What it’s Really Like Learning How to Sail in the Caribbean

For the past few years, I’d been learning how to sail by volunteering as crew onboard a handful of sailboats. While this led to some learning, it also led to a few poor experiences with crazy captains — and a lot of time spent fixing or cleaning boats at anchor. Two captains I’d crewed with had given me fake names — one was a felon on the run.

I’d shuffled through textbooks, watched YouTube tutorials, chartered yachts as a guest, talked to other sailors and still felt like some key element of sailing was missing. Was every crazy captain a misfit from general society? Were the normal ones funded by trust funds or hard crime?

Call it serendipity, but Sailing Virgins had a space for me and my friend Rachel to come onboard in the British Virgin Islands for an intermediate sailing course. Over seven days, we’d hop from island to island, learning everything we’d need to know for our American Sailing Association 101, 103, and 104 certifications. By the end of the week, we’d have the skills to charter a sailboat up to 45 feet in length.

So, how does taking a week-long course compare to years of volunteering as crew? Can you really learn that much in seven days? Here’s what learning how to sail in the Caribbean is really like.

The course was covered by Sailing Virgins. The Salt Sirens covered the cost of flights and travel insurance. All opinions are our own.

Get $100 off any course with Sailing Virgins using the code SALTSIRENS.

Don’t expect a chilled-out charter experience

“Grab the wheel and take us out,” our sailing instructor, Oran, commanded. I looked around. We’d only just gotten onboard. Surely he was talking to one of the more experienced students.

“Go on.”

Nope. He was talking to me. Steering the 10,000 kg sailboat felt like awakening an elephant. Slow, heavy, and consequential if it were to run into something.

Breathe held, I weaved through the narrow (to me) channel and into deep blue. There, all six students took turns steering the sailboat, learning the basics of compass navigation. We motorsailed to our anchorage, arriving in the dark. In just a few hours, I’d picked up skills that hadn’t trickled into my knowledge bank after years of being a passenger on a sailboat. Anchoring at night, steering through tricky passages, soaking in the basics of navigation — all on day one.

The next days were similarly packed with skill learning. On the days we did mooring and docking practices, all six students had at least two to three turns for every skill. That’s 15+ docking and mooring attempts in a day. When you’re just a guest on a sailboat, you might witness or assist with 15 moorings/dockings in two weeks.

When you’re a charter guest, the goal is to relax and soak in the sun. When you’re a sailing student, the goal is to learn. You’ll be spending more sunlight hours out on the water fine-tuning your skills as a sailor than lounging around at a pretty anchorage. But, every time I missed the mooring ball and had to start again, I knew I was one step closer to captaining a sailboat on my own.

Get ready for some incredible blues

You can learn to sail just about anywhere there’s water and wind, but why wouldn’t you want to clock in your sailing hours in the Caribbean? The British Virgin Islands are a paradise for novice sailors. The islands are close enough where you can navigate by line of sight. Once you arrive at your spot for the day, you’re rewarded with white sand beaches and warm, turquoise waters. Your packing list is little more than a handful of swimsuits, a rain jacket, sunscreen, and sandals.

The wind is reliable, the routes are endless, and the sailing community is small enough that you can make friends along the way. A beach bar where you can sip painkillers (rum, coconut milk, orange juice, pineapple juice, and a dash of nutmeg) in the sand is never very far away.

Your crew mates will make or break your experience

There are no strangers in sailing! On a week-long course, you’ll be sleeping, dancing, singing, dining, sailing, drinking, and using the restroom in close quarters. Every personality is undiluted.

Some sailing schools have a traditional approach to teaching, which typically attracts an older audience. According to Sailing Today, the average sailor is 50 years old — many are retired. And while interesting friends and crew mates can be made from all walks of life, there’s no doubt that too large of a lifestyle gap on boats can lead to a mismatch in goals and mannerisms. One person’s explanation is another’s mansplanation!

I was lucky to have crew mates who mostly got along. Before the trip, Rachel and I connected solely through social media — sending each other voice notes and memes over the years. But, our friendship grew infinitely closer once we started sailing together. We’d end the day laughing under the stars (and storm clouds) while trying to fall asleep on deck. Spending 24/7 together, friendships accelerate quicker than they do on land. She, another student from the course, and I have dreams to charter a sailboat someday soon.

Some sailing schools, like Sailing Virgins, cater to social and adventurous sailors who are likely to want to head to the beach for a drink once the day is done. Most of their students are in the 18-40 age range. They also offer alumni weeks and girls only courses for even more tailored experiences.

When I move onto my next certification, I’ll be looking for a course with Sailing Virgins.

You’ll have to overcome your fears

I’m the first one to grab a buoy or a hook once we near a dock. I’m happy to be useful as long as it’s not at the helm. Docking has been a major fear of mine — not only my yacht at risk if something goes wrong, but so are all the other yachts and buildings within its path!

I’d read the book about docking strategies, but it still felt like gibberish to me. It wasn’t until I docked once… twice… three… times that I felt confident to do it on my own someday.

If you think you can skirt around docking, man overboard drills, or commanding crew as ‘captain’ during your sailing course, think again. Some skills are required if you want to pass your American Sailing Association certification. And if you have an instructor as passionate about teaching as mine was, you’ll be doing that skill until you’re quite confident in it.

Your yacht might have a few problems

Talk with old salties long enough and they’ll tell you that yacht life is fixing boats in fine places. This certainly was the case in the Caribbean! Truth be told, I’ve never been on a sailboat that didn’t have some sort of problem.

On the first day, a rope got wrapped around our propeller — which needed to be fixed on day two. Water from our bilge also flowed into my cabin. The boat we buddied with had engine problems and a non-working toilet.

This is obviously incredibly frustrating when you’ve spent a pretty penny chartering a sailboat. But as a student, it’s a realistic learning opportunity. When the boat is rocking and you’re mopping out bilge water in sweltering heat, do you still love sailing? For me, the answer was yes.

How much do you realistically learn?

The ASA 104 course textbook states that at the end of your class, you should “Demonstrate the ability to skipper a sloop-rigged, auxiliary-powered keelboat of approx. 30-45 feet in length during a multi-day cruise upon inland coastal waters in moderate to heavy wind and sea conditions.”

I was very skeptical that I’d walk away with everything I’d need to know to charter a 45-foot sailboat on my own. That would be like writing a book without knowing the letters of the alphabet.

One afternoon, our instructor had us feel the wind and taught us how to take the sailboat on all points of sail. This lesson was one I’d never been taught before, and never fully got through to me in the textbooks. From there, every other element of sailing fell together. I learned more in an afternoon than in weeks of crewing.

With a little more experience, I’m confident I could charter a 45-foot sailboat safely in the near future. I’d trust me, Rachel, and another student to figure out how to manage a boat after our course using everything we’ve learned from Oran.

If you have the budget for it, invest in a proper sailing course before crewing or buying a sailboat of your own. You’ll learn the fundamentals in a fun environment, and won’t pick up bad habits that come with bad captains and self-teaching.

Ready to go? We wholly recommend Sailing Virgins, especially if your course is run by Oran!

Get $100 off any course with Sailing Virgins using the code SALTSIRENS.