Chronic Sailing is a premier Annapolis-based sailing school, charter company and yacht management services, specializing in catamaran sailing, cruising, and passage-making. . As an American Sailing Association (ASA) certified school, Chronic Sailing offers a structured and hands-on approach to learning, with courses designed for both beginners and experienced sailors looking to refine their skills. The school places a strong emphasis on seamanship, safety, and offshore preparedness, ensuring that students develop the confidence to handle everything from coastal cruising to long-distance passagemaking. Whether you’re looking to charter your own catamaran, plan a liveaboard adventure, or prepare for an offshore voyage, Chronic Sailing provides the expertise and training to make it happen.

At the helm of Chronic Sailing is Shawn Owen, the school’s owner and lead instructor, whose sailing experience spans more than 30,000 offshore nautical miles, including an Atlantic crossing with the Clipper Round the World Race. His extensive offshore and passagemaking background, particularly in multihulls and cruising vessels, makes him a highly sought-after instructor in the Annapolis sailing community. Shawn’s real-world expertise brings invaluable insight to his courses, as he teaches students how to handle the unique challenges of catamaran sailing, from docking and sail trim to offshore passage planning. His hands-on teaching style ensures that students not only master the mechanics of sailing but also develop the decision-making skills and seamanship required for extended cruising and open-ocean voyages.

Beyond instruction, Chronic Sailing specializes in private catamaran charters, offering luxury sailing experiences on the Chesapeake Bay. Guests can enjoy day sails, sunset cruises, and overnight excursions aboard fully equipped, well-maintained cruising catamarans. Each charter is designed to blend adventure with comfort, allowing guests to explore the water at their own pace, whether guided by an expert captain or taking the helm themselves. Chronic Sailing also provides customized training for those interested in bareboat chartering or transitioning to a liveaboard lifestyle, ensuring that clients leave with the skills and confidence to sail independently.

What sets Chronic Sailing apart is its dedication to catamaran training and offshore cruising education. The school maintains a low student-to-instructor ratio, ensuring each participant receives personalized instruction on liveaboard multihulls. The curriculum covers essential skills such as twin-engine maneuvering, reefing systems, anchoring techniques, and passagemaking strategies, preparing students for extended voyages. With Shawn Owen’s leadership and extensive offshore experience, Chronic Sailing is not just a sailing school—it’s a launchpad for sailors looking to explore the world by catamaran. Whether you’re earning your ASA certification, planning your first offshore passage, or simply looking to enjoy a luxury catamaran cruise, Chronic Sailing delivers an unparalleled experience tailored to those who dream of life on the water.