Learn To Sail With Waypoints
Earn an internationally recognized ASA certification — aboard a luxury yacht, at a destination worth sailing to.
Waypoints Yacht Charters is an ASA-accredited sailing school, authorized to offer internationally recognized keelboat certification courses across multiple destinations. Our courses are taught aboard the same luxury monohulls and catamarans that make up our charter fleet — fully equipped galleys, air conditioning, private cabins, covered cockpits, and every comfort of a proper cruising yacht. The classroom is the boat. The curriculum is the sea.
ASA courses are currently available at Waypoints Annapolis (Chesapeake Bay), and through our partners in the Bahamas, Belize, San Diego, CA and the U.S. Virgin Islands. All courses are offered as private instruction on vessels ranging from 37 to 53 feet, meaning your course is tailored to your group rather than shared with strangers.
Waypoints went through rigorous qualification standards to earn ASA accreditation and is held to the highest standards in sailing education. Our certified instructors bring that standard to every course, at every destination, at every level of experience.
Why
Learn With Waypoints?
At Waypoints, every course is private, taught on a luxury yacht from our fleet, and structured around your group’s pace and objectives. Non-sailing guests traveling with a student are welcome aboard — our instructors are experienced at integrating lessons into a genuinely enjoyable charter experience for everyone.
When the course is done, you leave with an ASA certification that is recognized by bareboat charter companies around the world — the credential that opens up independent sailing at every Waypoints destination and beyond.
The ASA Certification Pathway
ASA certifications progress through a structured pathway from complete beginner to offshore passage-making skipper. You can join at any level and advance as far as your goals take you. Below is the full range of courses Waypoints offers.
LEVEL 1 — Basic Seamanship
ASA 101: Basic Keelboat Sailing
2-day course | No prerequisites
The entry point for every sailor. ASA 101 covers the fundamentals of sailing and safety in light to moderate winds — everything you need to handle a keelboat confidently from day one. By the end of the course, you’ll know the boat, the terminology, the rules of the road, and the core maneuvers that underpin all sailing.
Includes: Textbook, Log Book, ASA Membership, and Certification Fees.
What You'll Learn
- Parts of a sailboat and their functions
- Six essential knots and their uses
- Rules of the road and right of way
- Points of sail and how to use the wind
- Safety drills, including man-overboard procedures
- Tacking and gybing maneuvers
- How to dock safely
ASA 103: Basic Coastal Cruising
2-day course | Prerequisite: ASA 101
The natural next step after Basic Keelboat. ASA 103 moves from fundamental skills to daytime coastal cruising — sail trim, navigation basics, weather analysis, motoring and docking, and a deeper understanding of the boat’s systems and equipment. This is where sailing starts to feel like something you own rather than something you’re learning.
Includes: Textbook and Certification Fees.
What You'll Learn
- Sail trimming for various wind conditions and points of sail
- Skipper and crew responsibilities
- Vessel gear and equipment checkout
- Navigation basics and compass work under power
- Weather awareness and reduced-visibility procedures
- Safety equipment use and fire precautions
- Diesel and gasoline auxiliary engine basics
LEVEL 2 — Advanced Cruising Standard
ASA 104: Bareboat Cruising (Monohull)
2-day live-aboard course | Prerequisites: ASA 101 & 103
ASA 104 is the certification that unlocks independent bareboat chartering at destinations worldwide — including all Waypoints bases. This multi-day cruise puts you in the skipper’s seat: operating and troubleshooting the boat’s systems, advanced sailing and seamanship, navigation, weather management, and the full experience of liveaboard life including provisioning and galley management.
Includes: Textbook, Log Book, ASA Membership, and Certification Fees.
