Intermediate
Events
ASA 118 Docking Endorsement | June 25th | South Shore Yacht Club, Milwaukee, WI: $697.00
Take the stress and uncertainty out of docking with ASA 118 Docking Endorsement.
This hands-on course combines docking theory with repeated practice to help you confidently maneuver, dock, and cast off an auxiliary-powered sailboat. You’ll learn how wind, current, prop walk, pivot point, and boat configuration affect your approach, then practice using dock lines, spring lines, fenders, and crew communication in a variety of situations.
Training also includes harbor maneuvering, controlled stops, backing, turning within narrow fairways, and handling the boat in confined or busy areas. The techniques apply to everything from 30-foot weekend cruisers to 50-foot, single-screw sailing yachts.
Both newly certified and experienced sailors can benefit from focused docking practice. Skippers, spouses, partners, and crew members will leave better prepared to contribute during docking and more confident aboard the boat.
Prerequisites: ASA 103 Coastal Cruising or equivalent experience handling an auxiliary-powered sailboat.
Format: This is a hands-on, on-the-water, one-day course from 9:00am – 4:00pm
Click the REGISTER button to explore the complete course details, and to reserve your place aboard.
![ASA118 – Docking Endorsement (118)]( "ASA118 – Docking Endorsement (118)")
ASA 103/104 – Lake Michigan Intensive Learn-to-Sail Adventure – Coastal to Bareboat Cruising Combo | July 5th through July 9th, 2027 | Port Washington, WI: $2,457.00
PORT WASHINGTON, WIPrerequisites: ASA 101 Keelboat Sailing 1Turn five days on Lake Michigan into the sailing experience that takes you from basic sailing skills to confidently cruising a larger sailboat.
The ASA 103/104 Lake Michigan Intensive Learn-to-Sail Adventure combines two American Sailing certifications with a five-day liveaboard cruising experience along Wisconsin’s Lake Michigan shoreline.
Rather than returning to the same marina after each lesson, we’re going cruising. You’ll depart Port Washington, sail north to Sheboygan and Manitowoc, practice anchoring and living aboard away from marina facilities, and work your way back to Port Washington.
Throughout the voyage, you’ll become an active member of the crew while rotating through sailing, navigation, docking, anchoring, passage planning, boat systems, weather decisions, and skipper responsibilities. The goal is not simply to pass two ASA courses. It is to experience what it is actually like to plan, sail, and manage a multi-day cruise aboard a larger cruising sailboat.
By the end of the adventure, students who successfully complete the required examinations and practical skills assessments will earn both ASA 103 Coastal Cruising and ASA 104 Bareboat Cruising certifications.
Prerequisite: ASA 101: Keelboat Sailing 1
Format: Monday, July 5th through Friday, July 9th, 2027, departing from and returning to Port Washington. The planned route is Port Washington to Sheboygan, Manitowoc, an anchorage, and back to Port Washington. The exact itinerary may change based on weather, wind, lake conditions, and the captain’s judgment.
Click the REGISTER button to explore the complete course details, itinerary, tuition, and to reserve your place aboard.
Five Days. Two ASA Certifications. One Lake Michigan Cruising Adventure.
![ASA 103/104 combo class]( "asa-103-104-combo")
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 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")
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 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")
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")
