How to Start Sailing: A Beginner's Guide for Annapolitans
by Tyler Ingle
Annapolis has long been known for its waterfront appeal, drawing sailors, and citizens alike. By the 18th century, the state’s capital became a center for shipbuilding and seafaring, with its economy and culture heavily influenced by life on the water. The U.S. Naval Academy, established in 1845, further cemented the city's maritime legacy by training generations of naval officers and fostering a spirit of nautical excellence. Over time, Annapolis evolved into a haven for both recreational and competitive sailing. With sailing being such a prominent tradition, many locals often want to give it a go. The best way to start is by taking a beginner sailing course through a reputable
sailing school or community program, where you’ll learn the basics of operating a sailboat, understanding wind direction, and handling the sails. Starting on a small, stable boat, such as a dinghy, allows you to grasp the fundamentals in a controlled environment. It’s also important to learn safety practices, knot tying, and how to read weather conditions. “Aboard a boat, people become more than just family — they become a crew who must work together in order to catch the wind and create memories,” said Morgan Bowen, a staff member with The Sailing Academy. “Sailboats offer a unique role for everyone aboard no matter their age or skill level.”
With practice and patience, you’ll not only develop the technical skills but discover the joy and freedom that come with navigating the open water. Fortunately, there are several sailing schools in the area. The best part? For many of them, you don’t even need to own a sailboat. ANNAPOLIS SAILING SCHOOL The country's first adult sailing school, Annapolis Sailing School was established in 1959 by Jerry Wood. Having now opened its arms to youth and adults, this historic sailing school has all the offerings! KidShip Camp is a youth-centered sailing program that allows children to develop the fundamentals of sailing. From beginners to advanced, half-day to full-day, this program has a fleet of eight sailboats for your child to steer. For adults, there are a whole host of courses such as the Basic Sailor Certified Course, all the way up to the Advanced
One of many boats offered for lessons and rentals! Photo courtesy of Morgan Bowen, The Sailing Academy Administrator.
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