What You'll Learn
- Live 48 hours aboard as crew and skipper
- Course plotting with ETA and compass heading
- Engine troubleshooting and maintenance (fuel filters, strainers, and more)
- Safe weather assessment
- Dinghy and outboard operation at anchor
- Provisioning and galley preparation
- Yachting customs and etiquette
ASA 114: Cruising Catamaran Sailing
2-day course on a catamaran | Prerequisites: ASA 101 & 103
The catamaran equivalent of ASA 104 — covering everything you need to skipper a sailing catamaran of 40 feet and above. Inland or coastal waters, moderate to heavy conditions, maneuvering under power, docking, anchoring, and the specific handling characteristics that make catamarans both rewarding and distinct from monohull sailing.
Includes: Textbook, Log Book, ASA Membership, and Certification Fees.
What You'll Learn
- Live 48 hours aboard as crew and skipper
- Course plotting with ETA and compass heading
- Engine troubleshooting and maintenance (fuel filters, strainers, and more)
- Safe weather assessment
- Dinghy and outboard operation at anchor
- Provisioning and galley preparation
- Yachting customs and etiquette
LEVEL 3 — ADVANCED COASTAL CRUISING
ASA 106: Advanced Coastal Cruising
3-day course | Available on catamarans and monohulls Prerequisites: ASA 101, 103, 104, and 105
For experienced sailors ready to take on extended coastal passages in challenging conditions. ASA 106 focuses on decision-making and boat management in variable weather and sea states — the skills that separate a competent sailor from a confident one.
Includes: Textbook and Certification Fees.
Study materials: Advanced Cruising & Seamanship (ASA Textbook 106)
What You'll Learn
- Advanced sail handling and navigation on longer passages
- Heavy weather tactics and emergency procedures
- Man-overboard drills and recovery
- Vessel systems management and troubleshooting
Frequently Asked Questions
Where Can I Take A Course?
ASA courses through Waypoints are currently available at the following locations:
Waypoints Annapolis — Chesapeake Bay, Maryland Summer courses on the Chesapeake Bay aboard vessels including the 2021 Dufour 430, 2018 Sun Odyssey 389, and 2022 Fountaine Pajot Isla 40. All summer availability.
Waypoints Bahamas Courses available through our Cruise Abaco partnership in the Sea of Abaco.
Waypoints Belize Courses available through our Belize Sailing Vacations partnership.
Waypoints USVI Courses available from our Frenchtown Marina base in St. Thomas.
Waypoints San Diego Courses available through our partnership with Seaforth Yacht Charters.
Courses are also available through our Newport, Rhode Island partner New England Sailing Center — including an expanded range of advanced and offshore certifications. Contact a Waypoints Yacht Charters Specialist for details.
Do I need any sailing experience to start?
No. ASA 101 is designed for complete beginners and requires no prior sailing experience. If you already have some time on the water, your Waypoints Yacht Charters Specialist can help you identify the right entry point in the certification pathway.
Can non-sailing guests come aboard during a course?
Yes. Our instructors are experienced at integrating ASA coursework into a charter that is enjoyable for everyone — students and non-students alike. Families and couples who want to learn at different levels or at different paces are all accommodated.
What boats are used for instruction?
All courses are taught aboard vessels from the Waypoints charter fleet — luxury monohulls and catamarans ranging from 37 to 53 feet, with full galley, air conditioning, private cabins, and covered cockpits. The same boats you’d charter for a sailing vacation.
How long does it take to become certified to bareboat charter independently?
ASA 101 and 103 together cover the fundamentals in four days. Adding ASA 104 (Bareboat Cruising) gets you to the certification level recognized by most bareboat charter companies worldwide. The full pathway from beginner to independent bareboat skipper can be completed in as little as a week — which is why our Bahamas and Caribbean destinations are popular choices for combining certification with a genuine sailing vacation.
Are ASA certifications recognized internationally?
Yes. ASA certifications carry international recognition and are accepted by bareboat charter operators around the world, including at all Waypoints destinations.
How do I register?
Complete the interest form to connect with a Waypoints Yacht Charters Specialist. We’ll confirm course availability at your preferred destination, match you with the right course level, and handle the booking from there.