A Learn to Sail Caribbean Vacation: Rookie to ASA Sailor in 7 Days

Learn to Sail Vacation Caribbean

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Inside: Planning a “learn to sail vacation” to get your ASA sailing certification? From the best Caribbean sailing schools to what a week long course is actually like, here’s every little thing you need to know.

When pressed, I cannot offer a reasonable explanation as to why my husband, Dave, and I suddenly decided we must learn how to sail.

It sounds fun? Well, sure. But so does a spa holiday.

Sailing holidays are glamorous? Obviously! (But, as it turns out, sailing classes are decidedly not.)

We’re in the market for a powerboat? Nope, that would be a good reason to take a powerboat course.

Dave and I are indeed in the market for a boat. Ideally, a roomy powerboat to moor in Seattle’s Puget Sound area (his hometown). A floating condo, if you will, to use as a home base for our regular visits.

So, I suppose there’s just one reason learning how to sail seems like a good idea. We want to be educated buyers when we purchase our boat. Is it possible that a sailboat might be a good option for us?

How will we know unless we try it?

Why not learn how to sail in the Caribbean?

If learning how to sail sounds like fun, then surely learning how to sail in the Caribbean would be even better!

I’ve only been sailing once before. A few blissful days aboard Kokomo, a 36′ monohull, in Panama’s remote San Blas Islands.

Read More: Kokomo, Kuanidup & the Kuna Yala: The San Blas Islands, Panama

After that trip, I was definitely inspired by the sailing lifestyle. But you don’t just decide to become a sailor.

No, that would be too easy.

Learning to sail involves intense studying and many skills to master. Surely it takes months, even years…right?

Not necessarily. But more on that in a moment.

The next step, finding a sailing school!

How to choose the best Caribbean sailing school

As luck would have it, the Caribbean has several wonderful sailing schools. From the British Virgin Islands to the Grenadines, there’s a Caribbean sailing school to suit every salty sailor from rookies (like us) to experienced sailors looking to expand their knowledge.

Most Caribbean sailing schools offer everything from basic sailing courses to intense liveaboard multi-course options at a wide range of prices.

This brings me to the Barefoot Offshore Sailing School (BOSS).

Barefoot Offshore Sailing School St Vincent
Barefoot Offshore Sailing School, St Vincent & the Grenadines

Before settling on Barefoot, we carefully researched half a dozen sailing schools scattered across the Caribbean. Most are based in the Virgin Islands and pretty expensive (approximately $3-4k per person for a week-long course).

While learning how to sail is important to us, $6,000-$8,000 for a week in the Caribbean seems a little steep. When we find Barefoot, however, we discover that the school has all of the same great reviews as the other schools – for nearly half the price.

And we have a winner!

Our ASA Sailing Course Learning Plan

Barefoot offers a number of American Sailing Association (ASA) liveaboard courses.

Being the overachievers that we are, we opt for the most ambitious. It’s a 7-day, 6-night adventure with the opportunity to complete four ASA courses:

  1. ASA 101 – Basic Keelboat
  2. ASA 103 – Basic Coastal Cruising
  3. ASA 104 – Bareboat Cruising Made Easy (you must complete this course to charter a sailboat)
  4. ASA 114 – Catamaran Cruising (specific to catamarans and powerboats – the types of boats we actually plan to buy)

Note: Because I know it’s bugging you, as it did me: there is no ASA 102 course, it’s an older course that was retired.

The most popular week-long course covers just 101 to 104. But we decide adding the catamaran course will be beneficial for additional practice with powerboats. Plus, it will give us more options if we decide to attempt a holiday sailing charter someday.

Now, most experienced sailors will tell you that a monohull is the only true way to experience sailing in its purest form. And that’s probably true. However, catamarans can be far more comfortable from a stability and living space standpoint than a monohull sailboat.

And I’m just going to say it. Dave and I are built for comfort. Not a 25-degree heel while underway.

What are the best months to sail the Caribbean?

Obviously, when planning a sailing course in the Caribbean, you’ll want to avoid the Atlantic hurricane season months of June 1st to November 30th.

The best sailing conditions in the Caribbean are from December to April. During these months, you’ll have the best chance for sunny skies and calm seas. Though, as we later discover, calm seas are no guarantee!

We chose the month of February for our Caribbean “learn to sail” vacation.

Learn to Sail Vacation Caribbean ASA Sailing Courses
There’s no better place than the Caribbean to learn to sail!

Learning How to Sail: The Homework

But it’s not long before we realize that this Caribbean vacation won’t be like any of our previous tropical holidays.

This one comes with homework…and lots of it!

We book our February course in September and immediately get online to order the textbooks for ASA 101, ASA 103, ASA 104 and ASA 114.

When they arrive, they are alarmingly thick.

