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Signing up for sailing lessons has never been this easy! Now is the time to sign up, get out on the water and earn your ASA Sailing Certification with America's favorite sailing school! Our course line up covers everything from Basic Sailing to Cruising to Advanced Navigation, Flotillas, Group Events and more.

Use the filters on the left to search for Beginner, Intermediate and Advanced classes.

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  • ASA 103 Basic Coastal Cruising | August 13th & August 14th | Port Washington, WI: $927.00

    PORT WASHINGTON, WI
    Prerequisites: ASA 101 Basic Keelboat Sailing

    This course is the next step into the world of coastal cruising. It provides the necessary knowledge to cruise safely in local and regional waters as both skipper and crew on an auxiliary powered sailboat of about 28 – 35 feet in length, in moderate winds and sea conditions. You will learn the basics of daytime coastal cruising in moderate wind and sea conditions including the recommended safety equipment, forecasting weather, reading navigational charts, marlinspike seamanship, boat handling under sail and power and more.

    Format: This course is offered as a 2 day course over Thursday and Friday.

    Thursday, August 13th, 2026 (8:30 am – 4:30 pm)
    Friday, August 14th, 2026 (8:30 am – 4:30 pm)

  • ASA 101 Keelboat 1 | August 15th & 16th | South Shore Yacht Club, Milwaukee, WI: $597.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to embark on your sailing journey? This course is the perfect starting point for anyone looking to learn the art of sailing. You’ll gain the essential skills and confidence needed to sail a 20-foot boat in light to moderate winds and calm waters without the need for supervision.

    Throughout this comprehensive course, you’ll dive into the fundamentals of keelboat sailing, including:

    • Sail theory and hands-on practice
    • Navigating common sailing terminology
    • Key safety equipment and procedures
    • Crew overboard recovery techniques
    • Mastering essential sailing knots
    • And much more!

    By the end of the course, you’ll be equipped with the knowledge to confidently handle a boat and enjoy time on the water.

    Course Format:
    This course is offered as a 2 day weekend course over Saturday and Sunday.

    • Saturday 8:30am – 2:30pm
    • Sunday 8:30am – 2:30pm
  • A Learn-To-Sail Vacation on Lake Michigan – August 17th -21st, 2026: $1,797.00

    South Shore Yacht Club
    Prerequisites: None

    During your liveaboard experience, you’ll have the opportunity to earn these internationally recognized ASA certifications:

    • ASA 101 – Basic Keelboat Sailing

    • ASA 103 – Basic Coastal Cruising

    • ASA 104 – Bareboat Cruising

    Learn, relax, and explore—then head home as a certified sailor ready for your next voyage.

  • ASA 101/103 Basic Sailing & Basic Cruising Combo | August 19th – August 21st | Port Washington, WI: $1,357.00

    PORT WASHINGTON, WI
    Prerequisites: None

    ASA101 – This is a perfect course for students with fundamental sailing knowledge. Because of the shortened format, the course moves along quickly. The Basic Keelboat will be a refresher as much as learning new skills. It will provide the necessary knowledge to sail a boat of about 20 feet in light to moderate winds and sea conditions in familiar waters without supervision. The course is taught by USCG Captains and your certification is recognized by the United States Coast Guard as a Safe Boating Course.

    ASA103 – General Description: This course is the next step and serves as an introductory course to the world of coastal cruising. It provides the necessary knowledge to cruise safely in local and regional waters as both skipper and crew on an auxiliary powered sailboat of about 30 – 35 feet in length, in moderate winds and sea conditions.

    Format: This course is offered as a 3 day course over Wednesday, Thursday, and Friday, 8 hours each day.

    Wednesday, August 19th, 2026 (8:30 am – 4:30 pm)
    Thursday, August 20th, 2026 (8:30 am – 4:30 pm)
    Friday, August 21st, 2026 (8:30 am – 4:30 pm)

  • ASA 106 Advanced Coastal Cruising | August 24th – 28th | South Shore Yacht Club, Milwaukee, WI: $3,197.00

    South Shore Yacht Club
    Prerequisites: ASA 104 Bareboat Cruising and ASA 105 Coastal Navigation

    This course equips participants with the essential knowledge and skills to safely operate as the skipper and crew of a sailing vessel ranging from 30 to 50 feet in length. It encompasses both day and nighttime sessions conducted in coastal and inland waters, regardless of weather conditions. Building upon the foundations laid in prior ASA courses, students embark on an extended coastal sail, including overnight passages, where they will learn new concepts and apply advanced sailing techniques and skills.

    The course spans five days and imparts the prequisite expertise for coastal navigation. It instills the confidence to plan, chart, and execute extended coastal cruises under varying conditions on sailboats of up to 50 feet in length.

