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Sail With Confidence!

Signing up for sailing lessons has never been this easy! Now is the time to sign up, get out on the water and earn your ASA Sailing Certification with America's favorite sailing school! Our course line up covers everything from Basic Sailing to Cruising to Advanced Navigation, Flotillas, Group Events and more.

Use the filters on the left to search for Beginner, Intermediate and Advanced classes.

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  • 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 106 Advanced Coastal Cruising | August 24th – 28th | South Shore Yacht Club, Milwaukee, WI: $3,197.00

    South Shore Yacht Club
    Prerequisites: ASA 104 Bareboat Cruising and ASA 105 Coastal Navigation

    This course equips participants with the essential knowledge and skills to safely operate as the skipper and crew of a sailing vessel ranging from 30 to 50 feet in length. It encompasses both day and nighttime sessions conducted in coastal and inland waters, regardless of weather conditions. Building upon the foundations laid in prior ASA courses, students embark on an extended coastal sail, including overnight passages, where they will learn new concepts and apply advanced sailing techniques and skills.

    The course spans five days and imparts the prequisite expertise for coastal navigation. It instills the confidence to plan, chart, and execute extended coastal cruises under varying conditions on sailboats of up to 50 feet in length.

    Sailing Vessel – 2014 Jeanneau 409 Sun Odyssey
    This is an attractive 40 foot sailing yacht, is designed with 3 cabins and 2 heads. This is a top of the line cruising model with all of the comforts and features to make learning fun and safe. Features include: Roller furling sails, dodger and bimini, anchor windlass, autopilot, GPS, and color chartplotter.

    Note: If you haven’t yet completed your ASA 105 (Coastal Navigation) certification, we recommend enrolling in our online ASA 105 course through Sea Safaris Online. You’ll have the option to complete the final exam during the sailing trip.

  • 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 111: Anchoring Skills Clinic | September 27th | South Shore Yacht Club, Milwaukee, WI: $397.00

    South Shore Yacht Club
    Prerequisites: ASA 101 Keelboat Sailing 1

    Master one of the most important cruising skills with this hands-on ASA 111 Sailing Review course focused exclusively on anchoring.

    Whether you’re preparing for a bareboat charter, planning extended cruising adventures, or simply looking to improve your confidence as skipper, this practical clinic will teach you how to anchor safely, confidently, and effectively in a variety of conditions.

    During this course, students will review anchoring equipment and techniques, learn how to select suitable anchorages, evaluate depth, wind, and bottom conditions, calculate proper scope, set and test an anchor, and safely depart an anchorage. Students will also discuss common anchoring challenges, overnight considerations, and strategies for preventing dragging and other anchoring issues.

    Topics include:

    • Types of anchors and ground tackle
    • Selecting a safe anchorage
    • Wind, current, depth, and bottom considerations
    • Calculating and deploying proper scope
    • Setting and verifying anchor holding
    • Anchor watch procedures
    • Retrieving and stowing the anchor
    • Communication and crew coordination
    • Common anchoring mistakes and troubleshooting

    This ASA 111 Sailing Review clinic combines classroom discussion with extensive on-the-water practice to help sailors develop the skills and confidence needed to anchor independently.

    Format: This course is offered as a 1-day course, 9:00 AM – 4:00 PM each day.

    Prerequisites: ASA 101 Keelboat Sailing 1

    Certification: ASA 111 Sailing Review

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