Annapolis Sailing School

★★★★★Christopher Smith

I recently completed ASA 104 (took ASA101, and 103 last year) with Annapolis Sailing School and was very impressed. The instructors demonstrated exceptional knowledge and a passion for sailing, paired with remarkable patience. They created a supportive learning environment and expertly explained concepts, always taking the time to answer questions. Importantly, Annapolis Sailing School prioritizes getting you on the water quickly – the focus on practical application was invaluable and I felt confident sailing very soon. I highly recommend Annapolis Sailing School to anyone looking to learn to sail for any age. They provide a great educational experience focused on practical skills.

★★★★★Doug Smith

My wife and I took ASA 101 and ASA 102 through the school in Oct 2024. We have “some” sailing experience, but felt like it was time to get the certificates. The school is conveniently located, and the staff is very friendly. (Who wouldn’t be friendly if your job is sailing every day?). They have a large fleet of Rainbow 24’s and they are in pretty good repair (def better than average for rental boats). Staff is quick to attend to anything that needs something. We sailed a Tartan 27 for the 102 class, and it is very well laid out. My wife is an experienced sailor on dinghies, but she didn’t feel like we would be able to manage a 25’ + boat on our own. After going through the classes together, we feel very confident that we could sail in reasonable conditions (which is exactly what the class description promises, so WELL DONE!) For the 101 class, we had Andy as our instructor, and we had Jonah for the 102 class. Andy is very thorough and explains everything very clearly, before we go do it. He was patient and provided both corrective coaching as needed and also called out when you were doing something well, which was fantastic. Particularly helpful was running very realistic man-overboard drills in higher wind conditions, since that is one of the worst things one might face on a vessel. He was also particularly calm and patient with a member of our class who was struggling with mastering the physical skills. Jonah is also a solid coach. He’s much more of an intuitive sailor compared to Andy (i.e. quick to change tactics as the conditions shift). He clearly has a lot of race experience, which was great for the 102 class, where the focus was more on sail trim and maximizing boat performance. Under his watchful eye, I was able to get comfortable putting up and pulling down a spinnaker on my own, with just my wife at the helm. (I sure didn’t think that was going to be a skill I’d acquire this week). My only ‘complaint’ about the week was that the 102 exam was poorly done. This isn’t the school’s fault- the American Sailing Association writes the exams. Jonah was fair, though, and willing to field questions about how the exam was worded, etc. (My wife passed with an 80. I didn’t pass the 102 exam) I came into the week thinking “meh, how hard can this be? I’ve done a lot of this stuff before”. I’m *really* glad we took the classes, and I expect we’ll be back for more.

★★★★★RAL Liz

What a great experience! This was the 103, Coastal Cruising course and Paul was a fabulous instructor that took his time and we really felt proficient by the end of the course. The whole course is taught on the water on a beautiful 37’ Beneteau Oceanis. Just going out was such a joy that you barely realize you’re in a class! There were only 3 students plus the instructor so very heads on and personal attention. I feel confident now to go out and sail any costal cruiser from 30-39’ on the Bay. Thanks Paul and thanks Annapolis Sailing School!

★★★★★Caitlin Trasande

What a refreshing break from the urban grind! While visiting from NYC my son enrolled in the teen basic sailing and advanced sailing courses. New skills (always good to be handy on a boat), new friends, chill young adult instructors, gorgeous water. Pitch perfect introduction to sailing! ⛵️⛵️⛵️⛵️⛵️⛵️⛵️

★★★★★J Kosmides

Great experience this week at the school earning my ASA 101 keel boat cert. All of the instructors were highly experienced and they took the time to answer every question that was asked. We had a great time on the water and everyone had a ton of hands on sailing time. The time spent in the classroom, rigging the boats and sailing has added tremendously to my knowledge and confidence.