ASA Sailing School

ASA Classes are currently held in Annapolis, MD, Bahamas, Belize, San Diego, and Virgin Islands. We offer courses on all Catamarans and Monohulls in the Waypoints Yacht Charter fleet (except Amajen in Annapolis).

Waypoints Yacht Charters is an ASA-accredited sailing school authorized to offer the internationally recognized keelboat certification courses at each destination. Waypoints Yacht Charters went through rigorous qualification standards and are held to the highest standards in the sailing education world. Our ASA-certified courses allow sailors of all experience levels to become more competent and confident in their abilities.

We provide courses to bring the first-timer to a level of competent seamanship (Basic Seamanship), offer advanced courses for the experienced sailor (Advanced Cruising Standard), and open the world of possibilities for those wishing to charter in the world’s finest sailing destinations (Advanced Ocean Cruising).

Your sailing lesson is taught aboard monohulls and catamarans, complete with the amenities of today’s luxury cruising boats. Our boats provide fully-equipped galleys, air conditioning/generators, private cabins, shared heads (some are private/en-suite), and covered cockpits. No matter which charter destination you choose, you can expect the same level of service and comfort.

ASA Courses Are Available All Summer At
Waypoints Annapolis

Learn to sail this summer on the Chesapeake Bay on the following vessels!

Opportune Moment

2021 Dufor 430 – 3 Cab.

Second Wind

2022 Fontaine Pajot Isla 40

ASA Courses

ASA #101: Basic Keelboat Sailing

This is your first step into the exhilarating world of sailing. This course is designed to teach basic sailing and safety procedures. The covered practices are techniques for handling a keelboat, understanding how to use your sails in the wind to propel the boat, sailing terminology, essential knots, and much more. This includes learning to maneuver the boat while underway. You will practice the skills needed to sail with hands-on sailing experience in light to moderate winds.

  • Identify basic parts of a sailboat and describe their functions
  • Tie and describe the functions of six knots without assistance 
  • Understanding the rules of the road and right of way
  • Learn points of sail 
  • Safety drills, including man-overboard
  • Ability to tie a boat safely to a dock
  • On Water Practical Experience 
  • Learning tacking and gybing maneuvers

2-day course

Includes: Textbook, Log Book, ASA Membership, and Certification Fees. 


ASA #103: Basic Coastal Cruising

Once you have a basic working knowledge of sailing, this is your next step to learn daytime coastal cruising. In this course, you will be putting the skills you learned in the introductory course to practice! You will learn the inner workings of a sailboat’s equipment and systems, how to trim your sails for peak performance, navigation basics, weather analysis and safety, motoring and basic docking skills, boat handling while under power and sail, sailing skills, and hands-on sailing practice. Show the proper purpose and use of safety equipment onboard, fueling, and fire precautions.

  • Practicing proper setting of the sails for various wind conditions and points of sail
  • Identify the main responsibilities of the skipper and crew
  • Display the ability to do a checkout of the vessel’s gear and equipment
  • Ability to describe the actions and precautions to take with reduced visibility
  • Show the proper method of using a personal flotation device in the water and use it safely.
  • Review of the basics of a diesel or gasoline auxiliary engine
  • Steer a compass course under power
  • On the water, practical experience

2-day course

Prerequisites: ASA #101

Includes: Textbook, and Certification Fees.


ASA #104: Bareboat Cruising (Monohull)

This multi-day cruise will be in moderate conditions. Learn how to operate and troubleshoot the engines, electricity, navigational instruments, and other boat systems. Now you will be assuming the position of skipper while learning advanced sailing skills and seamanship, safety at sea, navigation fundamentals, and weather management. You will learn an understanding of liveaboard life, provisioning, and the responsibilities and rewards that come with bareboat cruising.

  • Ability to be on board a live cruise for 48 hours, acting as crew and skipper.
  • Show the method of plotting a course while determining ETA and compass heading.
  • How to troubleshoot and identify various issues with engine malfunction (cleaning strainers, checking fuel filters, etc).
  • Characterize the courtesies and customs of yachtsmen, including the placement of flags, etc.
  • Assessment of safe weather conditions
  • Ability to use and launch a dinghy and outboard engine at anchor.
  • Appropriately prepare for a charter, including provisioning and use of the galley.

2-day course on a monohull.

Includes: Textbook, Log Book, ASA Membership, and Certification Fees.  

Prerequisites: ASA #101 & #103


ASA #114: Cruising Catamaran Sailing

This course will give you hands-on experience on how to skipper a sailing catamaran (a multi-hull vessel). This is a catamaran version of the 104 Bareboat Cruising course.  The auxiliary powered catamaran will be between 40’ and up.. Depending upon your location, you will cruise inland or coastal waters in moderate to heavy winds and sea conditions, following a reefing plan. Maneuvering under power, docking, anchoring and practicing catamaran sailing skills. You will learn to sail fast and safely.

2-day course on a Catamaran.

Includes Textbook, Log Book, ASA Membership, and Certification Fees.

Prerequisites: ASA #101 and #103


ASA #106: Advanced Coastal Cruising Standards

Available on Catamarans and Monohulls.

  • Builds and capitalizes on previous sailing experience to skipper a vessel on extended coastal passages in challenging conditions. Emphasis on decision-making and boat management in variable weather & sea states. 
  • Advanced sail handling and navigation in longer passages
  • Learn heavy weather tactics and emergency procedures
  • Overboard drills and the vessel’s system management and troubleshooting

3-day course

Includes: Textbook and Certification Fees.

Prerequisites: ASA 101 – Keelboat Sailing 1, ASA 103 – Coastal Cruising, ASA 104 – Bareboat Cruising, ASA 105 – Coastal Navigation and demonstrate competencies in all knowledge and skills elements of those Standards.

STUDY MATERIALS: Advanced Cruising & Seamanship (ASA Textbook 106)


ASA Interest Form

Please refer to the ASA Schedule for current dates.

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