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Captains’ Favorites: The ASA Sailing Courses Our Captains Love to Teach

Graphic with a captain's hat, books, and text: 'Captains' Favorites, Favorite ASA course to teach'.Which ASA sailing course is the most fun to teach? We asked our Go Sail Virgin Islands captains, and the answers were surprisingly different!

Some of our American Sailing instructors love the excitement of watching a student sail for the first time. Others enjoy passing along the practical knowledge they’ve gained from years of bareboat chartering. And for one captain, nothing beats heading offshore with an open horizon ahead.

One thing all our captains agreed they love is that every course and every student is unique and each teaching opportunity gives them the chance to help students become more confident, capable sailors.

Whether you’re completely new to sailing, working toward bareboat chartering, or looking to take your sailing farther offshore, the ASA curriculum has courses designed for different stages of your sailing journey. 

Here are our captains’ favorite courses to teach and why.

ASA 101: Watching Someone Become a Sailor

Captain Corey loves teaching sailing fundamentals. 

“ASA 101 is probably my favorite. That first introductory course. How to do everything with the sails. How to put the sails up, how to tack, how to jibe.”

ASA 101, officially known as Basic Keelboat Sailing, introduces students to the fundamentals of sailing. It’s where students begin learning how the boat works, how to control it under sail, and how to communicate with the crew.

But for Corey, the best part isn’t  teaching the skills. It’s watching students start to put everything together.

“I really like seeing that first day when students start getting it. That’s probably where I see the most growth during the week.”

For a sailing instructor, that moment can be pretty rewarding. Students may arrive with little or no sailing experience. By the end of the course, they’re raising sails, steering the boat, tacking, jibing, and beginning to understand how the wind and the boat work together. 

ASA 101 is taught alongside ASA 103, ASA 104, and ASA 114 on Go Sail Virgin Islands sailing vacations. 

ASA 104: Turning Sailing Skills Into Charter-Ready Confidence 

For Julie and Andy, their favorite ASA course to teach is ASA 104.

Their reason has less to do with what’s printed in the textbook and more to do with everything they’ve learned through years of actually chartering sailboats.

“My favorite course to teach is ASA 104 because I get to draw on my lifetime knowledge through the years of bareboat chartering. Tips and tricks the book might not give you.”

That’s an important distinction.

Learning the technical requirements for bareboat chartering is one thing. Learning the little decisions that make a week aboard a sailboat go more smoothly comes from experience.

Those practical lessons are where an experienced instructor can add another dimension to an ASA 104 course.

ASA 104 is the Bareboat Cruising certification and builds on the skills students develop in earlier ASA courses. The focus moves beyond simply learning to sail toward handling a cruising sailboat more independently.

That’s also why Captain JT chooses ASA 104 as his favorite.

“The 104 specifically is the one that really gets people to the next step where they are ready to charter on their own.”

For students who have their sights set on bareboat chartering, ASA 104 can be a particularly exciting milestone. It’s also the course Go Sail Virgin Islands students complete as part of the process for obtaining their International Proficiency Certificate. 

ASA 106: When the Horizon Gets Bigger

Captain Jalil has a very different favorite.

For him, it’s ASA 106, the Advanced Coastal Cruising course.

“My favorite one to do is really the 106 and the reason why is we get to do a couple blue water passages.”

And that gets to the heart of why Jalil fell in love with sailing in the first place.

“Blue water passages is what makes me passionate about sailing in the first place. I know we’re only going 20 miles, but still. It’s nice to have an empty horizon and be out at sea.”

There’s something different about leaving the coastline behind.

The horizon opens up. The scenery changes. The boat becomes your entire world for a while, and you begin paying attention to wind, waves, navigation, weather, sail trim, and the rhythm of the boat.

For experienced sailors, offshore sailing can be one of the most rewarding parts of the sport.

But Jalil knows that the idea of heading offshore can make some students nervous.

His advice is simple:

“A lot of people are intimidated. You don’t have to be scared—it’s just going to be fun.”

That’s one of the advantages of learning advanced sailing skills with an experienced instructor. Students can gradually build the knowledge and confidence needed to take on more challenging conditions while still having an instructor aboard.

Learn to Sail in the Virgin Islands

At Go Sail Virgin Islands, our captains don’t just teach sailing because it’s their job. They teach because they love being on the water and they love seeing students become more confident sailors.

For Corey, that’s watching the lightbulb come on during ASA 101.

For Julie and Andy, it’s sharing the practical knowledge they’ve gained through years of bareboat chartering during ASA 104.

For JT, it’s helping students reach the point where they’re ready to charter independently.

And for Jalil, it’s the feeling of sailing toward an empty horizon.

There isn’t just one way to love sailing.

That’s why there isn’t just one favorite ASA course.

Ready to find your next sailing milestone? Explore Go Sail Virgin Islands ASA sailing courses and learn to sail in the Caribbean with experienced instructors who love sharing what they know.