We have the best intentions to begin studying immediately. Truly, we do.

We’ll be totally prepared! We will read these books cover to cover! We’ll quiz each other on nautical terms and practice tying knots!

We’ll be the best students they’ve ever seen!

We will…

Forget where the heck we put those books until 3 months later. Give or take.

Time for a reality check

As the holidays roll around, we dust off the ole’ “learning to sail” ASA textbooks and smugly begin reading the first book. We still have two months to prepare. Easy peasy!

But the ASA 101 book is like learning another language.


We quickly realize that four courses in one week for two people who have NEVER sailed is ridiculously ambitious. Barefoot recommends that new sailors take every opportunity to get out on the water before they arrive in the Caribbean for their live-aboard sailing course.

We need to find a way to get out on the water STAT. And maybe even knock out ASA 101 somewhere before we go. Just to take some pressure off the whole experience.

Enter, ASA 101 in sunny San Diego…

As the end of the year approaches we also realize we need some miles in our Delta accounts. Why take a sailing course on a freezing cold lake in Atlanta when you can fly to San Diego and do it there?

So obviously, that’s what we do! (Honestly, it’s a no-brainer.)

We find a school called Harbor Sailboats in San Diego and sign up for a weekend ASA 101 course. It turns out to be a wonderful two days of sailing time in the San Diego Bay with a reasonable amount of classroom time thrown in for good measure.

The additional experience proves invaluable to our success two months later.

The ASA 101 written test is 100 questions and it is no joke! We’re thankful that we studied as much as we did.

With the first course out of the way, our new love for sailing is blossoming. We’re feeling a lot better about our chances in St. Vincent and looking forward to expanding our sailing knowledge on a bigger sailboat in turquoise Caribbean seas.

Next stop, the Caribbean!

Located between St. Lucia and Grenada in the southern Caribbean Sea, the multi-island nation of St. Vincent & the Grenadines (SVG) is comprised of 32 islands and cays spanning 45 miles.

Of those 32 islands, only 8 are populated.

Sailing St Vincent Grenadines
The Tobago Cays, St Vincent and the Grenadines

The Grenadines may be one of the Caribbean’s best kept secrets for sailors (ok, to be honest, they’re no secret these days!). Most charter holiday seekers flock to the US and the British Virgin Islands for their turquoise waters and closely-grouped abundance of picture-perfect islands.

But the Grenadines offer all the same beauty at a more affordable price.

St. Vincent & the Grenadines

The largest of the islands is St. Vincent. Home to the majority of SVG’s population of 110,000, it’s also the home base for the island’s booming yacht charter industry.

Popular destinations for sailors include the islands of Bequia, Union, Cannouan, the Tobago Cays, and Mayreau. The Grenadines are also well-known for a handful of exclusive private island resorts on Mustique, Petit St. Vincent, and the luxe Palm Island Resort.

But there will be no private island resorts for us on this trip. We are staring down the barrel of a child-sized cabin for two, a limited water supply, and a hand-pump toilet.

Sorry…ahem, I mean, a glamorous, Caribbean sailing holiday!

Arrival in St. Vincent

After a quick 20-minute flight from St. Lucia (where we spent a few days on the way), we are welcomed at St. Vincent’s gleaming new airport. It seems decades ahead of the one we just left behind in Castries.

Read More: Giving St. Lucia a Second Chance

We breeze through Immigration and Customs and our driver (sent by the Barefoot Sailing School) is waiting for us as we exit baggage claim.

For our first two nights on the island, we will stay at the Barefoot Suites, the company’s small hotel above the charter base. It’s nothing fancy but our room does have a lovely view over the picturesque Blue Lagoon. And it’s the perfect place to observe the boats coming and going from the Barefoot dock each day.

Barefoot Suites View St Vincent
The view from our terrace at the Barefoot Suites

As we engage in some vigorous last-minute studying from our terrace, we watch the monohulls and cats come and go from the docks.

We see many of Barefoot’s fleet arrive back after a week at sea. Some carrying charter guests and others, presumably, sailing students.

Some people getting off the boats appear freshly showered, relaxed, tanned, and well-dressed. While others are somewhat bedraggled and alarmingly grateful to be back on dry land.

Later, with the benefit of hindsight, I realize the clean, refreshed sailors were likely charter guests. While those looking like they were just rescued by the Coast Guard were almost definitely sailing students.

Learning How to Sail, Day 1 – St. Vincent to Bequia

The next morning, we arrive at the restaurant eager to meet our instructor and fellow students. We are full of nervous energy for the week to come.

Have we studied enough? Will we be seasick? Can we actually pass all of these ASA courses in a week? Will there be a hairdryer? (Spoiler alert, no.)

We first meet our instructor, Canadian-based Captain Joel.

