Your learn-to-sail vacation begins in Milwaukee, Wisconsin, where we depart from the city’s well-protected harbor and slip past the breakwater into the open waters of Lake Michigan. From there, we sail north along Wisconsin’s scenic shoreline, making memorable stops in Port Washington, Sheboygan, and other nearby ports of call as conditions and crew goals allow. This “port-to-port” format turns every day into a mini-adventure. Real coastal-style sailing with the comfort of multiple safe harbors close at hand.
Lake Michigan is an ideal classroom because it offers true big-water sailing without the complexity of ocean tides and currents. Expect a mix of conditions that build skill quickly: steady winds that let you practice sail trim and boat handling, and wave patterns that teach timing, balance, and smart decision-making. You’ll learn how to plan a passage, read the weather, manage comfort and safety underway, and enter unfamiliar harbors with calm confidence—skills that transfer anywhere you sail next.
Trade the usual “sit-on-the-beach” getaway for a hands-on sailing vacation on Lake Michigan. Over five days aboard Calypso, a comfortable Jeanneau 409, you’ll learn real-world sailing skills while exploring Milwaukee’s waterfront and the open water just beyond the breakwall. This is a learn-by-doing experience: you’ll take the helm, trim sails, practice maneuvers, and build confidence day by day with coaching tailored to your pace.
You’ll cover the core fundamentals of sailing—points of sail, sail trim, steering to wind and waves, tacking and jibing, basic docking and close-quarters boat handling, anchoring, man-overboard procedures, knot-tying, rules of the road, weather awareness, and safety systems. Expect a smart mix of instruction, practice time, and “this is why it matters” coaching that helps everything click.
Perfect for first-time sailors, couples, or adventurous travelers who want a skill-based vacation, this course blends training with the kind of lake time people come to Lake Michigan for: big-water sailing, fresh air, and sunsets that feel like they were made for a cockpit.
Who it’s for: Beginners and motivated novices (no experience required)
What you’ll leave with: Practical sailing confidence, stronger seamanship, and a week of memories that beat another resort wristband.
Just as important, this trip is designed to feel like a vacation. Each stop offers time ashore to recharge and explore. In Port Washington, enjoy a relaxed waterfront vibe. Perfect for an easy stroll through town after docking, grabbing coffee or ice cream, and soaking up classic Lake Michigan harbor charm. In Sheboygan, you’ll find a lively lakeside scene with great dining options. An ideal place to celebrate the day’s progress, swap stories from the cockpit, and enjoy a well-earned meal before turning in aboard Calypso.
By combining hands-on instruction with beautiful destinations, this route delivers the best of both worlds: serious skill-building on the water, and great lake-town experiences at every port.
Captain Don Doggett, USCG 100 Master Captain and ASA Sailing Instructor with 20 years of experience operating various power and sailboats. Blue water and near coastal experience. Sailing experience typically teaching on monohulls and catamarans 40’ to 50′. Recent ports of call include Bermuda, BVI, Croatia, Greece, Grenada, Lake Michigan, Lake Superior, Sint Maarten, St Petersburg, Florida, and USVI.
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.
The time spent on and off the water was amazing. Our Captain was fantastic and made the adventure stress-free. We had an amazing sailing vessel, in fantastic shape, and extremely clean. The trip was well laid out, the nights were fun and relaxing as we enjoyed sleeping aboard and looking up at the stars. Sea Safaris did a great job. I’m already planning my trip for next year. Thanks again for organizing and hosting.
