Ales & Sails 5-Day Learn to Sail & Craft Beer Adventure along Lake Michigan’s Brewery Coast | August 9th through August 13th, 2027
August 9 - 13 2027
$2357.00
Step aboard Calypso, our 41-foot Jeanneau Sun Odyssey 409, for five days and four nights of sailing, cruising, learning, and exploring Wisconsin’s Lake Michigan coast.
By day, you’ll learn to sail and operate a genuine cruising yacht while working toward ASA 101 Keelboat Sailing 1, ASA 103 Coastal Cruising, and ASA 104 Bareboat Cruising.
By evening, after Calypso is safely docked and the sailing day is complete, we’ll head ashore to experience another Wisconsin tradition, local craft beer! Our planned adventure takes us from South Shore Yacht Club in Milwaukee to Port Washington, Sheboygan, a night at anchor, and back to Milwaukee, combining serious hands-on sailing instruction with the fun of traveling from port to port aboard your own floating home.
Sail by day. Explore by night. Go home a certified sailor.
This Isn’t Just a Sailing Class
This trip is about learning how those skills come together when you actually go cruising. For five days, Calypso becomes your classroom, transportation, and home. You’ll sail from one destination to another, navigate the Lake Michigan shoreline, enter unfamiliar harbors, dock for the evening, live aboard, manage the boat’s systems and resources, spend a night at anchor, and wake up the next morning ready to do it again.
Students don’t simply watch the instructor operate the boat. You become the skippper in charge! Everyone rotates through the positions aboard Calypso. As the week progresses, Captain Don increasingly steps back and students take responsibility for steering, trimming sails, navigating, docking, anchoring, planning passages, directing the crew, making decisions, and ultimately serving as skipper.
Captain Don remains there to coach, teach, challenge your decisions, and intervene when necessary but the goal is to progressively put you in command. That’s where sailing skills begin turning into cruising confidence.
Your Port-to-Pint Adventure
Our planned five-day route follows Wisconsin’s Lake Michigan shoreline, with sailing and training during the day and a different experience waiting at the end of each passage.
Milwaukee → Port Washington
We depart South Shore Yacht Club and begin sailing north toward Port Washington. The first passage introduces the fundamentals of sailing while immediately putting those skills to work aboard a full-size cruising boat.
After securing Calypso in Port Washington for the evening, we’ll head ashore and celebrate our first passage with a visit to Inventors Brewpub, where the crew can enjoy dinner and sample a flight of locally brewed beer.
Port Washington → Sheboygan
The next morning, we continue north to Sheboygan. Students take on increasing responsibility for sail trim, steering, navigation, weather awareness, boat systems, crew coordination, and entering and departing harbors.
Once Calypso is secured for the evening, we’ll head over to 3 Sheeps Brewing for samples of Wisconsin craft beer and order pizza from a local favorite.
A Night at Anchor
One night, we’ll trade the marina for something every cruising sailor should experience: a night on the hook. Students will select an appropriate anchorage, determine depth and scope, prepare the ground tackle, deploy and set the anchor, verify that it’s holding, and learn how a cruising crew manages a boat overnight away from the dock. Once the boat is safely anchored and the day’s responsibilities are finished, we’ll break out our own selection of Wisconsin craft bottles for a special Brews at Anchor tasting aboard Calypso.
Dinner aboard. Sunset over the lake. A few interesting Wisconsin beers. And your sailboat swinging quietly on her anchor for the night. Now this is cruising!
Back to Milwaukee
Our final major passage brings us back south toward Milwaukee. By this point, students are doing far more than they were on Monday. You’ll be planning, navigating, handling the boat, communicating as a crew, evaluating conditions, and making many of the decisions necessary to get Calypso safely to her destination. After securing the boat near Milwaukee, our final planned brewery outing takes us to New Barons Brewing Cooperative, Wisconsin’s first cooperatively owned brewery, for one last evening together.
The following morning, we’ll make our final sail back to South Shore Yacht Club, complete remaining skills and assessments, and bring our Lake Michigan adventure to a close.
Our Port-to-Pint itinerary is weather dependent. Lake conditions, marina availability, brewery schedules, and the captain’s judgment may require destinations or evening activities to change. Learning when to change the plan is itself an important cruising skill.
Three ASA Certifications. One Continuous Experience.
Rather than treating ASA 101, 103, and 104 as three unrelated classes, this five-day format allows one skill to build naturally upon the next.
You begin by learning to sail, then you learn to operate a cruising sailboat. Finally, you learn to manage the cruise.
ASA 101: Keelboat Sailing
Your adventure begins with the fundamentals. You’ll develop the skills necessary to understand and operate a sailboat, including:
Sailing terminology and parts of the boat
Points of sail and wind direction
Raising, lowering, and trimming sails
Steering and maintaining a course
Tacking and jibing
Helm commands and crew communication
Crew-overboard prevention and recovery
Essential sailing knots, safety, and seamanship
ASA 103 Coastal Cruising
As your confidence grows, we’ll shift the focus from simply sailing the boat to operating a cruising sailboat. You’ll work with:
Cruising sailboat systems and equipment
Auxiliary engine operation
Maneuvering under sail and power
Docking, backing, and turning in confined areas
Using dock lines, fenders, and spring lines
Recognizing and aborting an unsuccessful docking approach
Reefing and sailing with reduced sail
Weather observation and interpretation
Paper charts, compass courses, and electronic navigation
Anchoring procedures and emergency response
ASA 104: Bareboat Cruising
During the latter portion of the week, you’ll take on greater responsibility for planning and managing the cruise, including:
- Passage and route planning
- Provisioning and living aboard
- Boat systems and routine maintenance
- Managing electrical power, water, and onboard resources
- Selecting an anchorage and calculating proper scope
- Deploying, setting, verifying, and retrieving the anchor
- Skipper responsibilities and decision-making
- Crew organization, communication, and leadership
- Preparing for and responding to emergencies
- Managing the vessel when assistance is not immediately available
Throughout the week, students work with both traditional and electronic navigation. You’ll learn to understand what your navigation equipment is telling you rather than simply following a line on a chartplotter.