Our fellow students for the week are Nick and Alyssa, a lovely couple from London, also totally new to sailing.

During the course of the week, Alyssa reveals that Nick actually booked the trip and later presented her with textbooks for her upcoming “Caribbean sailing holiday.” Alyssa is a much better sport than I probably would have been in her shoes. She also turns out to be a keen student. As does Nick.

First up, the ASA 101 test

The first order of business before departing the charter base is to take the ASA 101 written exam.

BAM! A test, right out of the gate.

At this point, Dave and I are incredibly grateful that we’ve already passed this test. We sit comfortably by while our new friends from London ace it pretty quickly (they have clearly done the advanced studying!).

Learning to Sail Caribbean
Our home for the next 7 days, Isaphil!


We are next introduced to our home for the next 7 days, Isaphil – a 38’ Lagoon catamaran with 3 cabins and 1½ heads (that’s boat talk for bathrooms).

I’m pleased to discover Isaphil is surprisingly roomy. Most of her modern conveniences are powered by batteries and twin diesel engines. No air conditioning, of course, but with small fans in the cabins and the hatches left open, the Caribbean breezes will suffice.

We load our provisions for the week (selected online in advance) and unpack our small bags in our cabins.

Then, it’s time to prepare for departure.

Slipping the lines…here goes nothing

Our first sail is relatively short.

From Blue Lagoon, St Vincent we cross the Bequia Channel to the island of Bequia (pronounced bek-way), the sail takes just two and a half hours.

The first sail is terrific. Dave and I are easily able to adapt the basic sailing skills we learned in San Diego, like tacking and jibing, to the larger catamaran.

Dave is truly in his element and I start to believe that learning to sail might actually be fun! Especially as we cruise into our first picturesque anchorage in Bequia just before sunset.

Sailing Lessons Caribbean Sunset
Catamaran sunset views

Anchoring 101

We make our way to Joel’s favorite anchorage spot (which he indicated earlier on a map) and begin our first attempt at anchoring.

It is somewhat of a disaster.

I’m still not sure exactly why. Too many boats nearby? Not enough swing room (another fancy nautical term)? Too many rookie sailors trying to be helpful?

Who can say?

Most likely, a combination of all of the above. We try several times unsuccessfully before Joel finally suggests we give up and rent a nearby mooring ball for the night.

Anchoring 101 Mooring Ball 101

To top it off, we manage to fumble the boat hook into the drink while trying to pick up the mooring ball. It is not a stellar first effort and I have no doubt Joel is now wondering what he’s in for this week.

In other news, we need a new boat hook.

3 Cheers for Anchor Beers, the best part of a sailing holiday

Eventually, Joel is able to secure us to the mooring ball and we all experience a new favorite ritual…anchor beers!

Since this is a sailing class, not a sailing vacation, no drinking is allowed during the day while we’re underway.

However, the dropping of the anchor each evening signifies it’s time to sit back, enjoy the sunset and crack open the adult beverage of your choice.

Unfortunately, by now the sunset has long since passed.

Silver lining? The anchor beers are extra cold.

By now, we are too tired to pile in the dinghy and head ashore for dinner. So we utilize our on-board provisions and combined brainpower to throw together a surprisingly tasty pasta for dinner.

Learning How to Sail, Day 2 – Bequia to Mayreau

The next morning, we are up with the sun (as we will be every day) to head ashore and see some of Bequia.

We also need to shop for a few more things – for example, a new boat hook – before departure.

Learning How to Sail Bequia Grenadines
Shopping for provisions in Bequia

Bequia is a cute little town. We pick up ice, a few additional provisions, and more adult beverages at the market. Because, after last night, all indications are pointing to the need for increased amounts of adult beverages to survive this week!

Suitably provisioned, we stop by the lone marine store for the boat hook. Then we stroll Bequia’s quaint, colorful waterfront for a bit before returning to Isaphil.

Plotting a course & readying the boat

Today is the longest of our sailing days, five hours at sea from Bequia to Mayreau.

We begin with navigation and Joel teaches us how to plan out our departure, sailing course, and arrival at the next anchorage.

I won’t bore you with the details but let’s just say this part of learning how to sail is far more difficult than I imagined. It involves navigational charts, weather forecasts, tide charts, and more math than the average adult without a smartphone is likely comfortable with.

Satisfied that we have a good course planned out, we begin our pre-departure checks.

Engine checks, bilge pump checks, PFD’s (personal flotation devices) on, sunscreen on, hats, gloves. There is an entire routine to be completed prior to raising the anchor each day.

Wait, maybe this will be a sailing vacation!

By 10:00am we are finally underway and it is a beautiful Caribbean day despite rough seas.

