Skip to content

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!

Beginner

Events

Events Search and Views Navigation

Event Views Navigation

Today

Filters

Changing any of the form inputs will cause the list of events to refresh with the filtered results.

  • ASA 103 Basic Coastal Cruising | June 1st – June 3rd | South Shore Yacht Club, Milwaukee, WI: $1,497.00

    South Shore Yacht Club
    Prerequisites: ASA 101 Keelboat 1

    This course is the next step into 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 28 – 35 feet in length, in moderate winds and sea conditions. You will learn the basics of daytime coastal cruising in moderate wind and sea conditions including the recommended safety equipment, forecasting weather, reading navigational charts, marlinspike seamanship, boat handling under sail and power and more.

    Over several days you’ll eat, sleep, and sail on the water while building real cruising confidence.

    Format: 3 Day Live-aboard.

    Register
    ASA 103, Basic Coastal Cruising

  • A Learn-To-Sail Vacation on Lake Michigan – June 8th -12th, 2026:

    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.

    Register
    ASA 103/104 combo class

  • ASA 101 Keelboat 1 | June 20th & 21st | 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
    Register
    ASA 101, Basic Keelboat Sailing

  • 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
    Register
    ASA 101, Basic Keelboat Sailing

  • ASA 103 Basic Coastal Cruising | July 13th – July 15th | South Shore Yacht Club, Milwaukee, WI: $1,497.00

    South Shore Yacht Club
    Prerequisites: ASA 101 Keelboat 1

    This course is the next step into 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 28 – 35 feet in length, in moderate winds and sea conditions. You will learn the basics of daytime coastal cruising in moderate wind and sea conditions including the recommended safety equipment, forecasting weather, reading navigational charts, marlinspike seamanship, boat handling under sail and power and more.

    Over several days you’ll eat, sleep, and sail on the water while building real cruising confidence.

    Format: 3 Day Live-aboard.

    Register
    ASA 103, Basic Coastal Cruising

  • 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
    Register
    ASA 101, Basic Keelboat Sailing

  • A Learn-To-Sail Vacation on Lake Michigan – August 17th -21st, 2026:

    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.

    Register
    ASA 103/104 combo class

  • A Learn-To-Sail Vacation on Lake Michigan – September 7th -11th, 2026:

    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.

    Register
    ASA 103/104 combo 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.

Add More Adventure to your inbox!

Join our email list to be the first to get info on classes, charters, and flotillas to maximize fun and learning on the water.

Sign me up!

Join our email list: