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Address: 7001 Bembe Beach Rd, Annapolis, MD 21403-3615
Phone Number:
+1 410-267-7205
09:00 - 17:00
Open now
See all hours
Sun - Sat 09:00 - 17:00

Annapolis Sailing School is a family owned water sports experience. We can...

Annapolis Sailing School is a family owned water sports experience. We can teach anyone! From introductions to sailing, to getting your certifications, we have something for everyone.

Our newest offers include our Evening Sail, which is a two hour tour of the Annapolis area on our brand new 37 ft Beneteau's. No Learning Necessary. BYOB. It's all about the fun!

If you're visiting from out of town and looking for a way to spend time on the water, Call us and ask about our TrySail lessons. It's a great way to get groups of 2 to 4 sailing comfortably for a few hours at a very approachable price.

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TripAdvisor Reviewer Highlights

Read all 35 reviews
Visitor rating
  • 31
  • 2
    Very good
  • 0
  • 1
  • 1
Outstanding Sailing Education

I just finished my ASA101, ASA103, and ASA104 certifications with this outfit and highly recommend Annapolis Sailing School. I looked at several different places and decided to... read more

Reviewed 2 days ago
Adam J
Washington DC, District of Columbia
via mobile
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35 Reviews from our TripAdvisor Community

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Showing 35: English reviews
Washington DC, District of Columbia
Level Contributor
20 reviews
common_n_attraction_reviews_1bd8 7 helpful votes
Reviewed 2 days ago NEW via mobile

I just finished my ASA101, ASA103, and ASA104 certifications with this outfit and highly recommend Annapolis Sailing School. I looked at several different places and decided to go with this one due to the types of boats, location, and very limited class sizes. If memory serves, it wasn't the cheapest option out there - but the bang for the buck... More 

Thank Adam J
1 review
Reviewed 1 week ago via mobile

Amazing week long ASA course. Wonderful instructors. Took the time to answer questions as well as needed skills for safe, fun filled sailing experience.

Thank Megan V
Washington DC, District of Columbia
Level Contributor
18 reviews
8 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
Reviewed 1 week ago

A friend and I did the intro "2 Hour Try Sail." It was fantastic. Our instructor was really informative and helped us get a good sense of working the sails/tiller. I'm definitely going to continue on with the ASA Certifications and plan on joining the Keelboat Club to rent all summer long.

1 Thank BenInDC
Washington, DC
Level Contributor
86 reviews
20 attraction reviews
common_n_attraction_reviews_1bd8 38 helpful votes
Reviewed 2 weeks ago

Your can either go on a twilight cruise, or, if you really want to learn sailing there are courses available. I took Basic Keelboat and Basic Coastal Cruising. Instructors were fantastic and the boats you use are ideal. Can't go wrong if you want ASA certifications.

Thank musicman1961
1 review
Reviewed 3 weeks ago

completing a basic sailing course. Several hours of fun sailing the a nice boat with nice friendly people. Learned a lot of important information at the same time.

Thank Юрий В
Odenton, Maryland
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 17 September 2016

We purchased a groupon for a two hour sailing lesson with up to five people. The others didn't show up so we wound up getting a private tour! Mike was our guide, and really let us "take the reins." He offered as much info as we wanted, but also allowed us to just relax and enjoy the beautiful weather. The... More 

Thank jorons89
JC0613, Manager at Annapolis Sailing School, responded to this review

Thanks for your kind words More 

Level Contributor
4 reviews
Reviewed 10 September 2016 via mobile

John did a fantastic job of helping us feel more comfortable on our new boat. We had a wonderful day, had a great time and learned enough to make our heads explode. It was worth every penny. Looking forward to another session after we compile our list of questions. Highly recommend !

Thank sarahb2345
1 review
Reviewed 29 August 2016

Nathan did a wonderful job in my introduction to sailing lesson. Despite being a college student he was very knowledge about sailing. My initial goal is to sail from Annapolis to St. Michaels. Nathan explained that this is doable after approximately seven days of future lessons. When my schedule permits I am interested in taking additional lessons. I recommend the... More 

Thank John P
Fairfax County, Virginia
Level Contributor
42 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 25 helpful votes
Reviewed 22 August 2016

Purchased a Groupon for a two hour "Try Sail." Our instructor, Ben, was personable, and gave us a good overview of sailing. The Rainbow 24s are easy boats to handle and it's a great way to get a different view of Annapolis. Relax and enjoy it. You're not going to become a qualified sailor in a couple of hours, but... More 

1 Thank tikibar
Jacksonville, North Carolina
Level Contributor
87 reviews
39 attraction reviews
common_n_attraction_reviews_1bd8 55 helpful votes
Reviewed 16 July 2016

A tad disorganized. A bunch of hungover college kids working for the place. Some of the "pros" are cranky old cranks they bring in at the last minute. Totally unenjoyable.

1 Thank calinjaxnc

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Questions & Answers

Questions? Get answers from Annapolis Sailing School staff and past visitors.
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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?