How to Start Sailing in Annapolis: A Beginner’s Guide for Locals

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 also 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 Sailor Certified Course. With two additional cruising courses and private lessons, Annapolis Sailing School makes sailing accessible for those who do not own a boat.

• Annapolis Yacht Club (AYC) – With deep historical roots, this club offers summer programs to both members and non-members. The AYC Junior Sailing Summer Program, for all ages above 5, kicks off its first week on June 9 and runs until August 12. This program starts with the foundations of learning how to sail before progressing into racing, with two race weeks taking place during the course.
  
• J World Annapolis – One of the most popular sailing programs around, this sailing school offers everything from in-person lessons to online seminars and informational meetings that go beyond the boat. J World offers the following courses: Sailing Fundamentals, Performance Sailing, Racing, and Cruising/Liveaboard. They additionally offer US Sailing Certifications and private lessons. Whether you’re taking an entry-level course or are gearing up for a regatta, this sailing school has it all.

• Navy MWR Annapolis – Run by Navy instructors, these sailing and boating classes are also perfect for anyone who does not have access to their own boat. The Basic Keelboat/Skipper “B” sailing qualifying classes are offered. Students can rent the 24-foot Rainbow sailboats after completing the training. By taking and passing the ASA 101 test, students can obtain their American Sailing Association (ASA) 101 Basic Keelboat Certification. These certifications are widely accepted throughout the world, giving youth the ability to use the qualifications worldwide. 

• SailTime Annapolis – An American Sailing Association (ASA) affiliate, this group offers a host of courses with small class sizes, averaging two to four students. Teaching ASA Courses 101-106, SailTime’s instructors are all nationally certified and licensed. Once you have completed your course(s), you may rent boats from SailTime and take them on your own journey.

• The Sailing Academy – Heading out on the Chesapeake Bay, The Sailing Academy provides beginner, intermediate, and advanced courses while providing all your boating needs. The beginner courses last two to four days, with the intermediate spanning from two and a half to five days, and the advanced being anywhere from two to six days. The intermediate and advanced courses may require overnight stays. On the other hand, if you’re just looking to dabble in beginner courses, enjoy lessons from 10:00 am to 4:00 pm each day.

Sailing lessons offer an incredible opportunity to build skills, confidence, and a deep connection with friends and family. Whether you’re looking to explore a new hobby, improve your sailing technique, or prepare for competitive racing, these lessons provide a structured and supportive environment for learning. 

With the wind in your sails and endless horizons ahead, you’ll gain not only the ability to navigate the waters but also a sense of freedom and adventure that stays with you long after the lessons end.

View this article in our quarterly magazine, The Motherlode.