Stop thinking about it and just do it. Def a top flight sailing school in the Mid-Atlantic! I did the combined 101/103 course that allows you to take out a cruiser. The 101 course is great for newbies; the instructors are all highly experienced yet very patient with beginners, you'll have a great time for sure! Since I love cooking, I'm going to use the Scoville scale to compare 101 and 103. If 101 is just a mild bell pepper, then 103 is a jalapeño. Don't take it unless you're ready for a true sailing boot camp! It will kick your ass, especially if you've just come from 101, but you're going to learn A LOT that you can then take with you to digest and practice. You're going to be overloaded with a LOT of information, but just take some time at the end of each day to decompress and process what you've learned and you'll do fine. They are all very passionate about the art of sailing and push you hard to be the best sailor you can be. Def a great experience!!! read more

See all

I wanted to update my review of Annapolis Sailing School. There is one reason: my review last year didn't include Ian Morrison, the new Keelboat club director. It's been a terrific season at ASS. The winds have been so steady into August and the special events (blue angels, dinghy day, Monday night races) have all contributed to creating a real community there. Ian has helped take the club membership up a notch or two. As the club director he takes charge and delivers help and services for the club members and connects members together. "it's your clubhouse" he's said to me more than once. I've learned so much from him this year about rigging and racing. How I love Annapolis Sailing School. Thank you Rick Nelson for bringing Ian on board for us. read more

See all

We had a great time here. Just starting out for ASA 101. Not the most inexpensive school in the area - but lots of plusses. Boats were well maintained, parking and directions were easy, they kept to schedule but still held flexibility for the weather. All staff we met there were friendly and helpful. Instructors were clear and highly experienced and made sure all students understood and practiced the drills. Having the text book prior was pivotal (they shipped it fedex too) - students MUST read it prior if you want to be useful during classes. I really felt all the students were serious about learning skills which was great and so we all worked well together. Would recommend! Actually we hope to go back for ASA 102/103 and higher certifications as we develop. read more

I was a member for two years and enjoyed Monday Night Races. There were occasional spats with nasty crew members, but on the whole, members were friendly and post-race gatherings were fun. But this year, well after I was fully certified to sail a boat and had participated successfully in many races, I was told by the manager and the coach that I had "sailed with an instructor [who] reported that [I] had trouble following instructions and refused to move forward so [I] could utilize the full tiller range to control the boat." I was also accused by the "instructor" of having had a "near collision" that I in fact avoided successfully. The manager and the coach decided that the "correct action" to take was "to limit [my] participation in the [Monday Night Races] to crew member only - no skippering." Basically, the manager and the coach were telling me that I couldn't sail a boat, because manning the tiller ("skippering") is what sailing is all about. I considered this action on their part to be a breach of my contract with the Club. So I quit and had my full membership for the year refunded to me. I had no idea at the time that I was sailing with an "instructor," whatever that is. I had no idea at the time that the "instructor" was evaluating me. I had no idea that when I was manning the tiller, the "instructor" crew member had the right to "instruct" me on what to do. Usually, the person manning the tiller gives the orders. Where I sat in the boat did not impede my being able to steer the boat. I violated no sailing rule. Collisions and near collisions are frequent in races. I have no idea what I was being punished for or why the punishment consisted of depriving me of the right to steer a boat. Annapolis Sailing Association can be fun, but it is poorly managed and some members are overly competitive. Some people in it take racing too seriously, even though members are supposed to "have fun." read more

I haven't been sailing in a while and decided to take ASA 101. The instructors were patient and offered great suggestions. They are very passionate about sailing and genuinely want you to learn as well as have a great time. The location is at the mouth of Back Creek with easy access to the Chesapeake. It is a beautiful spot. I am planning on renting boats from them to practice and take the ASA 103 course. If you want to learn to sail, this is your place. read more

I had a fabulous 3-day (weekday) experience learning how to sail (101 course).-- Instructors were terrific and the balance of subjects taught, time in class and time on the water were all good. Apart from all that -- it was so much fun (the perfect sailing conditions helped!) I highly recommend this course for anyone wanting to learn the basics of sailing. Lots of information and knowledge were imparted. I need to put it all into practice! read more

My wife and I took the Accelerated ASA 101 course here, as well as an evening sail, and we were truly impressed the quality and range of instruction. With a class of 9 students and 3 instructors, we got to experience a variety of perspectives and instruction to make us well-rounded sailors. We feel like we could experience a gamut of situations on the Rainbows, or any other keelboat, and have a great time getting ourselves into or out of any situation we need. The subtle control needed to leave from and return to the dock under sail power alone is a skill I plan to use even on larger boats. I'd like to specifically call out all our excellent instructors, Capt John, Dan, KK, and Dave. They were all top-notch, and I'd love to take another course with any of them again if our schedule allowed. read more

