The Annapolis Sailing School is a wonderful place to learn to sail and get your ASA certifications. Located on a very wide part of bay, you sail right off the docks and start learning! The 🌈 fleet of boats are perfect to learn on and the instructors are fantastic!!

This is one of the very few reviews I have written. The experience was exemplary. I took the ASA 101 course with no sailing experience and the comprehensive lesson plan steadily guided me up the learning curve at an appropriate pace. What sets this experience apart is the expertise, patience and camaraderie that instructors share with students. I would like to thank John, an owner, for his insight and humor, and Chris, an instructor, for his guidance in all matters of sailing life. I’d particularly like to thank my instructor, Emily, who set the perfect tone, in the boat and out, to form a partnership in learning among her crew of students and encouraging us to achieve significant learning outcomes in a respectful and enjoyable environment - she is simply outstanding. I realized this experience was special and began to feel nostalgic even as I drove away that last day. And, yes, I plan to be back again and again

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.

I cannot emphasize what an incredible experience I had at Annapolis Sailing School. Having just purchased my first sailboat, I registered myself and my Dad for the 5-day ASA certification 101/103 hybrid course. Both of our instructors Dan and Paul were fantastically skilled. As a complete novice, I walked away with a great sense of confidence and skill set. My Dad who grew up sailing/boating on the Severn/Chesapeake Bay was astonished by how much he did not know -even with all of his previous experience- and was able to learn throughout the course. He was so pleased with the course content, patience of the instructors, and class size. If you want to learn how to sail from the best, there is no other place to learn. You must go to Annapolis Sailing School! Thank you for the wonderful experience. Both my Dad and I look forward to continuing our education with the team at Annapolis Sailing School.

Had a wonderful sail with Andrew, one of the school’s instructors. My wife and I were looking for an experience on a larger boat (not lesson-ready yet!). Andrew was fantastic, super relaxed and knowledgeable. We had a great time and even learned a few things. Looking forward to school in the spring!

We spent four days learning the basics of sailing and had a wonderful time. The instructor makes a big difference, the first day we had a young woman who didnt give much instructions and the wind was up and it was tough but the other days we had someone who directed and taught a lot more and it was smoother and more helpful. Would definitely do it again

A fine introduction to sailing. Staff is friendly and authoritative. No question was stupid. All questions answered well. Highly recommend. Worth the money.

I used the beautiful setting of this sailing school’s property to propose to my girlfriend (now fiancée). I contacted this place during last minute planning and we quickly and smoothly worked out a very fair price for me to be able to use the beach to set up a beach fire picnic style engagement night. It was amazing and she of course said yet. It’d be hard to say no standing next to the water at this place with the great views it has. I can’t speak for the sailing school itself, which is their actual line of business, but I can say that the staff that run the sailing school were extremely professional, kind, accommodating, quick to act, and responsive, which made this life event so much easier for me. Thank you

08/23/21 drove from Central Jersey to Annapolis for the 203 instructor qualification course. I will say it was well worth the 197 mile drive each way. The staff are friendly and the facility is amazing, well keep, and has perfect access to the Chesapeake. Capt. instructor John Cosby the Marina Manager met me in the morning he introduced me to my instructor Duncan Hood. As I was speaking with him I couldnt help but think I had met him before. Suddenly, I realized Duncan Hood has starred in the ASA sailing made easy videos starting from 2008.I had studied and practiced maneuvers for days in preparation for this IQC yet, nothing prepared me for what I was about to undergo.First, I was the only IQC 203 student which meant I got personalized instruction.Second, Capt. John Cosby would also instruct me on systems of the vessel (2015 Beneteau 37). Duncan took the lead on the water his instructions were precise and clear. additionally, his quick sense of humor really made me laugh. I felt at ease as if I were sailing with old time friends. Capt. John was outstanding he would follow up with helpful tips.Then it came as I was getting comfortable with the vessel the blind fold test I wont reveal what it is, you must experience it yourself to appreciate how proficient they are at what they do namely, teaching the teachers.Now imagine creating a lesson plan and teaching these pros. yet, the points and critique were invaluable to me. I will incorporate the advise given.lastly, the second half of the day Capt. John Cosby goes into systems problem solving he creates issues inside and outside the vessel that have to be found and resolved before setting sail.As a whole I could not have had a better day, they treated me as a fellow instructor. I laughed, I learned, I sailed a beautiful vessel on the Chesapeake, and was certified by professional instructors.Whats better than this Sailing the Caribbean? LOL

Captain John was fantastic! He was very patient while teaching my wife and daughter how to operate our boat. Great learning experience on our boat.

Great place to rent a Rainbow 24 for an excellent day sailing on the Bay near the Naval Academy. Friendly, helpful staff, boats well kept.

