Events
ASA 104, Bareboat Chartering | July 17th & July 18th, 2027 | Milwaukee, WI: $1,097.00
South Shore Yacht ClubPrerequisites: ASA101-Keelboat Sailing 1, ASA103-Coastal CruisingASA 104 Bareboat Cruising is a comprehensive cruising course for experienced sailors ready to take on greater responsibility aboard a larger cruising sailboat.
You’ll develop practical skills in basic navigation, cruise planning, provisioning, advanced anchoring techniques, boat systems, maintenance procedures, weather interpretation, and emergency response. You’ll also explore international sailing considerations and learn how to respond to the “what ifs” that might occur when you are away from immediate assistance and become the first responder for your boat and crew.
By the end of the course, you’ll be better prepared to act as skipper or crew aboard a 30- to 45-foot sailboat during a multi-day cruise in inland or coastal waters. Most charter companies require a sailing resume from the skipper and look for an internationally recognized certification such as ASA 104 when evaluating qualifications to charter a boat.ASA 104 also provides a strong foundation for continuing to ASA 105 Coastal Navigation and ASA 106 Advanced Coastal Cruising.
Format: This course is 2 consecutive days with and optional overnight. Students who successfully complete the required written examination and practical skills assessment will earn the ASA 104 certification.
Click the REGISTER button to explore the complete course details, tuition, and to reserve your place in this class.
![ASA 104, Bareboat Chartering]( "ASA 104, Bareboat Chartering")
ASA 108, Offshore Passage Making | July 19th through July 23rd, 2027 | Milwaukee, WI: $3,427.00
South Shore Yacht ClubPrerequisites: ASA 106 Advanced Coastal Cruising, ASA 107: Celestial Navigation or ASA 117: Basic Celestial EndorsementStep up to true offshore sailing with Sea Safaris’ ASA 108: Offshore Passagemaking course, departing from South Shore Yacht Club in Milwaukee.
This advanced five-day liveaboard course is designed for experienced sailors who want to confidently plan and execute multi-day, nonstop passages while sailing day and night away from the comfort of the marina.
You’ll stand watches, sail through the night, and rotate through the roles of skipper, watch captain, navigator, helmsman, and crew. Along the way, you’ll gain real-world experience with passage planning, weather routing, nighttime navigation, heavy-weather preparation, emergency procedures, and managing a vessel underway.
The passage is planned to include at least 72 continuous hours and 100 nautical miles without touching land, providing genuine offshore passagemaking experience, not simply a series of day sails. Students who successfully complete the course requirements will earn the ASA 108 certification.
Prerequisites: ASA 106 Advanced Coastal Cruising and either ASA 107: Celestial Navigation or ASA 117: Basic Celestial Endorsement.
Format: Five-day liveaboard course departing from and returning to South Shore Yacht Club in Milwaukee. The exact route and passage schedule will be determined by weather, lake conditions, and the captain’s judgment.
Click the REGISTER button to explore the complete course details, tuition, and to reserve your place aboard.
![ASA 108, Offshore Passagemaking]( "ASA 108, Offshore Passagemaking")
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 111: Anchoring Skills Clinic | August 6th, 2027 | South Shore Yacht Club, Milwaukee, WI: $425.00
South Shore Yacht ClubPrerequisites: ASA 101 Keelboat Sailing 1, ASA 103 Coastal Cruising recommendedMaster one of the most important cruising skills during this hands-on ASA 111 Speciality Clinic focused entirely on anchoring.
You’ll learn how to select a suitable anchorage, evaluate wind, current, depth and bottom conditions, calculate proper scope, set and test the anchor, monitor your position and safely retrieve the anchor when it is time to depart. Whether you are preparing for a bareboat charter, planning longer cruising adventures or simply want greater confidence as skipper, this clinic provides practical experience you can use on the water.
Prerequisite: ASA 101 Keelboat Sailing 1, ASA 103 Coastal Cruising recommended
Format: This one-day course is offered from 9:00 AM to 4:00 PM.
