The Sailing Academy at the Annapolis Boat Show 2026

⛵ Sailing School Spotlight: The Sailing Academy (@thesailingacademy) Meet the team from The Sailing Academy! We caught up with them at the Annapolis Sailboat Show to learn about their cruising-focused sailing programs and how they’ve helped sailors build confidence on the water for over two decades. 🌊 What makes The Sailing Academy special? What began as a sailboat club in the early 2000s has grown into an American Sailing school dedicated to preparing confident cruising sailors. Located in Deale, Maryland, on the Chesapeake Bay, they offer hands-on instruction and a sailing club with boats ranging from 25 to 50 feet. ⛵ What’s one thing people might not expect about training with you? Students learn aboard actual cruising sailboats! Instead of small dinghies, training begins on 30-foot boats equipped with wheel steering, inboard diesel engines, and spacious cockpits, helping students develop practical skills for future charters and cruising adventures. 📍 What makes the Chesapeake Bay a great place to learn? The Sailing Academy focuses on preparing students to confidently take the helm and explore independently. Their cruising-oriented instruction gives sailors the skills and experience to continue their journey beyond certification. 🎟️ What’s your favorite part of the Annapolis Sailboat Show? For The Sailing Academy, it’s like a homecoming! After exhibiting for approximately 25 years, the team loves reconnecting with former students who have gone on to own boats, charter, race, and even teach sailing. ⚓ How can someone get started? Visit thesailingacademy.com or stop by Dock A1 at the Annapolis Sailboat Show to learn more about their sailing courses and club! #AmericanSailing #TheSailingAcademy #AnnapolisSailboatShow #LearnToSail #SailingSchool #ChesapeakeBay #SailingLife