The Annapolis Sailing School staff are professional, helpful, and kind. It has been a pleasure to learn to sail at this school.

👍The people that work here are very professional and my visit was great i highly recommend this place... check them out.

Amazing location to learn to sail!

What an amazing time with the Annapolis Sailing School this season. Since my I completed my initial training they have really gone the extra distance to tailor a program for my needs and skill level. I are member of the Keel Boat Club at the premiere level such that I can sail their 30 Catalina. Sailing a boat like the 30 Catalina has been a bucket list item of mine for years and with the help and support of the school, I have been able to achieve this in under a year and a half....confidently, with safety and success in mind. Now I can take my family and guests all over the bay with the school watching over us.Key to this success has been the school manager John Cosby. After my initial 103 training he spent several additional weekend sessions with me on the Catalina to help me gain my confidence before me taking my family out on the boat. His insight to sailing and pleasant disposiiton is perfect for instruction and helps make learning some of the tasks that I found difficult much easier. This was the kind of help that I needed, especially after my surgery last summer that kept me off my feet for six weeks. In fact, John even came to the hospital to visit me, brining me the next course book for cruising. Wow, what a boost to my recovery!I am already looking forward to next season and the free seminars that John offers over the winter. And my next certification course.If you have ever wanted to learn to sail, stop by and see him. Visit with some of the other staff, they are awesome too. Look around the docks and the grounds, its beautiful there. You will find that all together the place is an Annapolis gem!

I just wrapped up the basic intro to sailing class and had an awesome experience with Annapolis Sailing School. Instructors Art and John were patient, knowledgeable, helpful, and fun to learn from. I was feeling overwhelmed with the amount of study material before coming to the class, but their practical explanations, low-pressure approach, and genuine love of sailing made the course engaging and nowhere near as intimidating as I expected. Theres really no substitute for getting on the boat with experienced and enthusiastic sailors who help simplify the essentials. I got the sense that the entire staff is passionate about introducing students to sailing and make you feel welcomed.

My girlfriend and I had the most amazing time at the Annapolis Sailing School! We spent a weekend in Annapolis and the staff was extremely helpful and went so far as to suggest great accommodations while we stayed in the area. On a friend’s suggestion we did the Evening Sail after getting in midday to the city and it was truly one of the most fun and informative lessons. We even got to bring a bottle of wine and just enjoy the sunset at the end of the night while our instructor, John, got us safely back to port!The second day we did Trysail package, which I would also highly recommend. We were situated with another couple and everyone took turns at the tiller while learning the basics on a bright and sunny day (sunscreen and sunglasses are a must!).I have to admit that sailing has always been more of my girlfriends hobby but I truly had a fantastic weekend. Now with the new Power Boat School, I am that much more excited for our next water adventure in Annapolis 😊

Annapolis Sailing School is one of the few places in the area that offers small sailboats for day rentals. They have Rainbow 24 sailboats which are a very safe and stable boat. As an experienced sailor that had never rented from them before, I had to do short 30 minute checkout sail with an instructor to demonstrate I was a competent skipper. I sailed with my two adult children and we had a very good experience. It was a day with light winds. When the wind died, the sailing school staff gave us a tow back to the dock since the boats do not have motors. The Annapolis Harbor area where we sailed is a pleasant and scenic area. So if you are looking to rent a sailboat for day sailing in the Central Maryland area I would recommend Annapolis Sailing School. The staff is excellent, particularly Brenda in the office and our instructor Ryan. They also offer classes there if you want to learn to sail or improve your skills.

Fantastic experience getting my ASA101 Keelboat certification. Owner John, and Art and all the instructors were skilled, patient and communicated with best sailor dispositions!, making learning and sailing real fun for everyone. If there was ever need, they got dinghys out to tow you back in minutes! I HIGHLY recommend the Annapolis Sailing School.

The 2 day beginner class was a perfect blend of classroom and hands-on training. It was a perfect way to spend a weekend with my 2 teenager daughters. We all feel like we have a solid foundation in sailing. Dan the Man was our instructor and he was awesome -- patient, knowledgeable and full of corny dad jokes. I highly recommend this school.

Great place to learn to sail. Instructors were great, the course was well thought through and the sailing was loads of fun. We did the 3 day weekend class and absolutely loved it. Highly recommended for anyone wanting to learn to sail.

All round top quality and professional outfit. Everyone is so friendly and the whole experience is fun from start to finish. Brenda is amazing and our instructor Tommy was the epitome of the calmness, patience and knowledge. You knew you were in safe and experienced hands. Two giant thumbs up!👍 👍

Just completed my ASA 103 course this week with Andrew as our instructor. Loved the course and Andrew was a great instructor - I thoroughly enjoyed this sailing + learning experience and am awaiting for the next ASA 104 courses to be offered! Easy school with good people - down to earth and no sailing snobbery often experienced with larger marinas.

