





Grasonville, Maryland, United States
R&R Charters and Sail School is a Chesapeake Bay-based ASA-certified sailing school, proudly named the 2010 ASA Sailing School of the Year. Owned and operated by David and Penelope Renoll—both USCG-licensed captains with over 35 years of sailing experience on the Chesapeake Bay—the school brings together a deep love of sailing and a passion for teaching. The Renolls have also sailed internationally in Greece, Italy, the British Virgin Islands, St. Martin, and Bermuda, infusing their instruction with real-world experience and a spirit of adventure. With a strong foundation in professional education, R&R offers a highly personalized learning environment. Students can choose to learn individually or in small groups of up to four per boat, ensuring maximum hands-on time at the helm. Whether you're a complete beginner or looking to sharpen your skills, the focus is on building confidence and competence in a fun, supportive setting.

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Annapolis, Maryland, United States
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.

Solomons, Maryland, United States
Sail Solomons is a well-established sailing school located in the charming town of Solomons, Maryland. Known for its friendly atmosphere and top-notch instruction, the school offers a range of courses and training programs suitable for all levels, from beginners to experienced sailors. With a focus on personalized attention and quality sailing experiences, Sail Solomons provides students with the skills and confidence needed to enjoy the water safely and comfortably.

Havre de Grace, Maryland, United States
BaySail is located at the top of the Chesapeake Bay in historic Havre de Grace, Maryland. The harbor offers protected waters and steady winds, making it an ideal spot for learning. The school features two classrooms, a marine store, and is surrounded by charming bed and breakfasts, shops, and restaurants along Washington Street. With a focus on hands-on instruction, BaySail provides scheduled small classes and private lessons on their boats or clients' vessels, catering to sailors of all levels.