Sailing Certification & Training with Starboard Sailing in Maryland

Middle River, Maryland, offers a prime setting for getting on the water, and Starboard Sailing stands out as the go-to school for mastering the art of catamaran and coastal cruising. Located on the Chesapeake Bay’s sheltered waters, the school provides a comprehensive path for sailors at all levels—from beginners working through ASA 101 Basic Sailing and Coastal Cruising classes to advanced captains pursuing instructor qualifications or bareboat charter endorsements.

Starboard Sailing’s offerings cover essential and specialized skills, including ASA 114 Cruising Catamaran certification, ASA 104/114/IPC Bareboat Chartering, and the often challenging ASA 118 Docking class. The rare combination of classroom instruction and hands-on practice ensures students don’t just learn the theory but gain confidence behind the helm, an approach validated by glowing reviews highlighting Captain Jerry’s thorough and patient teaching style. Many students find his pragmatic methods transformational, building skills that go beyond the syllabus to real-world seamanship.

Middle River’s gently tidal environment, shielded in parts by barrier islands and estuary channels, creates an ideal training ground for coastal cruising techniques. Here, sailors hone boat handling, navigation, docking, and weather reading skills without the stress of open ocean waves. This makes the location a unique hub in Maryland’s sailing scene—offering both access to the expansive Chesapeake and protection for those still perfecting their craft.

Whether aiming to charter a sailing catamaran on summer vacations or preparing for the demands of coastal cruising, Starboard Sailing’s well-maintained fleet and expert instruction provide unmatched value. For locals and visitors alike, this school offers an invitation to develop expertise with a reputable institution that’s become a trusted presence in Maryland’s outdoor adventure and sailing community.