The highlight of the day is meeting up with a pod of dolphins who swim playfully alongside us for nearly half an hour. It is one of the few moments of the week we all actually feel like we are on vacation.

Learning How to Sail Caribbean Dolphins
Why you learn to sail in the Caribbean!

In fact, Joel even takes the helm and orders us all up to the bow to go “be on vacation and play with the dolphins” for a bit.

Nope, maybe not.

But unfortunately the fun doesn’t last.

The sail starts out fine but after an hour or two of rough seas and 40-knot winds, none of us (except Joel and Dave) are feeling great.

But I am definitely feeling the worst of the bunch. In fact, by hour two at sea, I’m feeling downright lousy.

I am the designated navigator for the first part of the day which means continually going into the salon to track our progress on the chart. Every time I go below deck I feel worse. And by the middle of the day, I am miserable.

Seasickness sucks

I haven’t been seasick since I was a kid. And, to be honest, I thought I was invincible.

Boy, was I wrong.

Not too long ago I cruised through the Drake Passage (considered the world’s roughest sea crossing) twice going to and from Antarctica. I spent most of the voyage with a glass of champagne in one hand while pointing out whales with the other and never broke a sweat.

Read More: Expedition Antarctica: Why it’s Worth Every Penny

But this 5-hour crossing between Caribbean islands really does me in.

Sitting on the deck and staring at the horizon (which usually works) doesn’t help at all. Eventually, I end up down in our cabin in bed for an hour or two, which ironically does help tremendously.

By the time we arrive in Mayreau I am feeling almost human again.

Learning How to Sail Catamaran Sunset Mayreau Grenadines
Anchor beers and sunset, a winning combination!

Anchored, at last

We successfully anchor for the first time, hooray! And it’s just in time to watch a marvelous sunset.

Anchor beers for everyone!

Since the restaurant options are limited at our anchorage, Joel suggests we grill chicken (included with our provisions) for dinner. After a very long day, we all agree.

After dinner, Joel has another theory lesson for us (a nightly routine). Eventually, we all fall into bed completely spent by 9:30pm.

Caribbean Sailing Course, Day 3 – Mayreau to Tobago Cays

On our third day of sailing lessons, we awake to a gorgeous rainbow. After yesterday’s queasiness, I’m relieved that today’s sail is a short one, just 2-3 hours.

Learning How to Sail Caribbean
Hopefully a sign for calmer waters today

Today, our course is set for the most popular hot spot in the Grenadines, the Tobago Cays.

Sailing the Incredible Tobago Cays

The Tobago Cays are five tiny islets famed for their white sand beaches and spectacular coral reef.

These uninhabited islands comprise a national park and are incredibly popular with sailors. The plan for the day is to get the coursework and sailing lessons out of the way early. Then, we can enjoy some quality time snorkeling when we arrive in the spectacular Tobago Cays.

Learn to Sail Caribbean Tobago Cays
The Tobago Cays, Grenadines

The other big activity in the Tobago Cays is the nightly lobster BBQ held on shore.

Several local entrepreneurs have developed quite an operation where they catch fresh fish and lobster in the surrounding waters and grill it up ashore each night for the dozens of sailboats anchored nearby.

Joel mentioned the lobster BBQ to us last night so we’re all excited for a lobster dinner on the island tonight. It’ll be nice to have a night off from the cramped onboard galley.

He calls ahead to his favorite fisherman, Captain Neil, and makes a reservation for the 5 of us. When we arrive that afternoon Captain Neil even brings by the day’s catch for our approval (and for a photo op).

Caribbean Lobster Sail Course Grenadines
Now THAT is a lobster! Thank you Captain Neil!

The sail is better this time. Short enough that no one suffers too much discomfort, despite the rough seas. We arrive at our anchorage around 3:00pm and drop anchor.

There is plenty of time left for snorkeling. Unfortunately, a rain shower blows through just as we crack open our anchor beers.

A lobster BBQ ashore in the Tobago Cays

As the sun sets, we board the dinghy and head ashore to join about 50 other cruisers for dinner.

It’s quite a set-up. Picnic tables line the beach with bistro lights strung overhead and amazing smells waft up from the BBQ huts nearby. It is cruiser heaven.

Rum punches are served all-around and the atmosphere is festive as we await our scrumptious crustaceans.

Lobster BBQ Tobago Cays Caribbean
The set-up for the nightly lobster BBQ in the Tobago Cays

We are joined at our table by the crew of a fellow Barefoot sailboat with an instructor and two students aboard.

Before we know it, the most incredible trays of lobster, seafood, and side dishes are placed before us. It is quite possibly the largest lobster I have ever had in my life and it is delectable!

Caribbean Lobster Tobago Cays Grenadines
Lobster dinner, Caribbean style!