Your Instructor
Your instructor for the week is Captain Don Doggett, a USCG 100-Ton Master, American Sailing Senior Master Instructor, and Instructor Evaluator.
Don brings more than 20 years of sailing and teaching experience on the Great Lakes, along with offshore and charter experience in Bermuda, the British Virgin Islands, Greece, and Croatia.
He teaches American Sailing courses through ASA 108: Offshore Passagemaking and also trains professional mariners pursuing their U.S. Coast Guard Captain’s Licenses through True North Maritime Academy, our USCG-approved captain’s school.
His approach aboard Calypso is straightforward: teach it, demonstrate it, coach you through it and then let you do it.
The objective isn’t to spend five days watching an experienced captain sail. It’s to start developing another one.
Life Aboard Calypso
For five days and four nights, Calypso is home.
She’s a 2014 Jeanneau Sun Odyssey 409, a modern 41-foot cruising sailboat with three cabins and two heads. You’ll be learning aboard the type of boat many sailors aspire to eventually own or charter.
Living aboard is part of the education.
You’ll learn how a cruising crew organizes the boat, manages water and electrical resources, provisions for a trip, keeps gear secure underway, prepares meals, maintains shared spaces, and settles into the daily rhythm of cruising.
Bedding is provided, so there’s no need to bring sleeping bags or linens.
Calypso does not have onboard heat. Students attending during cooler weather should bring layers, waterproof foul-weather gear, a warm hat and gloves, and non-marking shoes or sailing boots with good traction.
We’ll provide a complete packing list before departure so you’ll know exactly what to bring—and what to leave at home.
The Brewery Experience
Wisconsin has two pretty great traditions: boating and brewing. Ales & Sails brings them together.
After Calypso is safely docked or anchored and all sailing responsibilities for the day are finished, the crew can relax and enjoy the local community we’ve sailed to.
Our planned brewery experiences include stops in Port Washington, Sheboygan, and Milwaukee, along with our special Brews at Anchor tasting aboard Calypso.
These evenings aren’t intended to turn the trip into a drinking tour. They’re about enjoying the places we visit, sharing dinner with the crew, discovering some interesting Wisconsin beers, and experiencing the social side of cruising after a good day on the water.
Alcohol consumption is always optional. Non-alcoholic options are welcome, and all sailing and boat-handling activities are completed before the evening tasting or brewery visit begins.
No Sailing Experience? No Problem.
There are no sailing prerequisites for this trip. This fun Learn to Sail Vacation is designed to take you from the fundamentals of ASA 101 through the cruising skills of ASA 103 and ASA 104 during one immersive week.
It is, however, an active and fast-paced learning experience. We’ll send your ASA textbooks and provide access to online preparation materials before the trip. Students who spend some time with those materials before arriving can devote more of the week to actually sailing and practicing skills.
You should be comfortable moving around a sailboat, climbing aboard and ashore, participating in physical activities, living in shared quarters, working as part of a crew, and receiving coaching throughout the week.
You don’t need to arrive knowing how to sail. You do need to arrive ready to learn.
What’s Included
Course tuition includes:
- Five days of liveaboard sailing instruction
- ASA 101: Keelboat Sailing instruction
- ASA 103 Coastal Cruising instruction
- ASA 104 Bareboat Cruising instruction
- ASA textbooks and course materials mailed before class
- Access to online course-preparation materials
- ASA 101, ASA 103, and ASA 104 written examinations
- Practical skills instruction and assessments
- ASA 101, ASA 103, and ASA 104 certifications upon successful completion
- First-year American Sailing membership and ASID registration
- Instruction from Captain Don Doggett
- Use of Calypso and her sailing, navigation, and safety equipment
- Liveaboard accommodations and bedding
- Planned evening brewery visits in each port
- Pre-course logistics, packing information, and provisioning coordination
Course Tuition
- Private Cabin – Single Passenger = $3027.00 pp
- Shared Cabin = $2357.00 pp
- Salon Berth (Shared Living Area) = $1897.00 pp
In addition to tuition, budget up to $50 for onboard provisions, approximately three dinners ashore, and whatever you choose to purchase during brewery visits.
What Will You Take Home?
Hopefully, a few favorite beers. But much more importantly, you’ll leave with five days of genuine cruising experience that can’t be recreated in a classroom.
You’ll have sailed from port to port. You’ll have stood watch at the helm, trimmed sails, navigated Lake Michigan, maneuvered a 41-foot cruising boat, docked, anchored, lived aboard, worked as part of a crew, made decisions as skipper, and dealt with whatever conditions Lake Michigan gave us that week.
Students who successfully complete the written examinations and practical assessments will also have the opportunity to leave with ASA 101, ASA 103, and ASA 104 certifications.
Those certifications can help open the door to additional training, chartering, and eventually cruising on your own.
But earning three cards isn’t what makes this trip special.
The certifications are the result of the training. They are not the purpose of the training. The purpose is to start turning you into a sailor.
Five Days. Four Nights. Three ASA Certifications. Sail by day. Explore by night. Go home a certified sailor.
Ready to sail Wisconsin’s Brewery Coast? REGISTER NOW