    Sailing Vessel – 2014 Jeanneau 409 Sun Odyssey
    This is an attractive 40 foot sailing yacht, is designed with 3 cabins and 2 heads. This is a top of the line cruising model with all of the comforts and features to make learning fun and safe. Features include: Roller furling sails, dodger and bimini, anchor windlass, autopilot, GPS, and color chartplotter.

    Note: If you haven’t yet completed your ASA 105 (Coastal Navigation) certification, we recommend enrolling in our online ASA 105 course through Sea Safaris Online. You’ll have the option to complete the final exam during the sailing trip.

  • ASA 101 Keelboat 1 | September 5th & 6th | South Shore Yacht Club, Milwaukee, WI: $597.00

    South Shore Yacht Club
    Prerequisites: None

    Ready to embark on your sailing journey? This course is the perfect starting point for anyone looking to learn the art of sailing. You’ll gain the essential skills and confidence needed to sail a 20-foot boat in light to moderate winds and calm waters without the need for supervision.

    Throughout this comprehensive course, you’ll dive into the fundamentals of keelboat sailing, including:

    • Sail theory and hands-on practice
    • Navigating common sailing terminology
    • Key safety equipment and procedures
    • Crew overboard recovery techniques
    • Mastering essential sailing knots
    • And much more!

    By the end of the course, you’ll be equipped with the knowledge to confidently handle a boat and enjoy time on the water.

    Course Format:
    This course is offered as a 2 day weekend course over Saturday and Sunday.

    • Saturday 8:30am – 2:30pm
    • Sunday 8:30am – 2:30pm
  • ASA 108 Offshore Passage Making | September 21st – 25th | South Shore Yacht Club, Milwaukee, WI: $3,995.00

    South Shore Yacht Club
    Prerequisites: ASA 106 Advanced Coastal Cruising and ASA 107 Celestial Navigation or 117 Celestial Endorsement

    Step up to true offshore sailing with Sea Safaris’ ASA 108 Offshore Passagemaking course, departing from South Shore Yacht Club in Milwaukee. This advanced liveaboard training is designed for experienced sailors who want to confidently plan and execute multi-day, non-stop passages—day and night—well away from the comfort of the marina.

    Over 5 days underway, you’ll stand watches, sail through the night, and experience real offshore decision-making on extended legs across the Great Lakes. You’ll rotate through roles as skipper and watch captain while working with the crew to handle:

    • Passage planning and weather routing

    • Night sailing, lights, and collision avoidance

    • Offshore watch schedules and log-keeping

    • Heavy-weather strategies and sail plans

    • Offshore safety, emergency procedures, and seamanship

    • Power management, provisioning, and boat systems underway

    Our route will be shaped by weather and conditions to ensure at least 72 hours of continuous offshore sailing, meeting the requirements for ASA 108 while giving you genuine passagemaking experience—not just a string of day sails.

    Prerequisites & Certification

    This course is intended for sailors who have already built a solid coastal foundation (ASA 104/106 or equivalent experience). The training is conducted to meet all ASA 108 Offshore Passagemaking standards.

    Sailors who have completed their celestial or electronic navigation study in advance (such as ASA 117 or equivalent) will be especially well prepared to integrate advanced navigation skills into real-world offshore passage planning and execution.

  • ASA 111: Anchoring Skills Clinic | September 26th | South Shore Yacht Club, Milwaukee, WI: $397.00

    South Shore Yacht Club
    Prerequisites: ASA 101 Keelboat Sailing 1

    Master one of the most important cruising skills with this hands-on ASA 111 Sailing Review course focused exclusively on anchoring.

    Whether you’re preparing for a bareboat charter, planning extended cruising adventures, or simply looking to improve your confidence as skipper, this practical clinic will teach you how to anchor safely, confidently, and effectively in a variety of conditions.

    During this course, students will review anchoring equipment and techniques, learn how to select suitable anchorages, evaluate depth, wind, and bottom conditions, calculate proper scope, set and test an anchor, and safely depart an anchorage. Students will also discuss common anchoring challenges, overnight considerations, and strategies for preventing dragging and other anchoring issues.

    Topics include:

    • Types of anchors and ground tackle
    • Selecting a safe anchorage
    • Wind, current, depth, and bottom considerations
    • Calculating and deploying proper scope
    • Setting and verifying anchor holding
    • Anchor watch procedures
    • Retrieving and stowing the anchor
    • Communication and crew coordination
    • Common anchoring mistakes and troubleshooting

    This ASA 111 Sailing Review clinic combines classroom discussion with extensive on-the-water practice to help sailors develop the skills and confidence needed to anchor independently.

    Format: This course is offered as a 1-day course, 9:00 AM – 4:00 PM each day.

    Prerequisites: ASA 101 Keelboat Sailing 1

    Certification: ASA 111 Sailing Review

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