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
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Basic Keelboat Sailing
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Coastal Cruising
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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.
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