The entire meal is wonderful and it is probably our favorite night of the entire trip. For an hour or two, it’s a welcome break from the coursework and truly feels like a vacation!

Becoming a Sailor, Day 4 – Tobago Cays to Union Island (Valentine’s Day!)

Day four starts early with a little bit of vacation time squeezed in before we move on to the business of the day.

Since we are anchored in the gorgeous Tobago Cays, it’s time to go for a snorkel and see some turtles!

Tobago Cays Grenadines
Dinghy ashore in the Tobago Cays

And also to take a little hike on the island to see the iguanas.

We pile into the dinghy with our snorkel gear and motor over to the roped-off swimming area. There, we tie off the dinghy and dive in in search of turtles.

Tobago Cays St Vincent Grenadines
Hiking on the island

The water is rough (as it has been all week) and the current is strong. Dave and I don’t last long before swimming to shore to enjoy the beach. Nick, Alyssa, and Joel persist and are rewarded with a few turtle sightings.

After swimming a bit longer, everyone reconvenes on the beach to hike up the hill and see the iguanas and the island’s scenic viewpoints.

Iguana Tobago Cays Sailing Grenadines
Iguana in the Tobago Cays

The view of the islands in the sparkling turquoise Caribbean Sea is truly incredible. It even reminds me of some of my favorite South Pacific spots (minus the overwater bungalows!).

Read More: Forget Bora Bora: 3 Reasons Moorea is the Best of Tahiti

I just wish we had more time to enjoy it. But it’s time to head back to the boat, get cleaned up, and begin sailing school for the day.

Before we depart, Captian Neil stops by to drop off a tuna he caught for us that morning (at Joel’s request). He slices it up into steaks and we store it in the fridge to save for dinner tomorrow night.

Sailing to Union Island

Today, our destination is the anchorage of Clifton on Union Island.

Like most days, we have two to three hours of sailing ahead. And like most days, the winds are strong and the seas are rolling. Nothing left unsecured on a shelf in the cabins below is safe.

For this stop, Joel has a trick up his sleeve.

We are in need of a refill on our freshwater tanks. Joel knows that if you are the last customer of the day on Lambi’s water dock in Clifton you can moor there overnight free of charge if you eat at their restaurant.

Union Island St Vincent Grenadines
Arriving on Union Island

Since the restaurant has a steel drum band and it’s Valentine’s Day, that sounds like a great plan to all of us.

Not to mention the luxury of being tied up to a dock overnight and simply stepping on and off the boat at our leisure. The daily dinghy transfer is gradually losing its novelty. Plus, the additional boat stability provided by dock versus anchor will be a welcome change.

After another rough sail and a few new skills tests, we arrive in Clifton at 2:00pm. It’s still too early to hit the water dock and be the last customer. So we find a suitable temporary anchorage and head into town to explore.

The town of Clifton

The town of Clifton is my favorite of the islands we visit.

The streets are lined with pastel-colored shops, cafes and vegetable stands. We wander for a bit before settling in at Joel’s recommended stop – the Snack Shack – for ice cream and wifi.

Clifton Union Island Grenadines
The cute little town of Clifton

At 4:00pm we head back to the boat and cruise up to the water dock just before closing at 5:00pm. We are indeed the last customer of the day, so we tie off our mooring lines and then Joel squeezes in one more theory lesson before dinner.

A romantic Valentine’s Day dinner at Lambi’s is thoroughly enjoyed by two happy couples plus one Joel (sorry, Joel!).

Lambis Union Island Grenadines
Isaphil docked at Lambi’s for Valentine’s Day

Learning to Sail, Day 5 – Union Island to Cannouan

The next morning, at Joel’s urging, we all feel ready to take on the ASA 103 written test before setting sail for Cannouan.

Since today’s sail is another short one (just 2 ½ hours) we have a little extra time to spare in Clifton. So, for the only time all week, we sleep in slightly past 7:00am.

Oh, the luxury!

By 11:00am, we have all successfully passed the 103 written test and are feeling a little more confident. We might make it through this week after all!

Clifton Union Island St Vincent Grenadines
The white sands of Clifton, Union Island

Today’s sail begins our journey back toward St. Vincent.

Joel decides to break up the return voyage with an overnight stop in Cannouan. This way we won’t have another 5-hour sailing day to endure (bless you, Joel).

The sail to Cannouan is rough but not nearly as bad as Day 2. However, the toughest part of the day is still ahead, man overboard drills.

Man Overboard! (thankfully, not really)

Joel saves the fun of man-overboard drills until we arrive in the calmer waters of our anchorage at Cannouan.

While arguably the most important skill we will master during our week at sea (this one is, after all, life or death), this technique proves to be a challenge for everyone.

We are tested first on picking up a man-overboard under power. For our skills test, the man overboard in question is portrayed by a life vest tied to two fenders we nickname Carl.