I never sailed a day in my life, so I had no idea what to expect, but the staff was really friendly and supportive, and they clearly enjoy what theyre doing. After finishing the intro to sailing class, I took out a few friends and family, and the dock hands helped with the areas I struggled with during class. This was a great starting point, and I highly recommend you get into club if you like the class.

Fantastic experience. The sailing was hands on with great instruction. Will definitely take some more sailing classes with them. I highly recommended this sailing school

Awesome Sailing School! Thoroughly enjoyed the ASA 101 Complete Sailor program. I cant wait for next season to work on advanced skills and certifications!

My son and I took ASA-101 Basic Keelboat certification class before he headed out to start his freshman year in college. It was an awesome and memorable experience. The instructors are superb and patient delivering the lesson at a pace that kept everyone engaged. I highly recommend the Annapolis Sailing school.

What more could I say about Annapolis Sailing School? They have made my COVID summer of 2020 as fun as possible. Very courteous, eager to help, flexible and accommodating.I especially want to call out KK, Brenda, John, Natalie and Ryan who all make the sailing experience easy and fun.If you need a very fun getaway, go and rent a 24 Rainbow for a few hours and then sit on the beach in the shade and have a much-earned beer. Youll put your self in a happy place.

The instructors were very knowledgeable and patient with the students. I learned a lot from the course

They have a great staff of instructors and we spent most of our time on the water learning by experience.

We rented a 21’ Rainbow for a day of sailing and had a great experience! Friendly, knowledgeable staff and the equipment was well maintained.

Outstanding staff and program. Im sure it has to be one of the very best sailing schools in the country.

Love this place. They do a great job at teaching and are very accommodating.

I cannot say enough good things about this place. Captain John is fantastic. There is a really nice down-to-earth, family-friendly atmosphere. I will definitely be returning.

The staff is so helpful and knowledgeable to help make learning to sail easy and fun!

Took the ASA 103 class with instructor Paul on the 37-foot Beneteau and learned a ton. Took my first class at the school in 1989 and just love this place.

My wife & I enrolled in the ASA 101 Basic Sailing course last summer. During the three day course, we learned the basics of safely sailing the 24 Rainbow sailboats that are owned by the Annapolis Sailing School. We then joined the Keelboat Club. As club members, we typically take a Rainbow out for a 1/2 day each week to hone our sailing skills. The Monday night sailboat races with other Keelboat Club members add the excitement of some friendly competition & post race socialization. The occasional harbor cruises and a fall weekend excursion to Rock Hall provided additional opportunities to socialize with fellow sailors. Finally, the staff at the Annapolis Sailing School is particularly friendly and helpful. If the wind dies down and you need a tow, a quick phone call to the office results in a rescue skiff in minutes.

Love this place, their facility and the people that run it!

Just finished Complete Sailor 5 day course. Started with zero sailing experience and felt comfortable with the foundational concepts and practical sailing at the end. First rate teachers. Highly recommend.

If you are thinking about it, choose ASA. It was an incredible experience. In 2.5 days I learned so much. Saturday am was my first time on a sailboat and by Sunday afternoon I was certified. The staff gives so much and teaches so well. Sailing there was so approachable and they get you on the water quickly and confidently.

We had a wonderful experience at the Annapolis Sailing School and will absolutely be coming back. I joined a group of friends for an evening sail and it was gorgeous. Our captain, John, was so knowledgeable and professional and put everyone at ease as we sailed the bay. I couldnt imagine a more perfect location to sail from, well definitely be back!

Such a fantastic experience. We hadnt rented a boat here before and would love to come back again!

Excellent staff. Wonderful experience. Ill be back for more.

Just finished Course 102, and it was great! All of the instructors were knowledgeable and patient with the new sailors, classroom time was kept to a minimum, we were out on the boat a majority of the time. I highly recommend Annapolis Sailing School.

I found the staff friendly and knowledgeable and quite accommodating; very good place to start or refresh your sailing skills. Certainly a school to pursue sailing certification at. They even have their own small beach and tent on the grounds! I also note that they were very family-friendly and successfully took my two girls aged 12 and 16 sailing with no hitches

You are in great hands at ASS. I took the 5 day 101 Keelboat course and came out with the ability to single hand one around the bay (although I havent yet). Every staff member at ASS will go out of their way to help you. Art, Sherri and Nathan all instructed me at different points of the week, but I spent the most time with Sherri with whom I made pretty good friends. The staff are passionate about sailing, so they genuinely want to help you. I would highly recommend the 101 course and will be taking more courses in the future.

