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Beginner Classes

Sail with confidence!
Recognized as ASA’s School of the Year

If you've never stepped on a boat before, or just getting started learning to sail you're in the right place.

In all our beginner classes you'll learn step-by-step instructions for everything from hoisting the sail to docking. All of our courses are summarized below so take a cruise through our course calendar to check availability and dates, enroll in your next class!

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  • ASA 105 COASTAL NAVIGATION | JANUARY 2027 | MADISON, WI: $597.00

    Navigate with confidence, even when you cannot rely solely on electronic navigation. ASA 105 Coastal Navigation is an in-depth, classroom-based course that teaches you how to interpret nautical charts, plot courses and positions, use maritime publications and account for tides, currents, wind and leeway when planning a passage.

    Through instructor-led lessons and hands-on chart work, you’ll develop practical navigation skills that strengthen your understanding of how your vessel interacts with the world around it. No previous ASA certification is required, and the course is especially valuable for sailors preparing for ASA 106 Advanced Coastal Cruising.

    Format: 25.5 hours of live, in-person instruction in Madison, Wisconsin, on January 18, 19, 21, 22 and 23, 2027.

    Click the REGISTER button to view the complete schedule, see everything included with tuition and reserve your place.

  • ASA 101 Keelboat 1 | May 29th & May 30th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to become a sailor? ASA 101 Keelboat Sailing 1 is the perfect place to begin. No previous sailing experience is required.

     

    Over one hands-on weekend, you’ll learn the fundamentals of sailing aboard a tiller-steered Hunter 216. With no more than four students per class, everyone receives plenty of time at the helm, trimming sails, practicing maneuvers, and rotating through the different crew positions.

     

    You’ll build a strong foundation in boat handling, sail trim, safety, sailing terminology, crew-overboard recovery, knots, and more, all while gaining the skills and confidence to continue your sailing journey.

     

    Your course includes two full days of hands-on sailing instruction aboard one of our training sailboats, use of all sailing equipment, the official ASA textbook and course materials, plus the ASA 101 examination and certification.

     

    Click the REGISTER button below to view the complete course details, available dates, and tuition, or reserve your place in an upcoming class.

  • ASA 101 Keelboat 1 | June 19th & June 20th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to become a sailor? ASA 101 Keelboat Sailing 1 is the perfect place to begin. No previous sailing experience is required.

     

    Over one hands-on weekend, you’ll learn the fundamentals of sailing aboard a tiller-steered Hunter 216. With no more than four students per class, everyone receives plenty of time at the helm, trimming sails, practicing maneuvers, and rotating through the different crew positions.

     

    You’ll build a strong foundation in boat handling, sail trim, safety, sailing terminology, crew-overboard recovery, knots, and more, all while gaining the skills and confidence to continue your sailing journey.

     

    Your course includes two full days of hands-on sailing instruction aboard one of our training sailboats, use of all sailing equipment, the official ASA textbook and course materials, plus the ASA 101 examination and certification.

     

    Click the REGISTER button below to view the complete course details, available dates, and tuition, or reserve your place in an upcoming class.

  • ASA 103 Basic Coastal Cruising | June 26th & 27th, 2027 | Port Washington, WI: $897.00

    PORT WASHINGTON, WI
    Prerequisites: ASA 101 Keelboat Sailing 1

    Ready to move beyond the basics? ASA 103 Coastal Cruising builds on the foundation developed in ASA 101 and introduces you to the skills needed to safely operate a larger, auxiliary-powered cruising sailboat.

     

    During this intensive two-day course, you’ll gain hands-on experience with boat handling under sail and power, docking, sail trim, anchoring, navigation, weather, safety procedures, boat systems, and cruise preparation.


    By the end of the course, you’ll have greater confidence handling a cruising sailboat and a solid foundation for planning and enjoying daytime coastal cruises. You’ll also be prepared to continue building your skills with ASA 104: Bareboat Cruising.


    Format: This course is offered as an intensive two-day course.


    Click the REGISTER button to explore the complete course details, available dates, and tuition, or to reserve your place.

  • ASA 111: Sailing 101 Review | July 2nd, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00

    South Shore Yacht Club
    Prerequisites: ASA 101, Keelboat Sailing 1

    Has it been a while since your ASA 101 course? Get back aboard, refresh your sailing skills and rebuild your confidence during this hands-on review designed for sailors who have already earned their ASA 101 certification.

     

    You’ll revisit the fundamentals of keelboat sailing, including sail trim, points of sail, tacking, jibing, crew communication, safety procedures, crew-overboard recovery and essential knots. There are no examinations and no new textbook required. This is simply an opportunity to practice, ask questions and spend focused time sailing with an instructor.

