach is laid back, stress free and entertaining. He has been the lead instructor in Abaco Bahamas for the past 10 years helping future adventurers achieve their sailing dreams. He has organized flotillas and regattas and was named an ASA Outstanding instructor 4 times.

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.

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.

Captain Amy holds a USCG Master’s 25 GT license with sailing endorsement and enjoys sailing on the Chesapeake Bay, her home waters. She is an ASA Instructor for ASA 101, 103, 104, 105, 114 and 118 and has certified 175 students in the past five years. She also is a qualified offshore skipper for the Naval Academy Command and Seamanship Training Squadron. Beyond her volunteer activities, and when not on her own Wauquiez 40, she loves coaching new sailors, and especially sharing the tips and tricks of a catamaran.

Captain Matt Dolby started his passion for the sea at a young age. Coming from a multiple generation of sailors, he has sailed all along the east coast, Bahamas and the Caribbean and has also owned several sailboats in his life. He also developed a passion for fishing, which pointed him in the direction of becoming a classically trained sushi chef. First a chef and now a well-seasoned captain in the Florida Keys, Captain Dolby brings his conscientious work ethic and hospitality to welcome all our guests on board. He is always looking forward to meeting new people and taking them on new adventures, teaching and sharing knowledge, swapping stories, exploring the underwater world, eating the freshest catches after a day of fishing, and sailing towards sunsets. He will be happy to discuss your sailing trip itinerary and menu preferences. Their bright personalities and attentiveness will make you feel right at home and relaxed on board.

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 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.

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!