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Address: 7001 Bembe Beach Rd, Annapolis, MD 21403-3615
Phone Number:
+1 410-267-7205
09:00 - 17:00
Closed 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 30 reviews
Visitor rating
  • 26
  • 2
    Very good
  • 0
  • 1
  • 1
Great Sailing Lesson with Mike

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... read more

5 of 5 bubblesReviewed 18 September 2016
Odenton, Maryland
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30 Reviews from our TripAdvisor Community

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Showing 30: English reviews
Odenton, Maryland
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 18 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
5 of 5 bubbles 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
5 of 5 bubbles 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 24 helpful votes
4 of 5 bubbles 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 54 helpful votes
1 of 5 bubbles 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
New Hope, Pennsylvania
Level Contributor
14 reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed 26 June 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
207 reviews
50 attraction reviews
common_n_attraction_reviews_1bd8 49 helpful votes
5 of 5 bubbles Reviewed 4 June 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 

2 Thank DMMcGW
1 review
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed 11 May 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 bubbles Reviewed 29 September 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
100 reviews
33 attraction reviews
common_n_attraction_reviews_1bd8 75 helpful votes
5 of 5 bubbles Reviewed 7 September 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

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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?