I signed up for the ASA 101 three day course. Staff was responsive and understanding when I had to reschedule at the last minute due to a death in the family. ASA 101 course is appropriate for beginner/inexperienced sailors. Instructors were friendly, experienced and professional. Staff made every effort to maximize time on the water. I'm told that the Rainbow sailboats used for the course were designed specifically for the Annapolis Sailing School. The boats are perfect for training new sailors. The Rainbows are stable and easy to rig. They're forgiving of mistakes so not the most nimble of boats, but can certainly provide a taste of sailing excitement. Kudos to instructors Carrie and Chris for their excellent, safety-conscious instructions. I plan to take further courses with Annapolis Sailing School and would highly recommend. read more

I had a fantastic experience learning to sail with instructors Phil, Natalie, and Scott. They are all knowledgeable, patient, and engaging instructors. The 101 courses was hands on from day one. By the end of the 3 days my fellow classmates and I were all confident and able to sail unaccompanied by instructors. I would highly recommend Annapolis Sailing School! read more

Had a great time renting a boat from Annapolis Sailing School yesterday. The Rainbow 24 is a fun little keelboat (24'). Just big enough to give a stable comfortable ride and small enough to be easily manageable by one sailor and a novice. The staff here went out of their way to set us up at the last minute and the process was painless - I really appreciate the Aloha far from home. The Chesapeake is pretty typical bay sailing, lots of other boats but no swells and the waves were pretty tame. It's ideal if you like to be out on the water but tend to get a little motion sick in rougher seas. There's a video of how to rig the boat online, published by the sailing school - simple and straightforward but watching it will make getting out on the water faster. Would recommend adding a link to the video from the webpage. read more

I took Annapolis Sailing School up on their new "Evening Sail" option this past weekend, and boy was it a blast! We got a couple of friends together and loaded up a cooler full of drinks (BYOB) and dinner food, and set sail under the twilight sun. The cruise lasted roughly 3 hours and our captain took time to teach us little nuisances of both the Bay and the boat (Beneteau 37) we were sailing on... I highly highly recommend this excursion and will be back to take advantage of this, and the other options offered at Annapolis Sailing School in the very near future! Thanks again Captain John!! read more

Annapolis Sailing School - Getting a little lesson at the helm from our awesome captain - Boating Near Me - Annapolis, Maryland

Hilary Ranney-Howes really is the best instructor you can ask for. Fair winds and following seas!

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!!!!! read more

Bought this outing through Groupon. Great 2 hour beginners sailing course. Thomas is a great instructor! Everyone associated with the sailing school was kind and professional. Loved it so much we signed up for the 3 day certified sailing course... read more

Had a great time doing the Basic sailor two day course (Modules A & B). This is a very well run operation with knowledgeable staff, lots of oversight and safety so you will be in good hands. Good location is easy to get to and plenty of parking. Being on the water responsible for the safety of a vessel is a big thing to take on, especially when that vessel requires lots of ropes and pulleys and knowledge and luck with the wind and weird sailing lingo all working together just to go in the direction you want to go, but these guys make it seem easy to learn. We will likely be back for further classes and to do certifications in the future. read more

Bravo Zulu. My wife & I recently completed the ASA 101 certification class at the Annapolis Sailing School. Each day, we spent more than 80% of our time on the specially designed Rainbow sailing vessels learning the fundamentals of sailing in the Severn River. Our three instructors (Gary, Phil, & Kaykay), tag-teamed with each boat to spread their knowledge among all the students. We are ready to join the Keelboat Club at the Annapolis Sailing School to hone our new skills & enjoy our newfound sport. read more

