SailTime Annapolis Sailing Academy
Annapolis, Maryland, United States
About
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.
Courses (3)
Bareboat Cruising
Contact for pricing
Basic Keelboat Sailing
Contact for pricing
Coastal Cruising
Contact for pricing
Location
The Area
This sailing school is based along Back Creek in Annapolis, just a short sail from the open Chesapeake Bay. The location offers beginners a calm, protected space to get comfortable at the helm, with easy access to wider waters as skills improve. Over the years, the school has helped many new sailors gain confidence on the water. The marina is easy to reach, and its setting makes it a practical and inviting place to learn.
Getting There
If you're flying in, Baltimore/Washington International Thurgood Marshall Airport (BWI) is the closest major airport. From there, it's about a 30 to 40-minute drive to 7082 Bembe Beach Road in Annapolis. Once you're in Annapolis, the sailing school is located at the end of Bembe Beach Road, near the waterfront. It's a straightforward drive from downtown, and there’s parking available on-site. If you're staying nearby, a short taxi or ride-share can get you there without any hassle.
Best Time to Go
In Annapolis, the best time to sail is late spring through early fall, with September often offering the most consistent conditions. The winds tend to settle into a reliable afternoon pattern, and the water stays warm well into October.
Reviews (0)
No reviews yet. Be the first to share your experience!
See something wrong or have a question? Message us at hello@sailingtree.com
More Schools in United States
Starboard Sailing of the Chesapeake LLC
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.
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.
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.