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
  • J K. Avatar
    J K.
    7/30/2020 - Google

    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.

    Steve W. Avatar
    Steve W.
    7/21/2020 - Google

    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.

    John P. Avatar
    John P.
    7/24/2020 - Google

    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.

  • Alan G. Avatar
    Alan G.
    6/24/2020 - Google

    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!👍 👍

    Jeffrey P. Avatar
    Jeffrey P.
    8/21/2020 - Google

    Annapolis Sailing School is one of the few places in the area that offers small sailboats for day rentals. They have Rainbow 24 sailboats which are a very safe and stable boat. As an experienced sailor that had never rented from them before, I had to do short 30 minute checkout sail with an instructor to demonstrate I was a competent skipper. I sailed with my two adult children and we had a very good experience. It was a day with light winds. When the wind died, the sailing school staff gave us a tow back to the dock since the boats do not have motors. The Annapolis Harbor area where we sailed is a pleasant and scenic area. So if you are looking to rent a sailboat for day sailing in the Central Maryland area I would recommend Annapolis Sailing School. The staff is excellent, particularly Brenda in the office and our instructor Ryan. They also offer classes there if you want to learn to sail or improve your skills.

    Negash A. Avatar
    Negash A.
    8/22/2020 - Google

    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.

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