Annapolis Sailing School
Annapolis Sailing School
5
9:00 AM - 4:30 PM
Monday
9:00 AM - 4:30 PM
Tuesday
9:00 AM - 4:30 PM
Wednesday
9:00 AM - 4:30 PM
Thursday
9:00 AM - 4:30 PM
Friday
9:00 AM - 4:30 PM
Saturday
9:00 AM - 4:30 PM
Sunday
9:00 AM - 4:30 PM
About
Learn to sail with America's first sailing school in beautiful Annapolis, Maryland! Our family-owned sailing school prides itself on being able to teach anyone how to sail the Annapolis Way - fun and relaxing. From introductory sailing experiences to getting your ASA certifications, we offer something for everyone. Call us today to learn more! Offerings: ASA 101, 103 and 104 Certifications, Basic Sailing Courses (2 days), 2 hour Evening Sail Cruises on Beneteau 37s, Private and Family Sailing Lessons, Rainbow 24 Sailboat Rentals, Summer Kids' Programs, And More!
Annapolis, Maryland

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Travelers talk about
(14 reviews)
(3 reviews)
(2 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles116 reviews
Excellent
113
Very good
2
Average
0
Poor
1
Terrible
1

441jpd
Washington DC, DC24 contributions
5.0 of 5 bubbles
May 2022
This was an awesome adventure that combined detailed curriculum with a fun and inclusive learning experience. The Annapolis Sailing School community, location and environment is very welcoming and inclusive; making it a great choice for people of all ages, backgrounds and interests. We had 11 in our class and enjoyed input and expertise from more than 5 hands-on instructors. The 3 day beginner's course (101) educated me (and 2 others on our boat who became new friends/crew) on the techniques, skills and nuances of sailing. Plan to spend about 4 hours in a classroom setting over the 3 days and the rest of the time you're on the docks and out on the water. Art, our instructor on the boat, was the ideal teacher who patiently allowed us to take the helm and connected new vocabulary, techniques and safety issues from the printed course material into real-time practice. I'd recommend this to anyone looking for a great sailing foundation and will definitely be back to take the more advanced courses.
Written June 1, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

CatheH
Herndon, VA19 contributions
5.0 of 5 bubbles
Jun 2021
John Cosby delivered masterful private 2-day training, even tho' there was zero wind both days! Although the sailing experience of the three students spanned a wide range, John made the most of every hour by inquiring what each wanted to learn and then tailoring the lesson to meet all of the knowledge levels. We learned about the basics of a sailboat, the navigation markers, right-of-way scenarios, maximizing the power of wind directions, and conquering the intimidation of docking. John simplified terms and used examples, humor metaphors, and experiential learning to help us to commit the learning to memory. The biggest value to all 3 of we students was demonstrating and practicing the ability to slow down any maneuver to gain control, confidence, and calm as a sailor. As a novice sailor, I now have faith in my knowledge and ability to drive the boat safely and also to be able to relax and have fun. I plan to take a future class with Annapolis Sailing School to apply this foundation of boating under motor and sailing safety basics to sailing by harnessing the wind. I highly recommend this school to any sailor of any level of experience!
Written June 13, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Kyra M
Glen Burnie, MD1 contribution
5.0 of 5 bubbles
Jul 2021 • Couples
I’ve taken other sailing lessons, but after taking the 101 course, I feel like I’m finally on my way to understanding sailing. Gibing and broad reaches and donuts are no longer foreign concepts. We were very fortunate to have Phill S our instructor on our boat. 16 mph and then 12 mph winds the next day made it thrilling, not scary, because you also learn Rainbows ( the sailboat) don’t tip over. Highly recommend the School and Phil!
Written August 17, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Bill Colbert
2 contributions
5.0 of 5 bubbles
Jul 2020
I took 2 courses over 5 days with 3 instructors. It was not only a great learning experience but also a very fun time. I am looking forward to taking more courses from Annapolis Sailing School to increase my sailing knowledge and skills. I couldn't recommend the school any higher. Great people, great content and great boats.
Written July 24, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

jpettey2016
Annapolis, MD17 contributions
5.0 of 5 bubbles
Aug 2021
This weekend I took ASA103 at Annapolis Sailing School and had a terrific experience. Our instructor was John Cosby who can teach many of the courses the school offers. My colleagues Patrick and Michael were fortunate to have John as our instructor. He has a tremendous amount of experience which he shared with us both on the boat and in the classroom.
This is not the only course I've taken as Annapolis Sailing School and I have sailed there dozens of times. I highly recommend you visit them for a half-day of sailing one of their rental Rainbows and then a beer on the beach remembering your day.
Thanks again John!
Written August 15, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Ken Cascio
1 contribution
5.0 of 5 bubbles
Oct 2020
Amazing location and a great group of people and boats. I had an excellent week during my ASA 101 Complete Sailor program. Thumbs up to Phil, Art, and Tom! I would recommend the Complete Sailor version over just the ASA 101 Certification - you get to sail on the larger boats for the last two days which gives you a great prep to 103/104.
Written October 11, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks for your kind words, as you pointed out it is the people who make the difference! We love ours.
Written October 12, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Mary Anderson
Annapolis, MD6 contributions
5.0 of 5 bubbles
Jun 2021 • Friends
If “the sea’s in your veins,” then there is nowhere else to go to learn to sail other than the Annapolis Sailing School! The three day Basic Keelboat Certification course (101) was pure joy and loads of fun. Chris and Emily are the best instructors on earth. They provide an amazing wealth of knowledge to help you gain confidence at the helm. From day one you feel like part of the family, I highly recommend this experience. It will blow your mind and change your life. It sure did for me!!!!!
Written July 1, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Shawna M
2 contributions
5.0 of 5 bubbles
Jun 2020 • Couples
After playing boat pinball when trying to dock, I booked a power boat lesson for my husband and I with John. As new boaters, we learned more in 3 hours than we could have learned after years of boating. Took my girlfriends out tonight and docked the boat in a tight spot like a BOSS! I highly recommend this place.
Written June 24, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

627Tai
Philadelphia, PA24 contributions
5.0 of 5 bubbles
Oct 2021
We have taken two courses with Annapolis Sailing School and enjoyed both. Their instructors are knowledgeable, fun and thorough. The sailboats are very safe and sailing in Annapolis Harbor is beautiful, albeit busy as anything with all the boat traffic.
Written October 21, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Nate C
2 contributions
5.0 of 5 bubbles
May 2024 • Friends
Yesterday, I finished taking the 5-day ASA 101 sailing and beyond basic course at Annapolis Sailing School. Across the DMV, the Annapolis Sailing School has a strongly positive reputation, so I went into it with high hopes and large expectations. After five days, I can say unequivocally that Annapolis Sailing School ("AS") surpassed everything I was expecting. The instructors were friendly and knowledgeable, and the facilities are kept in great shape.

For the first three days, the instructors were Andy, Jonah, Steve, and Carrie, with Andy being my main instructor. He was fantastic! Funny, gregarious, and clearly experienced. On the last two days, Jonah was the only instructor (the class size was only four for the final two days), and he did a phenomenal job in teaching us some of the more advanced techniques. It's so rare to find instructors who not only are very knowledgeable, but are also enthusiastic about teaching. I went into this with some sailing experience, which did help, but I also saw people with no sailing experience go from entering a sailboat with some trepidation to practically jumping into it on the last day. If you take this course, you will learn how to sail.

Going forward, I plan to take ASA 103, 104, and 105 at AS as well. I'm really looking forward to learning more!
Written May 11, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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Annapolis Sailing School - All You Need to Know BEFORE You Go (2024)

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