We grow to hate Carl. And I’m pretty sure he knew it based on the number of times we ran him over.

After a couple of tries, we all manage to successfully maneuver the boat into position to rescue Carl without coaching from Joel. Power test passed!

Next, Joel has us attempt the same skill under sail. The maneuver under sail is quite a bit more intricate. We all struggle with it but each manage to execute the maneuver at least once. (I choose not to dwell on how many times we may have executed Carl in the process).

Skills test complete, we head into the anchorage and pick up a mooring ball for the night.

Anchor beers for all!

None for Carl.

But enough about Carl

That night we cook dinner on board, grilling up the delicious tuna caught by Captain Neil yesterday. It is wonderful and we are, again, exhausted.  

Greandines Sailing Caribbean
Captain Neil slicing up our fresh tuna steaks yesterday

I honestly don’t think any of us stay up past 9:00pm on any night of this trip. More often, we are out cold not long after sundown.

Caribbean Sailing Course, Day 6 – Cannouan to Bequia

Our final full day at sea begins like all the others – breakfast cooking, breakfast cleaning, engine checks, bilge checks, PFD’s, sunscreen, gloves, etc.

By this point, it is becoming a familiar routine and we are all in sync and rotating responsibilities with seamless efficiency.

We knock out the morning routine quickly and set about charting our course for the day. We’re headed back to our first stop, Bequia, taking turns being skipper along the way.

Due to strong headwinds, we motor-sail most of the way (a combination of using the sails while also running the engines on low RPMs to increase our speed). We take turns successfully completing our skipper duties and I’m up last.

Engine failure…

A few minutes into my skipper reign, I am drunk with power and have just ordered up a “round of cookies for everyone!” from my first mate, Joel. But just as I’m settling into a groove, the port engine sputters and takes its last breath.

Figures this would happen on my watch.

Thanks to the sails and the starboard engine we are still underway and progressing nicely. But the lack of an engine will impact our ability to maneuver once we reach our anchorage.

Since we don’t need the engines for the final testing of our man overboard drills under sail, we are still able to complete that testing once we reach the calmer waters of Bequia.

It takes everyone several tries (and Carl takes a beating) but eventually, we all manage to rescue Carl under sail without any instruction from Joel.

Bequia St Vincent Grenadines
Back in Bequia

No engine, no problem

Once we complete our final skills test, Joel takes over the helm as we approach Bequia on a single engine. Instead of heading for the popular anchorage near town, he continues down the coast where there are fewer boats and we’ll have more room to maneuver.

We attempt to anchor but then discover we also have an issue with the windlass (used to raise and lower the anchor at the push of a button). So we opt for a mooring ball instead.

Mayreau St Vincent Grenadines
Mayreau, St. Vincent & the Grenadines

Once we are secured, Joel opens the engine hatch and quickly sets about trying to diagnose the engine problem. Dave dutifully hands him tools with one hand, while sipping his recently acquired anchor beer with the other.

I mix myself a fruity rum cocktail (because anchor beers aren’t just about beer) and Nick and Alyssa opt for a refreshing swim.

How to diagnose engine failure…or not

I will paraphrase the next hour for you as I remember it:

Joel: It could be the do-hickey (insert actual diesel engine part here). Let me check that.

Dave: Maybe we’re out of gas.

Joel: It could also be the thing-a-ma-bob (I really hope diesel engine parts are not on the next test). Let me try this.

Dave: Could we be out of gas?

Joel: It’s not this, and it’s not that. Let me radio into the charter base and see what they suggest.

Dave: I think we might be out of gas.

Long story short….we were out of gas.

In Joel’s defense…

He was certain that the charter base had fully fueled the boat before departure. And we have definitely not blown through an entire tank with our limited engine use.

Apparently, diesel fuel gauges are notoriously unreliable (filing that little tidbit away for future reference).

Thankfully, the charter base gives Joel the OK to refuel. The other option is to rely only on sails for the trip back home in a strong headwind tomorrow morning. That doesn’t seem like a great option to me.

He radios ashore and miraculously a cute little fuel boat pulls right up alongside us within 30 minutes.

$180 US dollars later, we are back in business!

Last night dinner in Bequia

Later, we all take turns in Isaphil’s lone shower to clean up for our final dinner ashore.

Joel gives us several options for our last meal in the Grenadines and we choose the Fig Tree restaurant. Mostly because he promised us a string band and dancing.

Fig Tree Restaurant Bequia Caribbean
Fig Tree Restaurant, Bequia

It’s another wonderful dinner further enhanced by one last postcard-worthy sunset. And we all learn that Joel has some mad dance skills.

It’s a lovely way to end the trip.

However, we are all still dreading the final two written tests tomorrow so we head for bed pretty early.

