Beginner
Events
ASA 103 Basic Coastal Cruising | July 22nd & 23rd, 2027 | Port Washington, WI: $897.00
PORT WASHINGTON, WIPrerequisites: ASA 101 Keelboat Sailing 1Ready 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 103, Basic Coastal Cruising]( "ASA 103, Basic Coastal Cruising")
ASA 116: Dinghy and Outboard Endorsement | July 30th, 2027 | Milwaukee, WI: $497.00
South Shore Yacht ClubPrerequisites: Prerequisite: ASA 101 Keelboat Sailing 1The 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-116")
ASA 101 Keelboat 1 | August 7th & August 8th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00
South Shore Yacht ClubPrerequisites: NoneReady 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, Basic Keelboat Sailing]( "ASA 101, Basic Keelboat Sailing")
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 ClubPrerequisites: NoneStep 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.
![]( "Ales and Sails – asa 101-103-104 LTS")
ASA 103 Basic Coastal Cruising | August 14th & 15th, 2027 | Port Washington, WI: $897.00
PORT WASHINGTON, WIPrerequisites: ASA 101 Keelboat Sailing 1Ready 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 103, Basic Coastal Cruising]( "ASA 103, Basic Coastal Cruising")
ASA 111: Rules of the Road | August 20th, 2027 | Milwaukee, WI: $197.00
South Shore Yacht ClubPrerequisites: If certifying in ASA 111, ASA 101 Keelboat Sailing 1Know 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.
![ASA111, Sailing Skills Review]( "ASA111, Sailing Skills Review")
ASA 111: Bareboat Chartering Workshop | September 3rd, 2027 | Milwaukee, WI: $197.00
Stop Dreaming About a Bareboat Charter. Start Planning One.
Chartering a sailboat for a week can be one of the best sailing adventures you’ll ever have but there’s a lot more to a successful charter than choosing a beautiful destination and reserving a boat.
ASA 111 Bareboat Chartering Workshop takes you through the real-world decisions that happen before you ever step aboard. You’ll learn how to choose a destination, evaluate charter companies and boats, build a realistic itinerary, provision for the trip, prepare your crew, and avoid many of the mistakes that can turn an expensive sailing vacation into a stressful one.
We’ll also tackle one of the biggest questions first-time charter skippers have: “Am I actually qualified to charter this boat?” You’ll learn what charter companies look for on a sailing resume, how to present your experience, and what to expect during charter check-in, the boat briefing, and your pre-departure inspection.
Then we’ll get into the “what ifs.” What if the weather changes? Something aboard stops working? Your itinerary falls apart? A crew member gets sick or injured? When you’re cruising away from your home marina, you’re the skipper and your crew will be looking to you for answers.
This course is designed to help you arrive at the charter base prepared, organized, and ready to enjoy the adventure rather than figuring everything out as you go.
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.
![ASA111, Sailing Skills Review]( "ASA111, Sailing Skills Review")
ASA 101 Keelboat 1 | September 4th & September 5th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00
South Shore Yacht ClubPrerequisites: NoneReady 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, Basic Keelboat Sailing]( "ASA 101, Basic Keelboat Sailing")
Burgees & Breezes 5-Day Learn to Sail & Lake Michigan Sailing & Yacht Club Adventure | September 6th through September 10th, 2027: $2,357.00
South Shore Yacht ClubPrerequisites: NoneStep aboard Calypso, our 41-foot Jeanneau Sun Odyssey, for a five-day liveaboard Learn-to-Sail Vacation built around one of the great traditions of Great Lakes sailing: cruising from yacht club to yacht club along Wisconsin’s Lake Michigan shoreline.
For five days, Calypso becomes your classroom—and your home. You’ll eat, sleep, and sail aboard a modern cruising yacht while progressing through ASA 101: Keelboat Sailing, 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 move well beyond simply riding along. You become the skipper in charge.
Students rotate through every position aboard the boat and progressively take responsibility for steering, sail handling, navigation, docking, anchoring, boat systems, crew communication, decision-making, and ultimately serving as skipper. As your skills develop, Captain Don increasingly steps back, allowing you and your crewmates to operate the boat while he coaches, teaches, and steps in when necessary.
Along the Way we’ll explore a Different Port and a new Yacht Club
The adventure begins at South Shore Yacht Club in Milwaukee, where you’ll get acquainted with Calypso, your crew, and the fundamentals of sailing before heading out onto Lake Michigan.
During the week, the crew will experience both a night at anchor and overnight stops at several Wisconsin yacht clubs, with a planned route that may include Sheboygan Yacht Club, Milwaukee Yacht Club, Racine Yacht Club, and our home port at South Shore Yacht Club.
Each destination adds another dimension to the adventure. You’ll plan passages, navigate into unfamiliar harbors, communicate with marinas, secure Calypso in a guest slip, and experience the traditions and camaraderie of the Lake Michigan yacht club community.
And when the boat is secured and the day’s sailing is finished, you’re already at the club. Head ashore with your crewmates, grab dinner or a drink, meet local sailors, explore the waterfront, and enjoy a side of cruising that you simply can’t experience in a traditional weekend sailing class.
By Friday, you’ll have done much more than take sailing lessons. You’ll have lived aboard, cruised Lake Michigan, visited multiple ports, experienced the yacht club circuit, and taken your turn running a genuine cruising sailboat.
Students who successfully complete the required examinations and practical skills assessments will have the opportunity to earn three American Sailing certifications: ASA 101, ASA 103, and ASA 104.
Prerequisites: None. Previous sailing experience is not required.
Format: Five-day liveaboard sailing adventure, Monday, September 6th through Friday, September 10th, 2027. Because this is real cruising, the exact route and yacht club stops may change based on weather, lake conditions, marina availability, club schedules, and the captain’s judgment.
Click the REGISTER button to explore the complete itinerary, cabin options, tuition, what life aboard Calypso is really like, and to book your spot.
Five Days. Three ASA Certifications. Four Lake Michigan Yacht Clubs. One Unforgettable Sailing Adventure.
![]( "Burgees and Breezes – asa 101-103-104")
ASA 103 Basic Coastal Cruising | September 9th & 10th, 2027 | Port Washington, WI: $897.00
PORT WASHINGTON, WIPrerequisites: ASA 101 Keelboat Sailing 1Ready 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 103, Basic Coastal Cruising]( "ASA 103, Basic Coastal Cruising")
