About Us

What kind of school are we?

So what do we define as a successful sailing course? In order of priority: safety, fun, and learning. Generally, there are two kinds of sailors – racers and cruisers. We are not a racing school. Our education focuses more on safety and cruising. This does not mean we will not teach you how to get your boat to go fast, we simply do not prioritize it. The course is successful to us if you learned how to safely operate a boat and had a great time doing it.


Why do we do it better than anyone else. Why trust us?

Instructor : Student ratio

We have the lowest guaranteed student to instructor ratio around. That means you get more tiller time and more bang for your buck.

Specialized boats

The Rainbow 24’ is the best boat around for basic sailing instruction. The Annapolis Sailing School, in coordination with famous boat designers Sparkman & Stephens, built it specifically for that purpose. Being the first in the industry has its benefits.

An unbeatable location

Not only are we located in the sailing capital of the country, just a little over 2 miles from downtown, but we also have the best spot in Annapolis. Located at the mouth of Back Creek, our marina is protected from the elements, but doesn’t require a lengthy motor to get out into open water. With no long creeks to navigate, students, renters, and members are quickly on the Chesapeake Bay.

The longest record of teaching sailing

Before there was the American Sailing Association, before there was U.S Sailing, before there were charter companies, there was the Annapolis Sailing School. Established in 1959, we have had a lot of opportunities to learn from our students. With this knowledge we have established what is known as ‘The Annapolis Way’ of teaching sailing. Now without giving up too much of the secret, The Annapolis Way maximizes hands-on, on-the-water instruction, while providing students the necessary amount of theory.

This allows students to learn skills physically while also giving students the theoretical basis to continue to learn on their own. We will be the first to say we can’t teach you everything about sailing, but we will provide you with the foundation on which you can continue to grow your sailing skills safely.

Still want to know more about the Annapolis Sailing School? Feel free to contact us to speak with one of our knowledgeable staff.