Sailing Schools in Maryland
12 search results
R&R Charters and Sail School
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.
Chronic Sailing
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.
Sail Solomons
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.
Sail Away Catamarans
Edgewater, Maryland, United States
Sail Away Catamarans is located in Edgewater, Maryland, offering a laid-back yet professional approach to sailing education. They operate modern, well-maintained catamarans ranging from 38 to 50 feet, providing customized live-aboard training sessions in the Bahamas, Key West, and the Chesapeake Bay. Their team of ASA-certified and US Coast Guard Licensed Instructors bring years of cruising, racing, and chartering experience, ensuring students learn in a safe and engaging environment. The school emphasizes fun and safety while helping students gain confidence and skills through structured certification programs.
SailTime Annapolis Sailing Academy
Annapolis, Maryland, United States
SailTime Annapolis runs a laid-back but serious sailing school out of Horn Point Harbor Marina, right where Back Creek meets the Chesapeake. You don't have to be a SailTime member to take lessons here, and classes stay small—usually just two or three people on the boat. They’ve got a solid range of courses, whether you’re new to sailing or looking to sharpen your skills. Beginners start on Beneteau First 22s, and more advanced students train on newer Hunter monohulls and Gemini catamarans. Lessons are hands-on, taught by experienced instructors, and scheduled to fit around your life.
Starboard Sailing of the Chesapeake LLC
Middle River, Maryland, United States
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.
Gratitude Sailing Institute
Essex, Maryland, United States
Located on the peaceful shores of Chesapeake Bay at Markleys Marina north of Baltimore, the Gratitude Sailing Institute offers a comprehensive sailing experience. The school’s boats are maintained to the highest maritime standards, and classes often take place in a liveaboard environment, giving students a taste of life at sea. The curriculum is led by U.S. Coast Guard Licensed Master Captains who emphasize safety, education, and enjoyment, helping students develop essential seamanship skills and confidence on the water.
BaySail School of Sailing
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.
Navy Patuxent Sailing Club
Patuxent River, MARYLAND, United States
The Navy Patuxent Sailing Club is made up of over two hundred members, including Active Duty, Reserve, Civil Service, and Contractor personnel. They come from diverse backgrounds but share a common passion for sailing. Located near the Patuxent River and Chesapeake Bay, members enjoy some of the best sailing on the East Coast just minutes from their base. The club aims to give eligible personnel and their families the opportunity to experience and enjoy sailing, improve their skills in handling both small and large boats, and promote sailing as a sport within the Navy. Members also participate in small boat racing, develop seamanship skills, and engage in water safety activities, all while fostering camaraderie and supporting morale and recreation efforts.
Maryland School of Sailing
Rock Hall, Maryland, United States
The Maryland School of Sailing and Seamanship is dedicated to helping people become skilled and confident sailors. Located at Lankford Bay Marina in Rock Hall, Maryland, the school offers comprehensive sailing courses taught aboard rugged Island Packet cruising yachts by experienced Coast Guard Licensed Captains. Their programs focus on building a solid foundation of sailing skills, emphasizing safety and mastery over shortcuts. From full-length live-aboard beginner courses to advanced navigation classes, the school caters to sailors at all levels and encourages hands-on learning, often allowing students to stay aboard the yachts throughout their courses for a true immersive experience.
Delmarva Sailing School
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.
Waypoints Annapolis
Annapolis, Maryland, United States
Waypoints Annapolis is located at 222 Severn Avenue, in Building 15 Suite 36. Nestled in the charming city of Annapolis, Maryland, the school offers a relaxed and welcoming environment for sailors of all levels. Whether you're just starting out or looking to hone your skills, the friendly atmosphere makes learning to sail an enjoyable experience.