





, 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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21220, USA
Starboard Sailing is located just north of Baltimore on the Middle River, offering a peaceful and protected setting ideal for both beginners and experienced sailors. The school's fleet consists of cruising sailboats similar to those used worldwide, featuring large, stable cockpits and comfortable cabins. Fully equipped with wheel steering, inboard diesel engines, and electronics, these boats are well maintained to ensure a safe and enjoyable sailing experience. The calm waters of Middle River provide a perfect environment for learning, while just a short sail away lies the Chesapeake Bay for practicing more advanced skills.

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.
Rock Hall, Maryland, United States
Delmarva Sailing School is located in Rock Hall, Maryland, offering a variety of sailing courses suitable for all skill levels. Since 2008, the school has been dedicated to providing engaging, well-structured instruction in a relaxed setting, with lessons often taking students to scenic destinations along the Chesapeake Bay. Their team of certified instructors emphasizes hands-on learning in real sailing environments, helping students gain confidence and skills efficiently. Small class sizes and a comprehensive curriculum make it a popular choice for those looking to start or advance their sailing journey.