Events
ASA 111: Anchoring Skills Clinic | September 27th | South Shore Yacht Club, Milwaukee, WI: $397.00
South Shore Yacht ClubPrerequisites: ASA 101 Keelboat Sailing 1Master 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
![ASA111, Sailing Skills Review]( "ASA111, Sailing Skills Review")
BVI | CATAMARAN FLOTILLA | FEB 13 – FEB 20, 2027:
Roadtown, Tortolla, BVIPrerequisites:🌴 British Virgin Islands Catamaran Sailing Adventure
February 13–20, 2027❤️ Experience Valentine’s Day on this Trip!
Join us for an unforgettable week sailing through the stunning British Virgin Islands aboard a luxurious 40–44ft catamaran.
Whether you’re looking for the ultimate sailing vacation or want to earn ASA certifications while island hopping through paradise, this adventure combines hands-on sailing, snorkeling, beach bars, waterfront dining, and breathtaking Caribbean scenery.
Our sample itinerary includes stops at:
⛵ Trellis Bay (Beef Island)
⛵ Leverick Bay / Gorda Sound
⛵ Bitter End / North Sound
⛵ Anegada
⛵ Jost Van Dyke
⛵ Norman IslandPricing (double occupancy):
• $2,897 per person — Sailing Vacation Experience
• $3,597 per person — Includes ASA Certification Courses (ASA 101 / 103 / 104 / 114 as applicable)Private queen cabins with ensuite heads included aboard immaculate 40–44ft catamarans.
Spots are limited. Reserve your Caribbean sailing adventure today!
![]( "BVI – Valentines Day week 2-13 – 2-20-2027")
BVI | CATAMARAN FLOTILLA | FEB 20 – FEB 27, 2027:
Roadtown, Tortolla, BVIPrerequisites:🌴 British Virgin Islands Catamaran Sailing Adventure
February 20–27, 2027🌕 Experience the Snow Moon
The last full moon of winter, named for February’s heavy snowfalls. As a bonus, this year’s Snow Moon coincides with a rare penumbral lunar eclipse. Join us in the BVI for this unforgettable week under the stars.
Join us for an unforgettable week sailing through the stunning British Virgin Islands aboard a luxurious 40–44ft catamaran.
Whether you’re looking for the ultimate sailing vacation or want to earn ASA certifications while island hopping through paradise, this adventure combines hands-on sailing, snorkeling, beach bars, waterfront dining, and breathtaking Caribbean scenery.
Our sample itinerary includes stops at:
⛵ Trellis Bay (Beef Island)
⛵ Leverick Bay / Gorda Sound
⛵ Bitter End / North Sound
⛵ Anegada
⛵ Jost Van Dyke
⛵ Norman IslandPricing (double occupancy):
• $2,897 per person — Sailing Vacation Experience
• $3,597 per person — Includes ASA Certification Courses (ASA 101 / 103 / 104 / 114 as applicable)Private queen cabins with ensuite heads included aboard immaculate 40–44ft catamarans.
Spots are limited. Reserve your Caribbean sailing adventure today!
![]( "BVI – Full Moon week 2 – 2-20 – 2-27-2027")
BVI | CATAMARAN FLOTILLA | FEB 27– MAR 06, 2027:
Roadtown, Tortolla, BVIPrerequisites:🌴 British Virgin Islands Catamaran Sailing Adventure
February 27 – March 06, 2027☀️ Week 3 is your Winter Escape! If you can’t make the other dates, this week’s for you! 😎
Join us for an unforgettable week sailing through the stunning British Virgin Islands aboard a luxurious 40–44ft catamaran.
Whether you’re looking for the ultimate sailing vacation or want to earn ASA certifications while island hopping through paradise, this adventure combines hands-on sailing, snorkeling, beach bars, waterfront dining, and breathtaking Caribbean scenery.
Our sample itinerary includes stops at:
⛵ Trellis Bay (Beef Island)
⛵ Leverick Bay / Gorda Sound
⛵ Bitter End / North Sound
⛵ Anegada
⛵ Jost Van Dyke
⛵ Norman IslandPricing (double occupancy):
• $2,897 per person — Sailing Vacation Experience
• $3,597 per person — Includes ASA Certification Courses (ASA 101 / 103 / 104 / 114 as applicable)Private queen cabins with ensuite heads included aboard immaculate 40–44ft catamarans.
Spots are limited. Reserve your Caribbean sailing adventure today!
![]( "BVI – Winter Escape – final – week 3 – 2-27 – 3-6-2027")
ASA 101 Keelboat 1 | May 29th & May 30th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00
South Shore Yacht ClubPrerequisites: NoneReady to become a sailor? ASA 101 Keelboat Sailing 1 is the perfect place to begin. No previous sailing experience is required.
