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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 101 Keelboat 1 | July 11th & 12th | South Shore Yacht Club, Milwaukee, WI: $597.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to embark on your sailing journey? This course is the perfect starting point for anyone looking to learn the art of sailing. You’ll gain the essential skills and confidence needed to sail a 20-foot boat in light to moderate winds and calm waters without the need for supervision.

    Throughout this comprehensive course, you’ll dive into the fundamentals of keelboat sailing, including:

    • Sail theory and hands-on practice
    • Navigating common sailing terminology
    • Key safety equipment and procedures
    • Crew overboard recovery techniques
    • Mastering essential sailing knots
    • And much more!

    By the end of the course, you’ll be equipped with the knowledge to confidently handle a boat and enjoy time on the water.

    Course Format:
    This course is offered as a 2 day weekend course over Saturday and Sunday.

    • Saturday 8:30am – 2:30pm
    • Sunday 8:30am – 2:30pm
  • ASA 101/103 Basic Sailing & Basic Cruising Combo | July 22nd – July 24th | Port Washington, WI: $1,357.00

    PORT WASHINGTON, WI
    Prerequisites: None

    ASA101 – This is a perfect course for students with fundamental sailing knowledge. Because of the shortened format, the course moves along quickly. The Basic Keelboat will be a refresher as much as learning new skills. It will provide the necessary knowledge to sail a boat of about 20 feet in light to moderate winds and sea conditions in familiar waters without supervision. The course is taught by USCG Captains and your certification is recognized by the United States Coast Guard as a Safe Boating Course.

    ASA103 – General Description: This course is the next step and serves as an introductory course to the world of coastal cruising. It provides the necessary knowledge to cruise safely in local and regional waters as both skipper and crew on an auxiliary powered sailboat of about 30 – 35 feet in length, in moderate winds and sea conditions.

    Format: This course is offered as a 3 day course over Wednesday, Thursday, and Friday, 8 hours each day.

    Wednesday, July 22nd, 2026 (8:30 am – 4:30 pm)
    Thursday, July 23rd, 2026 (8:30 am – 4:30 pm)
    Friday, July 24th, 2026 (8:30 am – 4:30 pm)

  • ASA 101 Keelboat 1 | August 1st & 2nd | South Shore Yacht Club, Milwaukee, WI: $597.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to embark on your sailing journey? This course is the perfect starting point for anyone looking to learn the art of sailing. You’ll gain the essential skills and confidence needed to sail a 20-foot boat in light to moderate winds and calm waters without the need for supervision.

    Throughout this comprehensive course, you’ll dive into the fundamentals of keelboat sailing, including:

    • Sail theory and hands-on practice
    • Navigating common sailing terminology
    • Key safety equipment and procedures
    • Crew overboard recovery techniques
    • Mastering essential sailing knots
    • And much more!

    By the end of the course, you’ll be equipped with the knowledge to confidently handle a boat and enjoy time on the water.

    Course Format:
    This course is offered as a 2 day weekend course over Saturday and Sunday.

    • Saturday 8:30am – 2:30pm
    • Sunday 8:30am – 2:30pm
  • ASA 101 Keelboat 1 | August 15th & 16th | South Shore Yacht Club, Milwaukee, WI: $597.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to embark on your sailing journey? This course is the perfect starting point for anyone looking to learn the art of sailing. You’ll gain the essential skills and confidence needed to sail a 20-foot boat in light to moderate winds and calm waters without the need for supervision.

    Throughout this comprehensive course, you’ll dive into the fundamentals of keelboat sailing, including:

    • Sail theory and hands-on practice
    • Navigating common sailing terminology
    • Key safety equipment and procedures
    • Crew overboard recovery techniques
    • Mastering essential sailing knots
    • And much more!

    By the end of the course, you’ll be equipped with the knowledge to confidently handle a boat and enjoy time on the water.

    Course Format:
    This course is offered as a 2 day weekend course over Saturday and Sunday.

    • Saturday 8:30am – 2:30pm
    • Sunday 8:30am – 2:30pm
  • A Learn-To-Sail Vacation on Lake Michigan – August 17th -21st, 2026: $1,797.00

    South Shore Yacht Club
    Prerequisites: None

    During your liveaboard experience, you’ll have the opportunity to earn these internationally recognized ASA certifications:

    • ASA 101 – Basic Keelboat Sailing

    • ASA 103 – Basic Coastal Cruising

    • ASA 104 – Bareboat Cruising

    Learn, relax, and explore—then head home as a certified sailor ready for your next voyage.

  • ASA 101 Keelboat 1 | September 5th & 6th | South Shore Yacht Club, Milwaukee, WI: $597.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to embark on your sailing journey? This course is the perfect starting point for anyone looking to learn the art of sailing. You’ll gain the essential skills and confidence needed to sail a 20-foot boat in light to moderate winds and calm waters without the need for supervision.

    Throughout this comprehensive course, you’ll dive into the fundamentals of keelboat sailing, including:

    • Sail theory and hands-on practice
    • Navigating common sailing terminology
    • Key safety equipment and procedures
    • Crew overboard recovery techniques
    • Mastering essential sailing knots
    • And much more!

    By the end of the course, you’ll be equipped with the knowledge to confidently handle a boat and enjoy time on the water.

    Course Format:
    This course is offered as a 2 day weekend course over Saturday and Sunday.

    • Saturday 8:30am – 2:30pm
    • Sunday 8:30am – 2:30pm
  • 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.

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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