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About Us

Why Learn From Us?

The Sailing Academy has been introducing people to sailing for many years. Our teaching method is more like on the water coaching than simply taking a class. The reason for this is simple; we started out as a Sailboat Club, not a school. Our goal was to coach new sailors to become proficient and confident so they could take our sailboats out on their own.

Even though we have been an official American Sailing Association affiliate school since 2002, our instruction was only available to club members. In the spring of 2008, we started offering courses to the general public at Herrington Harbour Marina. You no longer need to be a member to take advantage of our unique instruction style!

Sail right on the Chesapeake Bay. Our marina has direct access to the Chesapeake which is wide open water with no narrow rivers or strong currents to deal with. That means plenty of great wind and very little traffic from other boats.

Ditch the Stick! You will start out on a yacht with wheel steering. There are two ways to steer a sailboat, with a wheel or a tiller (a long stick attached to the rudder). All modern cruising sailboats have wheel steering, that’s why we start all our beginning students on boats with wheels. We are a sailing school that focuses on cruising.

wheel of a sailboat


no tiller image









We Are Centrally Located

We are centrally located on the western shore of the Chesapeake Bay at Herrington Harbour Marina. If you are coming from Northern Virginia or Washington DC you will find Herrington Harbour the closest marina on the Chesapeake. We are just south of Annapolis, so we do not sail in the crowded Annapolis Harbour. From our location, destinations such as Baltimore, St. Michaels, Annapolis, Galesville, and Solomons are all within a day sail.


We Are Cruising Focused

The Sailing Academy was started by cruising sailors. A “cruiser” is someone who enjoys exploring new destinations while traveling by sailboat. Although they may enjoy racing around the buoys once in a while, they are more interested in relaxed sailing with friends and family. Our goal is to prepare you for such experiences.

It doesn’t matter if your goal is to simply to cruise the Chesapeake Bay or to eventually cross oceans, The Sailing Academy is a great place to start. Many of our instructors have bluewater experience and have much more to offer than just the sailing curriculum.


We Provide Options to Keep You Sailing

After you complete a course, time is needed to practice the new skills acquired. The more time you have on the water, the more naturally you execute sailing procedures. Your confidence grows as the skills become second nature.

Although we are not a “boat rental” facility, we do make our boats available to students. You may charter a sailboat for a day, or join the Sailboat Club to have regular access to our fleet. As you progress, you can move up to larger boats. A majority of our former members have gone on to own their own boats.