Over one hands-on weekend, you’ll learn the fundamentals of sailing aboard a tiller-steered Hunter 216. With no more than four students per class, everyone receives plenty of time at the helm, trimming sails, practicing maneuvers, and rotating through the different crew positions.
You’ll build a strong foundation in boat handling, sail trim, safety, sailing terminology, crew-overboard recovery, knots, and more, all while gaining the skills and confidence to continue your sailing journey.
Your course includes two full days of hands-on sailing instruction aboard one of our training sailboats, use of all sailing equipment, the official ASA textbook and course materials, plus the ASA 101 examination and certification.
Click the REGISTER button below to view the complete course details, available dates, and tuition, or reserve your place in an upcoming class.
![ASA 101, Basic Keelboat Sailing]( "ASA 101, Basic Keelboat Sailing")
Greece Flotilla – Southern Ionian | CATAMARAN FLOTILLA | JUN 05 – JUN 12, 2027:
Lefkada, GreecePrerequisites:🏛️Greece Flotilla Sailing Adventure
June 5–12, 2027☀️Explore ancient history, charming island villages, and world-class sailing in the heart of the Ionian Sea!
Join us for an unforgettable week sailing through the crystal-clear waters of Greece’s beautiful Southern Ionian Islands.
Departing from Lefkada, you’ll explore charming island villages, secluded bays, breathtaking sea caves, ancient history, incredible Greek cuisine, and some of the finest sailing in the Mediterranean.
Whether you’re looking for the vacation of a lifetime or want to earn ASA certifications while island hopping through Greece, this adventure combines hands-on sailing, crystal-clear swimming, waterfront tavernas, rich culture, and unforgettable scenery.
Our sample itinerary includes stops at:
⛵ Lefkada
⛵ Meganisi Island & Vathi Harbor
⛵ Papanikolis Cave
⛵ Fiskardo (Kefalonia)
⛵ Sami & Melissani Cave
⛵ Bay of Filiatro
⛵ Kalamos & One House Bay
⛵ Vlycho BayPricing (double occupancy):
• $2,897 per person — Sailing Vacation ExperiencePrivate double cabins aboard modern sailing yachts and catamarans.
Spots are limited. Reserve your Greek sailing adventure today!
![]( "Greece – Southern Ionian Islands – 6-5-12-2027")
ASA 101 Keelboat 1 | June 19th & June 20th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00
South Shore Yacht ClubPrerequisites: NoneReady to become a sailor? ASA 101 Keelboat Sailing 1 is the perfect place to begin. No previous sailing experience is required.
Over one hands-on weekend, you’ll learn the fundamentals of sailing aboard a tiller-steered Hunter 216. With no more than four students per class, everyone receives plenty of time at the helm, trimming sails, practicing maneuvers, and rotating through the different crew positions.
You’ll build a strong foundation in boat handling, sail trim, safety, sailing terminology, crew-overboard recovery, knots, and more, all while gaining the skills and confidence to continue your sailing journey.
Your course includes two full days of hands-on sailing instruction aboard one of our training sailboats, use of all sailing equipment, the official ASA textbook and course materials, plus the ASA 101 examination and certification.
Click the REGISTER button below to view the complete course details, available dates, and tuition, or reserve your place in an upcoming class.
![ASA 101, Basic Keelboat Sailing]( "ASA 101, Basic Keelboat Sailing")
ASA 103 Basic Coastal Cruising | June 26th & 27th, 2027 | Port Washington, WI: $897.00
PORT WASHINGTON, WIPrerequisites: ASA 101 Keelboat Sailing 1Ready to move beyond the basics? ASA 103 Coastal Cruising builds on the foundation developed in ASA 101 and introduces you to the skills needed to safely operate a larger, auxiliary-powered cruising sailboat.
During this intensive two-day course, you’ll gain hands-on experience with boat handling under sail and power, docking, sail trim, anchoring, navigation, weather, safety procedures, boat systems, and cruise preparation.
By the end of the course, you’ll have greater confidence handling a cruising sailboat and a solid foundation for planning and enjoying daytime coastal cruises. You’ll also be prepared to continue building your skills with ASA 104: Bareboat Cruising.
Format: This course is offered as an intensive two-day course.
Click the REGISTER button to explore the complete course details, available dates, and tuition, or to reserve your place.
