This is not just a sailing course. It is a hands-on Lake Michigan sailing adventure designed for students who want to learn, explore, and experience the rhythm of cruising life aboard a real sailboat.
Students sail along Wisconsin’s beautiful Lake Michigan shoreline, beginning in Milwaukee and visiting classic harbor towns such as Port Washington and Sheboygan. Along the way, they gain real-world sailing experience, practice coastal navigation, stand watches, assist with sail handling, help plan routes, and learn what it is like to live aboard a cruising sailboat.
Unlike a typical day-sailing class, this trip gives students a deeper and more memorable experience. They are not just learning isolated skills at the dock or in protected waters. They are applying those skills during an actual multi-day passage, with changing weather, harbor approaches, anchoring practice, meal planning, teamwork, and nights aboard.
The itinerary blends structured ASA sailing instruction with the relaxed feel of a Great Lakes getaway. Evenings may include marina stops, local dining, quiet nights aboard, harbor-town exploring, and, weather permitting, an unforgettable night at anchor along the shoreline.
Students leave with more than a certification. They leave with confidence, stories, new skills, and a real taste of the cruising lifestyle.
Students arrive at noon for check-in, boat orientation, safety briefing, provisioning review, and crew assignments. We depart Milwaukee at approximately 2:00 PM and sail north along the Lake Michigan shoreline toward Port Washington. Along the way, students will take part in sail handling, navigation, helm practice, lookout duties, and basic coastal cruising skills. Overnight in Port Washington.
After breakfast and a morning briefing, we depart Port Washington and continue north toward Sheboygan. This leg focuses on coastal navigation, watchkeeping, sail trim, docking preparation, and crew communication. Upon arrival in Sheboygan, students will have time to enjoy the harbor town, relax, and review the day’s sailing lessons. Overnight in Sheboygan.
We depart Sheboygan and sail south along the Wisconsin shoreline, practicing route planning, reefing decisions, weather awareness, and anchoring preparation. Weather permitting, we will anchor out for the night along the Lake Michigan shoreline, giving students the experience of setting the hook, monitoring the anchor, and enjoying a quiet night aboard under the stars.
After a morning briefing and breakfast aboard, we continue sailing along the Lake Michigan shoreline while wrapping up final course skills. This day is focused on refining boat handling, sail trim, crew coordination, docking preparation, navigation review, anchoring procedures, and overall confidence aboard a cruising sailboat. Depending on weather and itinerary, we may spend the night at anchor or in a nearby harbor.
On Friday morning, we complete the final sailing leg and return to Milwaukee by noon. The morning includes final skills review, boat cleanup, course debrief, and discussion of next steps in each student’s sailing journey. Students depart with hands-on experience in coastal cruising, navigation, anchoring, docking, and life aboard a cruising sailboat.
Please Note. This itinerary is meant to serve as an example, however, it is important to note that the actual itinerary is subject to change due to weather conditions or circumstances beyond our control.
I cannot recommend Don and Sea Safaris highly enough! I had an incredible experience sailing with Captain Don on his beautiful boat in Sturgeon Bay this past summer. During my time aboard, I completed ASA 103 (Basic Coastal Cruising) and ASA 104 (Bareboat Cruising).
Captain Don was a fantastic instructor—he tailored the lessons to my experience level, making the learning process both effective and enjoyable. His deep knowledge, technical expertise, and passion for sailing were evident throughout the trip. Beyond the instruction, he seamlessly combined expert training with the breathtaking beauty of sailing in Sturgeon Bay and Door County. It was truly an unforgettable experience!”