Click the REGISTER button to view complete course information and reserve your place.
![ASA111, Sailing Skills Review]( "ASA111, Sailing Skills Review")
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 105/106 – Lake Michigan Advanced Coastal Navigation & Cruising | August 16th through August 20th, 2027 | Port Washington, WI: $3,057.00
PORT WASHINGTON, WIPrerequisites: ASA 101 – Basic Keelboat Sailing, ASA 103 – Basic Coastal Cruising, ASA 104 – Bareboat CruisingLearn the navigation at home. Then cross Lake Michigan and put it to work.
The ASA 105/106 Lake Michigan Advanced Coastal Navigation and Cruising course combines the convenience of online ASA 105 instruction with an intensive five-day advanced cruising passage across Lake Michigan.
Before departure, you’ll complete the ASA 105 Coastal Navigation course online at your own pace. You’ll then apply those skills aboard a fully equipped cruising sailboat by helping plan, plot, and navigate a real passage from Port Washington to the Michigan shoreline and back.
Throughout the voyage, you’ll rotate through the responsibilities of skipper, navigator, helmsman, lookout, and watchstander. Training includes traditional chart plotting, electronic navigation, passage planning, day and nighttime sailing, watchkeeping, weather analysis, advanced sail handling, heavy-weather preparation, emergency procedures, vessel systems, and crew leadership.
By the end of the course, you’ll have experience applying advanced navigation and seamanship skills during an extended Great Lakes passage. Students who successfully complete the required knowledge examinations and practical skills assessments will earn both ASA 105 Coastal Navigation and ASA 106 Advanced Coastal Cruising certifications.
Prerequisites: Students entering ASA 106 should hold ASA 101: Keelboat Sailing, ASA 103 Coastal Cruising, and ASA 104 Bareboat Cruising certifications.
Format: Complete the online ASA 105 learning portion before departure, followed by a five-day onboard passage from August 16th through August 20th, 2027. The planned passage departs from Port Washington, crosses Lake Michigan to the Michigan shoreline, and returns to Port Washington. Weather, wind, and sea conditions will determine the exact destination and passage schedule.
Click the REGISTER button to explore the complete course details, passage plan, tuition, and available dates, or to reserve your place aboard.
Five Days. Two Advanced ASA Certifications. One Lake Michigan Passage.
![ASA 105/106 combo class]( "asa-105-106-combo")
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 104, Bareboat Chartering | August 21st & August 22nd, 2027 | Milwaukee, WI: $1,097.00
South Shore Yacht ClubPrerequisites: ASA101-Keelboat Sailing 1, ASA103-Coastal CruisingASA 104 Bareboat Cruising is a comprehensive cruising course for experienced sailors ready to take on greater responsibility aboard a larger cruising sailboat.
You’ll develop practical skills in basic navigation, cruise planning, provisioning, advanced anchoring techniques, boat systems, maintenance procedures, weather interpretation, and emergency response. You’ll also explore international sailing considerations and learn how to respond to the “what ifs” that might occur when you are away from immediate assistance and become the first responder for your boat and crew.
By the end of the course, you’ll be better prepared to act as skipper or crew aboard a 30- to 45-foot sailboat during a multi-day cruise in inland or coastal waters. Most charter companies require a sailing resume from the skipper and look for an internationally recognized certification such as ASA 104 when evaluating qualifications to charter a boat.ASA 104 also provides a strong foundation for continuing to ASA 105 Coastal Navigation and ASA 106 Advanced Coastal Cruising.
Format: This course is 2 consecutive days with and optional overnight. Students who successfully complete the required written examination and practical skills assessment will earn the ASA 104 certification.
Click the REGISTER button to explore the complete course details, tuition, and to reserve your place in this class.
![ASA 104, Bareboat Chartering]( "ASA 104, Bareboat Chartering")
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")