I can't say enough good things about this place - but I'll try. Last week I had basically no sailing experience whatsoever, and just completed their 5-day Basic Keelboat Certification class. I had two wonderful instructors: John & Gary. I'm not qualified to judge their sailing skills, but they're both great teachers - which is even more important. They're very knowledgeable about all things saling, and have the patience and temperament necessary to the task of teaching novices. Everyone at the school was incredibly friendly and helpful. The instruction was appropriately paced, blending classroom with hands-on sailing. When I finished the class and got my certification, I joined their "keelboat club" - which will allow me, for a flat fee, to rent a boat (availability guaranteed) on 72-hours notice, anytime I want, for the next year. I got a 10% discount for signing up shortly after completing the class. Pointers: While they have 3-day classes covering the same material, I personally felt I needed every bit of the 5 days to reach a point where I would even consider taking a boat out on my own. Others probably feel differently. The incremental cost of the additional days makes it well worthwhile. Also, I imagine the bay is a zoo on weekends. I took a week of vacation and was glad I did. I also stayed in town (I live in Silver Spring) to avoid the exhausting commute back and forth. Read up in advance to get the most out of the class. The volume of information is pretty overwhelming. If you know the terms and basics going in, you'll be way ahead of the curve, avoid wasting precious time and get the most out of the actual sailing. As a caveat... I was extraordinarily lucky in that: 1) we had absolutely perfect weather all week; and 2) I was the only student in my class (I appreciated the fact that they didn't just cancel it). read more

Annapolis Sailing School - View from the classroom to the boats and boat dock. - Boating Near Me - Annapolis, Maryland

Back in December, long before anyone was thinking about sailing on the Chesapeake, Annapolis Sailing School offered a Groupon for their 2 hour trial sail. We arrived a bit before our trip time, but when the other couple arrived they got us out on the water right away (so there were 4 of us and the instructor in a 26 Rainbow sailboat so room to stretch out). Our instructor was very knowledgeable and explained everything as she was rigging up the Genoa sail. The purpose of the trial sail is really to see if you would be interested in taking a longer weekend course. We did get to do some jibbing and tacking, but the wind on the bay wasn't really cooperating. However, our instructor kept it entertaining and relaxing. It was an absolutely perfect time. I am considering going back for a longer course. read more

I bought a Groupon sailing lesson for two for my husband's birthday and we had a great time. Availability for booking was better than expected. The two hour intro lesson was great. We were able to try out the different "stations" on the boat for how to operate various things and had a really nice time. I would highly recommend and we would consider doing again. read more

I recently completed the ASA 104 sailing course. The instructor Dave was highly experienced , adaptable and an excellent instructor. The boat was a recent model Beneteau in excellent shape. Even the bilges were spotless. read more

Annapolis Sailing School - Boating Near Me - Annapolis, Maryland

See all

My son and I took the Basic Sailor ASA 101 course here last weekend (early August), and we had a GREAT time. The instructors were all clearly experienced, expert, and engaging, and the mix of classroom time and boat time was perfect. We left feeling confident about the basics and about our skills, and we plan to go back and continue certification. I highly recommend this school! read more

Stayed in the house boat across the water and on a whim we called and asked for someone there to take our picture. They so kindly obliged our request. We are so happy to have the photos as a memory. They were courteous, kind and helpful. The school is in an awesome location with perfect waters to sail! Great views and perfect location. read more

Highly recommend Annapolis Sailing School. A friend and I with little prior sailing wanted a full week immersion to learn the basics and develop confidence for continuing on our own. We selected the Annapolis area based on recommendations about the conditions for learning and then each independently decided that Annapolis Sailing School seemed to be the best fit based upon other reviews and the program offered for our backgrounds and goals. We were not disappointed. During the five day ASA 101 plus "complete sailor" in early April 2016 we enjoyed short, small classes and each morning and afternoon went out in a boat as a pair with an instructor. (I understand their limit is three students per boat.) We had the opportunity to work with a variety of instructors ... all knowledgeable, patient, and good at teaching ... and whose different coaching approaches helped round out our skills. Their fleet of classic Rainbows were great for learning and the equipment was well kept (including new sails for the season). The subject and practical instruction (interspersed in short classes and while on the water) prepared us very well for the ASA 101 certification test as well as the two days of further sailing to build confidence. As others have suggested, for relative newcomers at least, it is well worth completing the reading and going through ASA's online video in advance. We are hooked and will be continuing. read more

We had a nice day but I wish we had done the twilight sailing cruise, looks nicer. Still, cool experience, even without wind. I do not like the smaller boats however - make sure you are getting what you think you are and if you want a bigger boat, ask for it! read more

My husband & I took ASA 101 and ASA 103 through this school. This instructors are excellent - I can't say enough about how willing they are to help you learn at your own level. They are encouraging, patient, positive and respectful. We have also taken other lessons at a University town with a variety of instructors and Annapolis Sailing School tops them! Many thanks to Anna, John and especially Dave. WOW - you'll get more than your money's worth all on behalf of their efforts! Gratitude - Pat & Gordon read more