![ASA 103, Basic Coastal Cruising]( "ASA 103, Basic Coastal Cruising")
ASA 101 Keelboat 1 | July 10th & July 11th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00
South Shore Yacht ClubPrerequisites: NoneReady to become a sailor? ASA 101 Keelboat Sailing 1 is the perfect place to begin. No previous sailing experience is required.
Over one hands-on weekend, you’ll learn the fundamentals of sailing aboard a tiller-steered Hunter 216. With no more than four students per class, everyone receives plenty of time at the helm, trimming sails, practicing maneuvers, and rotating through the different crew positions.
You’ll build a strong foundation in boat handling, sail trim, safety, sailing terminology, crew-overboard recovery, knots, and more, all while gaining the skills and confidence to continue your sailing journey.
Your course includes two full days of hands-on sailing instruction aboard one of our training sailboats, use of all sailing equipment, the official ASA textbook and course materials, plus the ASA 101 examination and certification.
Click the REGISTER button below to view the complete course details, available dates, and tuition, or reserve your place in an upcoming class.
![ASA 101, Basic Keelboat Sailing]( "ASA 101, Basic Keelboat Sailing")
ASA 104, Bareboat Chartering | July 17th & July 18th, 2027 | Milwaukee, WI: $1,097.00
South Shore Yacht ClubPrerequisites: ASA101-Keelboat Sailing 1, ASA103-Coastal CruisingASA 104 Bareboat Cruising is a comprehensive cruising course for experienced sailors ready to take on greater responsibility aboard a larger cruising sailboat.
You’ll develop practical skills in basic navigation, cruise planning, provisioning, advanced anchoring techniques, boat systems, maintenance procedures, weather interpretation, and emergency response. You’ll also explore international sailing considerations and learn how to respond to the “what ifs” that might occur when you are away from immediate assistance and become the first responder for your boat and crew.
By the end of the course, you’ll be better prepared to act as skipper or crew aboard a 30- to 45-foot sailboat during a multi-day cruise in inland or coastal waters. Most charter companies require a sailing resume from the skipper and look for an internationally recognized certification such as ASA 104 when evaluating qualifications to charter a boat.ASA 104 also provides a strong foundation for continuing to ASA 105 Coastal Navigation and ASA 106 Advanced Coastal Cruising.
Format: This course is 2 consecutive days with and optional overnight. Students who successfully complete the required written examination and practical skills assessment will earn the ASA 104 certification.
Click the REGISTER button to explore the complete course details, tuition, and to reserve your place in this class.
![ASA 104, Bareboat Chartering]( "ASA 104, Bareboat Chartering")
ASA 103 Basic Coastal Cruising | July 22nd & 23rd, 2027 | Port Washington, WI: $897.00
PORT WASHINGTON, WIPrerequisites: ASA 101 Keelboat Sailing 1Ready to move beyond the basics? ASA 103 Coastal Cruising builds on the foundation developed in ASA 101 and introduces you to the skills needed to safely operate a larger, auxiliary-powered cruising sailboat.
During this intensive two-day course, you’ll gain hands-on experience with boat handling under sail and power, docking, sail trim, anchoring, navigation, weather, safety procedures, boat systems, and cruise preparation.
By the end of the course, you’ll have greater confidence handling a cruising sailboat and a solid foundation for planning and enjoying daytime coastal cruises. You’ll also be prepared to continue building your skills with ASA 104: Bareboat Cruising.
Format: This course is offered as an intensive two-day course.
Click the REGISTER button to explore the complete course details, available dates, and tuition, or to reserve your place.
![ASA 103, Basic Coastal Cruising]( "ASA 103, Basic Coastal Cruising")
ASA 101 Keelboat 1 | August 7th & August 8th, 2027 | South Shore Yacht Club, Milwaukee, WI: $647.00
South Shore Yacht ClubPrerequisites: NoneReady to become a sailor? ASA 101 Keelboat Sailing 1 is the perfect place to begin. No previous sailing experience is required.
Over one hands-on weekend, you’ll learn the fundamentals of sailing aboard a tiller-steered Hunter 216. With no more than four students per class, everyone receives plenty of time at the helm, trimming sails, practicing maneuvers, and rotating through the different crew positions.
You’ll build a strong foundation in boat handling, sail trim, safety, sailing terminology, crew-overboard recovery, knots, and more, all while gaining the skills and confidence to continue your sailing journey.
Your course includes two full days of hands-on sailing instruction aboard one of our training sailboats, use of all sailing equipment, the official ASA textbook and course materials, plus the ASA 101 examination and certification.
Click the REGISTER button below to view the complete course details, available dates, and tuition, or reserve your place in an upcoming class.
![ASA 101, Basic Keelboat Sailing]( "ASA 101, Basic Keelboat Sailing")
