Seriously Fun

Learn to sail the Annapolis Way

Book Courses
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Adult Sailing LessonsWe Can Teach You

Teach Me ASA Certification
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Youth Sailing LessonsWe Can Teach Your Children

Teach My Child
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Join Keelboat ClubBe a Social Sailor

Let's Connect
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Rent a SailboatYou Can Borrow Ours

Hand Me The Lines
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Evening Sailboat ChartersWe are the Perfect Host

The Sunset Awaits
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Powerboat SpecialFeel the Need for Speed

Let's Motor

Which Course is Right For Me?

That's Me

I want to be able to operate a vessel I already own or intend to buy.

That's Me

I intend on renting or chartering sailboats in the future.

That's Me

I want to explore the art of sailing and am looking for a great experience.

That's Me

I'm looking to learn at my own pace with personalized private instruction.

Annapolis Sailing Experience

Sailing is an Experience to be Enjoyed Over a Lifetime

We provide a community at the Annapolis Sailing School for your ongoing growth and enjoyment. We offer day boat rentals, Keelboat Club, KidShip Sailing, Annapolis Powerboat School, Annapolis Water Experiences with stand-up paddle boarding, and events at our beautiful location on Bembe Beach.

About Us Our Courses
  • 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. There's 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.

    Casey B.
    10/22/2020

    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. You'll put your self in a happy place.

    John P.
    7/24/2020

    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 they're 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.

    Jeff M.
    9/27/2020
  • 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.

    J K.
    7/30/2020

    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.

    Steve W.
    7/21/2020

    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.

    David P.
    10/08/2020
  • 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.

    Negash A.
    8/22/2020

    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!

    Kirk S.
    10/17/2020

    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!👍 👍

    Alan G.
    6/24/2020

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