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Address: 7001 Bembe Beach Rd, Annapolis, MD 21403-3615
Phone Number: +1 800-638-9192
9:00 am - 5:00 pm
Closed now
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Sun - Sat 9:00 am - 5:00 pm

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 28 reviews
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  • 24
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    Very good
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  • 1
Introduction to Sailing Lesson

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... read more

5 of 5 starsReviewed 4 days ago
John P
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28 Reviews from our TripAdvisor Community

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Showing 28: English reviews
1 review
5 of 5 stars Reviewed 4 days ago NEW

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
Washington DC, District of Columbia
Level Contributor
29 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 21 helpful votes
4 of 5 stars Reviewed 1 week ago

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
84 reviews
34 attraction reviews
common_n_attraction_reviews_1bd8 51 helpful votes
1 of 5 stars Reviewed July 16, 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.

Thank calinjaxnc
New Hope, Pennsylvania
Level Contributor
14 reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed June 26, 2016

I took the Advance Beginner sailing course in April 2016 on their Beneteau 37.. The boat is only one season old, in great condition and fully outfitted. Wow! I was fortunate to be the only student this particular weekend so it was all one-on-one instruction with Captain Pat A. This is a two day course, so there was plenty of... More 

1 Thank CorpEscapee
Level Contributor
191 reviews
48 attraction reviews
common_n_attraction_reviews_1bd8 44 helpful votes
5 of 5 stars Reviewed June 3, 2016 via mobile

My husband had purchased a voucher for a 2 hour sailing lesson for two. The staff was very friendly and helpful with arranging our lesson. Groups can be as large as 6 but we were fortunate to have the instructor to ourselves. The day we sailed was overcast and unfortunately not very windy. Our instructor Matt was friendly and knowledgeable.... More 

1 Thank DMMcGW
1 review
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed May 10, 2016

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... More 

2 Thank Jamey D
Tuscaloosa, Alabama
Level Contributor
4 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed September 28, 2015 via mobile

Great experience - plenty of learning, laughter and fun! Thanks to Captain Pat for a fantastic weekend!

Thank BPW1989
Washington DC, District of Columbia
Level Contributor
91 reviews
32 attraction reviews
common_n_attraction_reviews_1bd8 58 helpful votes
5 of 5 stars Reviewed September 7, 2015 via mobile

I took Course 103: Three-day New Sailor’s Mini Holiday in August 2015. I found the third day really sealed the deal - things started to click. I hadn't been sailing in over 10 years, but it is a true beginners course, so no experience necessary. My two instructors were very knowledgable, experienced and nice. I was at ease right away.... More 

1 Thank MHATW
Alexandria, Virginia
Level Contributor
114 reviews
41 attraction reviews
common_n_attraction_reviews_1bd8 33 helpful votes
5 of 5 stars Reviewed August 13, 2015

I've grown up around sailing, but I've never really learned for myself. I took the Annapolis Sailing School's "Learn to Sail in a Weekend" course and learned so much. I met great people, and learned really practical stuff. I just wish I could have taken more time to practice. You should be prepared for all weather. We were in the... More 

Thank MelBellSkiGirl
Chagrin Falls, Ohio
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed August 11, 2015

My husband and I spent two days and one overnight on a 37' Beneteau sailboat while taking the Intro to Cruising course. We had a very informative instructor and learned so much. This was a great experience and a great first step for us as we decide whether living on a sailboat will be part of our future.

1 Thank JenDaus

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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?