     

    Prerequisite: ASA 101 Keelboat Sailing 1

     

    Format: This one-day course is offered from 9:00 AM to 3:00 PM.

     

    Click the REGISTER button to view complete course information and reserve your place.

  • ASA 101 Keelboat 1 | July 10th & July 11th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to become a sailor? ASA 101 Keelboat Sailing 1 is the perfect place to begin. No previous sailing experience is required.

     

    Over one hands-on weekend, you’ll learn the fundamentals of sailing aboard a tiller-steered Hunter 216. With no more than four students per class, everyone receives plenty of time at the helm, trimming sails, practicing maneuvers, and rotating through the different crew positions.

     

    You’ll build a strong foundation in boat handling, sail trim, safety, sailing terminology, crew-overboard recovery, knots, and more, all while gaining the skills and confidence to continue your sailing journey.

     

    Your course includes two full days of hands-on sailing instruction aboard one of our training sailboats, use of all sailing equipment, the official ASA textbook and course materials, plus the ASA 101 examination and certification.

     

    Click the REGISTER button below to view the complete course details, available dates, and tuition, or reserve your place in an upcoming class.

  • ASA 103 Basic Coastal Cruising | July 22nd & 23rd, 2027 | Port Washington, WI: $897.00

    PORT WASHINGTON, WI
    Prerequisites: ASA 101 Keelboat Sailing 1

    Ready to move beyond the basics? ASA 103 Coastal Cruising builds on the foundation developed in ASA 101 and introduces you to the skills needed to safely operate a larger, auxiliary-powered cruising sailboat.

     

    During this intensive two-day course, you’ll gain hands-on experience with boat handling under sail and power, docking, sail trim, anchoring, navigation, weather, safety procedures, boat systems, and cruise preparation.


    By the end of the course, you’ll have greater confidence handling a cruising sailboat and a solid foundation for planning and enjoying daytime coastal cruises. You’ll also be prepared to continue building your skills with ASA 104: Bareboat Cruising.


    Format: This course is offered as an intensive two-day course.


    Click the REGISTER button to explore the complete course details, available dates, and tuition, or to reserve your place.

  • ASA 116: Dinghy and Outboard Endorsement | July 30th, 2027 | Milwaukee, WI: $497.00

    South Shore Yacht Club
    Prerequisites: Prerequisite: ASA 101 Keelboat Sailing 1

    The dinghy is an essential part of the cruising experience, serving as your transportation between the cruising boat, marina, anchorage and shore. ASA 116 Dinghy and Outboard Endorsement teaches you how to safely prepare, launch, operate, secure and care for a dinghy and its outboard motor.

     

    Through practical instruction, you’ll learn safe boarding, loading and handling; outboard setup and operation; maneuvering, docking and anchoring; basic maintenance and troubleshooting; and what to do when something does not go as planned.

     

    Prerequisite: ASA 101 Keelboat Sailing 1

     

    Format: This is a one-day course from 9:00am – 4:00pm. It combines instructor-led lessons with hands-on dinghy and outboard practice.

     

    Click the REGISTER button to view complete course information and reserve your place.

  • ASA 101 Keelboat 1 | August 7th & August 8th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to become a sailor? ASA 101 Keelboat Sailing 1 is the perfect place to begin. No previous sailing experience is required.

     

    Over one hands-on weekend, you’ll learn the fundamentals of sailing aboard a tiller-steered Hunter 216. With no more than four students per class, everyone receives plenty of time at the helm, trimming sails, practicing maneuvers, and rotating through the different crew positions.

     

    You’ll build a strong foundation in boat handling, sail trim, safety, sailing terminology, crew-overboard recovery, knots, and more, all while gaining the skills and confidence to continue your sailing journey.

     

    Your course includes two full days of hands-on sailing instruction aboard one of our training sailboats, use of all sailing equipment, the official ASA textbook and course materials, plus the ASA 101 examination and certification.

     

    Click the REGISTER button below to view the complete course details, available dates, and tuition, or reserve your place in an upcoming class.

  • Ales & Sails 5-Day Learn to Sail & Craft Beer Adventure along Lake Michigan’s Brewery Coast | August 9th through August 13th, 2027: $2,357.00

    South Shore Yacht Club
    Prerequisites: None

    Step aboard Calypso, our 41-foot Jeanneau Sun Odyssey, for five days and four nights of sailing, cruising, learning, and exploring. Ales & Sails combines an immersive liveaboard sailing course with a port-to-pint journey along Wisconsin’s Lake Michigan shoreline.

