Step aboard Calypso, our 2014 Jeanneau Sun Odyssey 409, for a five-day liveaboard Learn-to-Sail Vacation built around a club-to-club cruise along Wisconsin’s Lake Michigan shoreline.

This immersive sailing experience combines ASA 101: Keelboat Sailing, ASA 103: Coastal Cruising, and ASA 104: Bareboat Cruising with something you simply can’t get in a traditional weekend sailing class: the experience of living aboard, traveling from port to port, and operating a genuine cruising sailboat as part of the crew.

You’ll eat, sleep, sail, navigate, dock, anchor, and help manage the boat throughout the week. Students rotate through every position aboard Calypso, and as skills and confidence develop, Captain Don increasingly steps back. Each student has opportunities to take the helm, direct the crew, make decisions, and serve as skipper while Captain Don coaches and steps in when necessary.

Along the way, you’ll also experience one of the great traditions of Great Lakes cruising: arriving at a yacht club as a visiting crew. You’ll help plan harbor approaches, prepare Calypso for guest docking, secure the boat for the evening, and then head ashore to experience the clubs and sailing communities along the Wisconsin shoreline.

Your Instructor

Your instructor 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 through our USCG-approved captain’s school, True North Maritime Academy.

Throughout the week, his role gradually changes from instructor to coach. The goal isn’t for you to watch Captain Don operate the boat. The goal is for you to learn to operate it.

What You’ll Learn

The week progresses naturally from fundamental sailing skills to coastal cruising and, ultimately, the responsibilities of planning and managing a multi-day cruise.

ASA 101 Keelboat Sailing 1

You’ll begin by building the fundamental skills necessary to understand, sail, and safely operate a keelboat, 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 the voyage progresses, you’ll transition to operating a larger auxiliary-powered cruising sailboat and begin developing the skills necessary to travel from port to port, including:

• 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 the voyage, managing the boat, and leading the crew. Topics and skills include:

• 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 voyage, students work with both traditional and electronic navigation. You’ll learn to understand what your instruments and chartplotter are telling you rather than simply following a line on a screen.

This Is Real Cruising

This isn’t five days of sailing in circles near the marina. Students should expect the majority of each day to revolve around sailing, boat handling, navigation, passage making, docking, anchoring, and the everyday responsibilities of operating a cruising sailboat.

Our planned Monday-through-Friday voyage begins and ends at South Shore Yacht Club in Milwaukee. From there, we’ll set out along Wisconsin’s Lake Michigan shoreline for a combination of sailing, an overnight at anchor, and visits to several yacht clubs and waterfront communities.

But this is real cruising, so our itinerary is intentionally flexible. Lake Michigan ultimately determines where we can safely go. Wind, waves, thunderstorms, visibility, marina availability, and other conditions may require us to alter the route, change destinations, or remain closer to port. That’s all part of the training!

Learning to evaluate conditions, modify a passage plan, select a safe alternative, and explain those decisions to your crew is an important part of becoming a capable cruising skipper.

The Yacht Club Experience

One of the highlights of this adventure is experiencing Lake Michigan’s yacht clubs from the perspective of a visiting cruising crew.

Before each arrival, students participate in reviewing harbor information, planning the approach, contacting the marina or club when appropriate, assigning crew responsibilities, preparing dock lines and fenders, and bringing Calypso safely into her guest berth.

Once the boat is secured and the day’s sailing responsibilities are complete, the evening becomes part of the vacation.

Head ashore with your crewmates for dinner or a drink, explore the waterfront, meet local sailors, and experience the traditions and camaraderie that make yacht clubs such an important part of the Great Lakes sailing community.

Depending on our final route, weather, guest policies, and club availability, planned stops may include South Shore Yacht Club, Milwaukee Yacht Club, Sheboygan Yacht Club, Racine Yacht Club, and other suitable destinations along the Wisconsin shoreline.

Along the way, we’ll also introduce you to yacht club traditions, burgees, guest etiquette, and the ways clubs connect sailors through cruising, racing, education, and social activities.

The exact clubs and experiences will vary based on our route, operating hours, guest policies, scheduled activities, and conditions during the week.

Prerequisites

No previous sailing experience or ASA certification is required.

Because the course combines three certification levels into five immersive days, students should arrive prepared for an active, fast-paced learning experience. Course books and online preparation materials are provided ahead of time so students can become familiar with the material before arriving.

Students should be comfortable moving around and living aboard a sailboat, participating in physical activities, working as part of a crew, and receiving coaching throughout the week.

Life Aboard Calypso

Calypso is a 2014 Jeanneau Sun Odyssey 409, a 41-foot modern cruising sailboat with three cabins and two heads. Living aboard gives students practical experience with the type of boat, accommodations, equipment, and onboard systems they may encounter as they progress toward independent cruising and bareboat chartering.

Bedding is provided, so students do not 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. A complete packing list will be emailed before the course.

Sea Safaris coordinates provisioning for the week. Each student should plan to contribute up to **$50 toward onboard provisions** and bring money for approximately three dinners ashore, personal purchases during yacht club visits, and any preferred snacks or beverages.

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 Dogget
• Use of Calypso and her sailing, navigation, and safety equipment
• Liveaboard accommodations and bedding
• Planned yacht club visits and guest-arrival experiences
• Pre-course logistics, packing information, and provisioning coordination

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.

Course Tuition & Cabin Options

• Private Cabin $3027.00
• Shared Cabin $2357.00
• Salon Berth (Shared Living Area) $1897.00

Students should also budget up to $50 for onboard provisions, approximately three dinners ashore, and any drinks or personal purchases during yacht club visits.

What You’ll Take Home

By Friday, you’ll have done considerably more than attend a sailing class.

You’ll have lived aboard a cruising sailboat, stood watches at the helm, trimmed sails, navigated Lake Michigan, docked in unfamiliar harbors, spent a night at anchor, arrived at yacht clubs as a visiting crew, helped manage a multi-day voyage, and taken your turn as skipper.

Students who successfully complete the written examinations and practical skills requirements can earn ASA 101, ASA 103, and ASA 104 certifications.

Those certifications represent an important milestone, but becoming a capable skipper takes continued experience. Graduates are encouraged to keep building time at the helm, practice docking and boat handling, and gain experience aboard progressively larger and more complex boats before independently chartering.