Chronic Sailing
Annapolis, Maryland, United States
About
Chronic Sailing is a well-regarded Annapolis-based sailing school, charter company, and yacht management service that specializes in catamaran sailing, cruising, and offshore passage-making. Located on Bembe Beach Road, the school offers a hands-on learning experience through ASA-certified courses designed for both beginners and experienced sailors. With a focus on seamanship, safety, and offshore readiness, students gain the skills and confidence needed for coastal cruising and long-distance voyages. Led by Shawn Owen, whose offshore experience includes an Atlantic crossing with the Clipper Race, the school provides personalized instruction on liveaboard multihulls, covering essential skills like twin-engine maneuvering, reefing, anchoring, and passagemaking. In addition to training, Chronic Sailing offers private charters on Chesapeake Bay, blending adventure and comfort for day sails, sunset cruises, and overnight trips on fully equipped catamarans.
Courses (3)
Basic Keelboat Sailing
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Coastal Cruising
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Bareboat Cruising
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The Area
Located in Annapolis, Maryland, Chronic Sailing offers a comprehensive sailing education on the Chesapeake Bay. The area provides ideal conditions for learning, with sheltered waters, consistent winds, and scenic surroundings that enhance both beginner and advanced training. Students benefit from hands-on experience aboard well-maintained vessels, gaining confidence in seamanship, navigation, and boat handling. Whether starting out or refining skills for offshore passages, the school's location allows for practical, real-world sailing in a setting renowned for its maritime heritage.
Getting There
To reach Chronic Sailing in Annapolis, start by flying into Baltimore/Washington International Thurgood Marshall Airport (BWI), approximately 30 miles north of Annapolis. From the airport, you can rent a car or use a ride-hailing service like Uber or Lyft for a convenient 45-minute drive south to the school located at 7082 Bembe Beach Road, Suite 204. If you prefer train travel, Amtrak services the nearby BWI Rail Station, where you can transfer to a taxi or rideshare for the short trip to Annapolis. Once in Annapolis, the school is easily accessible by car or taxi from major hotels and the downtown area.
Best Time to Go
The best time to sail in Annapolis is from late spring through early fall, with warm temperatures and generally calm conditions making it ideal for both day trips and longer passages. Early mornings and late afternoons tend to offer the most comfortable sailing conditions, especially before the summer heat settles in.
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