     

    By day, you’ll learn to sail while cruising from harbor to harbor and progressing through ASA 101 Keelboat Sailing 1, ASA 103 Coastal Cruising, and ASA 104 Bareboat Cruising. Under the guidance of Captain Don Doggett, USCG 100-Ton Master and American Sailing Senior Master Instructor, you’ll develop the practical skills and confidence needed to become an active, capable member of a cruising crew and begin taking command yourself.

     

    This is hands-on sailing. Students operate the boat, rotate through every crew position, and gradually assume responsibility for steering, sail handling, navigation, docking, anchoring, passage planning, crew coordination, decision-making, and serving as skipper.

     

    When the sailing day ends and Calypso is safely secured for the evening, it’s time to experience another Wisconsin tradition: craft beer.

     

    Our planned route takes us from South Shore Yacht Club in Milwaukee to Port Washington, Sheboygan, a night at anchor, and back to Milwaukee. Along the way, evenings may include brewery visits, local food, beer flights and tastings, plus a special Brews at Anchor evening featuring a selection of Wisconsin craft beers aboard Calypso.

     

    It’s a chance to experience what cruising is really about—not simply learning individual sailing skills, but living aboard, traveling under sail, arriving in a new port, exploring ashore, and waking up the next morning ready to do it all over again.

     

    By the end of the adventure, students who successfully complete the required examinations and practical skills assessments will have the opportunity to earn three internationally recognized American Sailing certifications: ASA 101, ASA 103, and ASA 104.

     

    Prerequisites: None. Previous sailing experience is not required.

     

    Format: Five-day liveaboard course from Monday, August 9th through Friday, August 13th, 2027. The exact sailing and brewery itinerary will be determined by weather, lake conditions, marina availability, and the captain’s judgment.

     

    Click the REGISTER button to explore the complete course details, cabin options, tuition, what to expect aboard, and book your spot.

    Five Days. Four Nights. Three ASA Certifications. Sail by day. Explore by night. Go home a certified sailor.

  • ASA 103 Basic Coastal Cruising | August 14th & 15th, 2027 | Port Washington, WI: $897.00

    PORT WASHINGTON, WI
    Prerequisites: ASA 101 Keelboat Sailing 1

    Ready to move beyond the basics? ASA 103 Coastal Cruising builds on the foundation developed in ASA 101 and introduces you to the skills needed to safely operate a larger, auxiliary-powered cruising sailboat.

     

    During this intensive two-day course, you’ll gain hands-on experience with boat handling under sail and power, docking, sail trim, anchoring, navigation, weather, safety procedures, boat systems, and cruise preparation.


    By the end of the course, you’ll have greater confidence handling a cruising sailboat and a solid foundation for planning and enjoying daytime coastal cruises. You’ll also be prepared to continue building your skills with ASA 104: Bareboat Cruising.


    Format: This course is offered as an intensive two-day course.


    Click the REGISTER button to explore the complete course details, available dates, and tuition, or to reserve your place.

  • ASA 111: Rules of the Road | August 20th, 2027 | Milwaukee, WI: $197.00

    South Shore Yacht Club
    Prerequisites: If certifying in ASA 111, ASA 101 Keelboat Sailing 1

    Know the rules before vessels meet on the water. This classroom-based ASA 111 Speciality Clinic course helps sailors understand and apply the Rules of the Road with greater confidence.

     


    Through practical examples and boating scenarios, you’ll learn how to determine which vessel is the stand-on vessel, which must give way and what actions should be taken during crossing, overtaking and head-on situations. The course also covers navigation lights, day shapes, sound signals, restricted visibility and the responsibilities shared by every vessel operator.

     

    Prerequisite: If certifying in ASA 111, ASA 101 Keelboat Sailing 1

     

    Format: This is a one-day course, 8:30am – 4:00pm, and is taught entirely on dry land in a classroom setting. There is no on-the-water portion.

     

    Click the REGISTER button to reserve your place.

Quote Icon

Doug and I took our first sailing lessons this past weekend and just wanted to let you know how much we enjoyed it.

Don and Ben were absolutely excellent in their teaching skills and presentation of the material. They were very easy to understand and reviewed all of the material thoroughly. We felt very comfortable out on the water as everything was explained in a matter we could understand being totally lay sailors! You have an awesome crew of instructors and just wanted you to let you know it was a wonderful experience and will highly recommend your sailing school to others.
- Doug & Mary C.

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