Learning How to Sail, Day 7 – Back to St. Vincent

The sail back to St. Vincent today is short but straight upwind so it’s slow going.

What could have been less than an hour under power takes nearly 3 hours by power-sailing. By the time we make it back to Barefoot’s home base, we are all relieved to be off the boat for good.

We also look remarkably similar to the group I saw last week from our balcony and wondered if they’d been lost at sea. Mystery solved.

Blue Lagoon St Vincent
Arriving back at Barefoot’s charter base in Blue Lagoon

I can’t begin to explain just how much information we absorbed over the course of this past week. My brain is spinning by the time we arrive back in St. Vincent.

But we aren’t done just yet.

Sailing School Final Exams

Now it’s time to lug our suitcases up the hill to the restaurant and tackle the written tests for ASA 104 and ASA 114.

Nick, Alyssa, Dave, and I settle in at a table in the restaurant. After 6 days at sea, I swear this place is rocking. We order lunch and get to work diligently on the written exams.

Two hours later we are finished. ASA 104 was tough but ASA 114 was fairly easy. We celebrate our success with a well-deserved round of cocktails. Make it a double.

Barefoot Offshore Sailing School St Vincent Caribbean
Barefoot Offshore Sailing School

Cheers, sailors!

It feels amazing to finally be done and it feels even better when Joel grades our tests and we all pass with flying colors.

All the hard work was actually worth it.

So, there you have it! Four newly minted sailors, at your service.

And one incredibly exhausting vacation.

I can see now why Joel says some people don’t pass all of the courses on the week-long liveaboard. You really have to be committed to succeed.

Without a significant amount of studying in advance, it’s nearly impossible to absorb it all in a single week.

The Blue Lagoon Resort

Our sailing course may be over, but we’re not done with St. Vincent just yet. In fact, the best is yet to come.

For the next two nights, we’ll continue the graduation celebration just down the road at the lovely Blue Lagoon Resort. The nice folks at Barefoot are even kind enough to give us a lift over (along with Nick and Alyssa to the hotel where they’re staying tonight).

Blue Lagoon Resort St Vincent
The view from our terrace at the Blue Lagoon Resort

We say our goodbyes and exchange contact info with Nick and Alyssa. Then we head inside the resort to check in.

When we get to the room, and I don’t think I’m overstating this, it is quite possibly the most wonderful hotel room we’ve ever seen.

(Upon further review, it is honestly just a nice, standard hotel room. But after a week of living on a catamaran, it seems like the freaking Taj Mahal.)

Air conditioning? Yes!

A king-sized bed? You got it!

Unlimited hot showers? But, of course!

An abundance of functional electrical outlets? Duh!

Wait, even a hairdryer? Stop. Do not toy with my emotions. How else could one reasonably be expected to dry one’s hair?

(I haven’t seen a hairdryer since we arrived in the Caribbean and I may or may not have kissed this one while Dave was looking the other way.)

Lazy days on St. Vincent

We have the best of intentions to spend our last few days exploring the beautiful island of St. Vincent. However, after 5 minutes in this room, we decide we are not leaving it for the next two days.

We even have a beautiful beachfront view from our terrace. Oh, the luxuries!

We take long hot showers and jovially inspect our disturbing assortment of mystery bruises (thank you rough seas!). Later, we lounge languidly in fluffy robes and crank up the AC while simultaneously flipping channels on the TV.

We connect every device we own to the wifi. Just because we can.

It is glorious.

The search for sustenance

But eventually, we realize the hotel doesn’t have room service. So we at least have to leave the room for provisions (that’s sailor talk for food).

Too tired for a real dinner, we settle in at the bar for sunset cocktails and appetizers.

St Vincent Sunset Blue Lagoon
Sunset views from the Blue Lagoon Resort

The Blue Lagoon Resort is also a marina and the home base for two other charter companies. It’s fun to see all the boats and watch the charter guests come and go.

Soon we may be two of those charter guests heading off into the sunset somewhere around the world!

The next day we sleep in and relax by the pool (which we have all to ourselves). We refuse to read a single thing or tie even one knot.

And God help Carl if someone throws him overboard again. He’s on his own.

It’s bliss.

Blue Lagoon Resort Pool St Vincent
The resort’s blissfully empty pool

We watch one last incredible sunset tonight and finally start to feel like this is a vacation!

So, at this point, you might be wondering…

Is a Caribbean sailing school the best way to learn how to sail?

There’s no doubt that a 7-day liveaboard sailing course is the most intensive way to gain an abundance of sailing knowledge in a short amount of time. And the glittering Caribbean certainly beats the pants off any classroom setting.

But be prepared for the work involved if you want to succeed.