We had Jeff as our instructor. He was awesome! My boyfriend and I had a great time and learned a lot about sailing. We went out on the sail boat with another couple we didn't know but we quickly became friends. I would definitely come back and sail again! Thanks Jeff! read more

Annapolis Sailing School - We had a great time learning to said with Jeff! - Boating Near Me - Annapolis, Maryland

Had a fantastic time out on an Annapolis sunset sail with some good friends, a little BYOB, and of course, the Cap himself Captain John. Can't say I'm much of a sailor but Captain John was quick to show us the ropes so I could learn a thing or two while still just kicking back and enjoying the views. Highly recommend this sailing school to both grasp an understanding of sailing as well as just enjoy being on some beautiful boats in the bay. read more

Annapolis Sailing School - Kicking back and enjoying the views - Boating Near Me - Annapolis, Maryland

Definitely recommend doing your ASA 101 (and more!) here. Great instructors, perfect location whether you're coming from DC, Baltimore or the surrounding area, it's fun and you get your certification in just one weekend. You get a discount if you get together a group of 6 people! get your friends and family together and learn sailing, it will be 100% worth it read more

My partner and I made reservations for today's 9 AM 2-hour Trysail intro course about 3-4 weeks ago and do not have enough positive things to say. We arrived about 10 minutes early and were immediately introduced to our instructor, Michael, after the quick check-in process. Our entire trip was almost 2 hours and 20 minutes of learning and fun! We were paired up with another couple. Both they and my partner had prior sailing experience, but Michael made sure to cover all the basics and include me in all of the activities. We all had a chance to steer the boat as well as help out with the sails. It was a great way to spend the first half of the day and we do not have enough positive things to say about our instructor. He was knowledgable, friendly and extremely calm (even when I got a bit anxious). Michael is an A+ instructor and anyone would be lucky to take a course with him. read more

There are far cheaper options and better qualified instructors. One of my instructors was also sexist and rude, and I would not feel comfortable returning for any reason. read more

I took the two-day sailing calls with Annapolis Sailing School. Fantastic. Perfect mix of classroom, dockside, and on the water training. Art and John are outstanding instructors. read more

I had great experience taking ASA 101, 103 and 104. Good instructors, lots of sailing time, well structured and organized classes. I'm signing up for 105 next. read more

My fiancee and I attended a 2 hour Trysail intro course on a Saturday afternoon. We had a great time with our instructor Hugo. He was very experienced and spent a lot of time explaining the fundamentals of sailing to our group. Overall, it was an excellent way to spend a few hours on the water while learning the basics of sailing. Highly recommend it. read more

I just took the Accelerated 101 sailing class and it was excellent. I learned a lot in just a few days and the instructors were extremely helpful and patient. Great experience! read more

This is a great place to learn to sail! Beautiful location, great instructors, and fun sailboats combine for an outstanding experience. I took the ASA 101 accelerated course (3 sessions over the course of 1 weekend) and enjoyed the mix of classroom study and practical sailing exercises. I plan to pursue additional certifications in the future and will do so at the Annapolis Sailing School! read more

I just graduated from the Basic Sailor Certified Accelerated (ASA 101) today. This is the course that starts Friday night (with classroom instruction) and then runs through Saturday and Sunday. Rick was our classroom instructor on Friday night. He did a really great job of moving quickly through the material while making it stick using visual aids. Our instructors on Saturday and Sunday were Gary, John, and Graham. All had different styles of teaching, but all were patient, knowledgable, and helpful. I feel ready to venture out and look forward to getting more practice soon! read more

Hi this was a great experience today we did this on a Groupon and had a fabulous time. The instructor was very knowledgeable and friendly. Would definitely do this again. read more

Went out on the Sunset Sail a few weeks ago and it was a great time! Captain John made sure we all knew what we were doing and made sure we had fun at the same time. We brought a cooler of drinks and just relaxed while watching the sun go down. A great evening out on the water with great people. Loved the Annapolis Sailing School! read more

Great sailing school. Knowledge and friendly instructors...you can't beat sailing in the Chesapeake!

I took the ASA 101 Basic Sailing Certification course and it was worth every penny. I definitely plan on coming back for more. I had some sailing experience when i was younger, but i wanted to start at the basic level and that was helpful. Special kudos to John, Brett, Natalie, and Nathan - our instructors for the weekend. If you have a desire to sail and you have some experience or none at all - doesn't matter. We were all novices and they walked us through everything. Key afterwards is to get experience and the school has resources that may be helpful in hooking you up with other people who have boats and want crew read more