
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.

Contact for pricing
Contact for pricing
Contact for pricing
Nestled along the Middle River just north of Baltimore, our location offers a calm and protected environment ideal for learning to sail. The area provides easy access to the Chesapeake Bay, allowing students to gradually expand their skills from the sheltered waters of Middle River to the open bay. Our facilities feature docks and amenities designed to support a comfortable and efficient learning experience, ensuring that students can focus on developing their sailing confidence and techniques in a relaxed setting.
From Baltimore/Washington International Thurgood Marshall Airport (BWI), the most convenient way to reach Starboard Sailing is by car or ride-hailing service. The drive typically takes about 25 to 30 minutes, depending on traffic. Once you arrive, take I-695 North toward Towson, then merge onto MD-702 North (Middle River Road). Follow Middle River Road east for several miles until you reach Red Rose Farm Road; the school is located at 3501 Red Rose Farm Road. If you prefer, you can also rent a car at the airport and drive directly to the school, enjoying the scenic route along the Chesapeake Bay area. Public transportation options are limited for this route, so a taxi, ride-share, or rental car is recommended for the most convenient and efficient journey.
The best time to sail in the Middle River area is from late spring through early fall, typically from late May to early October, when the weather is warm and the winds are steady. Summer weekends are especially popular, offering ideal conditions for both beginners and experienced sailors to enjoy the Chesapeake Bay.
No reviews yet. Be the first to share your experience!
Have you sailed with Starboard Sailing of the Chesapeake LLC?
Log in to leave a reviewSee something wrong or have a question? Message us at hello@sailingtree.com


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.

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.