I had a great experience recently with a trysail course. Art was a terrific teacher and we had a blast on the water. Learned a lot as well. Id recommend if you are curious about sailing.

Love the place and go there frequently!!!

My granddaughter is taking her first sailing class (6yrs) and is excited to get there every day. Great in class room activities, and on the water experiences to fill her with memories. Cant wait for her to start giving me commands during our sailing trips.

This was one of the most amazing experiences that we had as a family. Fantastic day, perfect weather, good wind, and an excellent Captain.Our Captain was perfect, very knowledgable about the area (which you would expect!), but was also very engaging with our family. We learned a lot (and it was FUN), experienced a lot, and it was enjoyable for all.We will definitely come back, and in fact, we are signing up for lessons as a birthday present for one of the family members. I highly recommend the school, the staff, and the facility!

Such a friendly place! My husband and I did the 2 hour introduction to sailing class and our guide was informative and helped us learn a lot in a friendly environment!

Extremely disappointed in management! My husband is a professional sailor and has been intending to introduce our kids to sailing. We came to Annapolis Sailing School from Virginia to look at the place and inquire if we could in future (possibly the following week-end) rent a boat with the family and what the rules would be for that. Because our kids are little and the offer was to get a boat for 4 hours we inquired if they had other offers for a 2 hour ride because 4 hours would be too much for the kids out on a boat (the kids are 2 and 6 years old). The unpleasant man who presented himself as a managing director of that place told us in a pretty rude way that we can go for what ever time we needed but he wasnt going to drop the prices for us. We thought his answer was tense but maintained a positive attitude and told him we would walk around and think about it. We set at the pier and then on the shore for about 30 minutes talking and planning when we could come out there maybe with just the older kid and rent the boat for 4 hours. 30 minutes later kids got hungry and we got up to leave when the managing director approached us and told us to get out because we were not renting anything and it was a private property! He was basically screaming and spitting at us pointing at the private property sign! We left immediately and as we got in the car the kids started crying asking why that gentleman yelled at us and if they did something wrong! I mean seriously! this is how bad this was! I mean its not like we came and had a picnic there. We literary just set and talked and left! His name was John and the last name I believe was Cosby (or something like that). This guy really needs to go improve his soft skills. Needless to say we will not rent from this place or become club members. In addition we will make every effort to notify others (and we do have a lot of friends in VA who wanted to check that place out and will not do so based on our review). I mean imagine going to a store and wander around thinking what and when you are going to buy there and then being kicked out for wandering around for too long and not buying anything!!! Who would want to come back!? Ever!?

Attended the Sailing 101 class and it was fantastic. Well organized, thoughtful and passionate instruction, and it all made for a great experience.

We had a great experience with the Annapolis Sailing team: easy registration, check-in, great boats for all skill levels, and, above all, very solid staff and coaches. The venue itself is ideal for sailing - quick and easy access to top sailing and beautiful views of the surrounding area.

Really learning to sail is a bucket list item for me and I highly recommend Annapolis Sailing School. Great instructors, an ideal location, and their keelboat club is a hidden bonus. Two years ago I took a week long course with them which has been a great foundation. Since then Ive taken advantage of their keelboat club to get lots of time on the water affordably, particularly with their Monday night racing which is social and very accessible for newcomers as well as sailors with some skill. This year they added a performance sailing class and opportunities to sail on the schools Farr 230 in Annapolis Yacht Clubs Wednesday night race series. With students at the helm and trimming the sheets--and patient, talented instructors completing the crew--this has been an incredibly fun experience, on a boat fast enough to keep us in the middle of the competition, and when I think about the extra coaching time an absolute steal.

I found the instructor rude and sexist--he kept cornering me to harass. After I asked the instructor to lay off, I was singled out along with my partner as the only team to test in the rain. The guys enjoyed the sun in the early part of the day and took the written in the afternoon. We were kept inside for the written test during the morning even though there were clearly enough boats. I had hoped to find a place to make lifelong memories--I envisioned sailing each summer and getting to know the community. Instead I faced mild hazing and a total lack of professionalism. Now I regret having paid so much for a negative experience, and I will never return to rent.

Killer location, good people, fun times.

I recommend to everyone.Staff are great and great. Beautiful location and amazing experience.

Very good instructors, great value, learned a lot quickly. Minimum of classroom time and lots of practical experience.

The instructors are very nice people and the try sail lesson was just awesome!Thank you.

The instructors were great! The overall experience was amazing!

THE Place to learn to sail.

Sam is the best!!! My father and I got our 101, 103 and 104 last Fall!