The bottom line: If you want to learn how to sail, by all means, learn how to sail. It’s more than just a terrific pastime, it can become a way of life.

Just don’t mistake a “learn to sail course” for a vacation.

Don’t get me wrong, there were plenty of marvelous moments interwoven into our grueling week. Sailing with dolphins, nightly sunset anchor beers, and one pretty incredible lobster dinner.

And even the nights we had dinner on the boat were fun. I could close my eyes and picture cooking a romantic dinner for two on our own sailboat someday after anchoring in an exotic locale. Or island hopping around the Caribbean’s best islands.

Read More: 10 Best Caribbean Islands to Visit Right Now (& Why You’ll Love Them!)

Learning to Sail Caribbean
Certified sailors with the log books to prove it!

But, all in all, learning to sail while completing four intensive ASA sailing courses in a single week is far more work than play.

As it should be. There’s a LOT to learn.

Over the course of the week, Joel continuously emphasized the importance of safety on the water. And those man overboard drills, while we hated them, could save a life someday (perhaps our own).

Looking back, I would do it all over again. There’s no better way to learn to sail than to get out there and just do it.

Day after day, for an entire week.

The next chapter…

By the time our course is complete, we are also able to celebrate the next chapter in our boating life. Our offer to buy the 46’ powerboat we looked at before arriving in the Caribbean was accepted!

We close as soon as we get home.

Bayliner 3988 Portland
Our new boat, soon to be cruising the Puget Sound!

So, very soon we will officially be boat owners!

And though it’s not a sailboat, thanks to these sailing courses we are far more knowledgeable about boats in general. And feeling much more comfortable about our new, floating, second home.

Big thanks to the Barefoot Offshore Sailing School, our excellent instructor Joel and fellow students, Alyssa and Nick. This has certainly been a week we will never forget.

Here’s to years of boating adventures in our future.

Next time with a lot less homework and a lot more anchor beers!


  1. I rarely take the time to read blog posts anymore but this was so interesting, funny, and well-written I stayed for the whole thing. Loved all the details and the pictures. As someone looking to go on a similar adventure this was super helpful!

    1. Thanks, Craig! It was definitely an adventure but I would happily recommend the experience to anyone who wants to learn how to sail.

  2. Irvin Nieves says:

    Hi Marissa and Happy New Year 2022!
    (What a great article written here, I was laughing most of the reading time).

    Currently, I am enrolled in a March course and already paid the deposit. Just wanted to know what are the SVG restrictions, in order to get to Saint Vincent.
    Are the courses still ongoing?
    Any suggestions on what to pack?

    Stay safe and hope to see you all soon!

    1. Hi Irvin,

      Thanks for reading, I’m so glad the post was helpful! I would check with the folks at Barefoot Sailing School directly regarding entry requirement for SVG and the status of courses. Things change so frequently these days with Covid that it’s hard for me to keep up! They’ll have the most current and accurate information. As far as packing, I would recommend that you pack as light as possible. And a duffel bag is best rather than a traditional rolling suitcase since you can fold it up once you unpack in your cabin. There isn’t much space on the boat for a suitcase. Sunscreen, hats, sailing gloves, and lightweight clothing are all good things to pack. Hope you enjoy your course, it’s definitely a challenging but very rewarding experience!

      Best – Jenny

  3. Nicole Boucher says:

    Thanks so much for such a detailed review! It was very helpful! My boyfriend and I just booked this course for March 2022. We currently live on our power boat in Rhode Island and have been thinking of switching to the catamaran lifestyle and moving to warmer waters. I think we will be staying in the area for 3 nights after our course (mostly because of limited return flight option but also to relax and explore). I was wondering if you had any recommendations of where to stay either on Saint Vincent or over on Bequia (open to other islands with ferry service as well). Looking for something nice but reasonable maybe $200-$300 per night, and will definitely need a hair dryer!! ☺️

    1. Hi Nicole! Thanks for reading, I’m so glad it was helpful. For hotels, we did like the Blue Lagoon Resort (https://www.booking.com/hotel/vc/blue-lagoon-and-marina-ltd.en.html?aid=848545&no_rooms=1&group_adults=2) where we stayed after the course. It was pretty affordable, around $150/night. For Bequia, try Sugar Reef Bequia (https://www.booking.com/hotel/vc/sugar-reef.en.html?aid=848545&no_rooms=1&group_adults=2), it’s an adults only property with gorgeous water views and it’s $200-300 a night. Honestly, either will feel like the Taj Mahal after a week on a catamaran, ha!! Enjoy the course, I’m sure you will love it!

  4. What a Wonderful and fun article to read. Loved your writing and I was able to picture mysel in one of these courses. I’ve been in the powerboats for 30+ years but, Sailing is Sailing!!! Currently, I am planning to take them soon and Thanks to your stories, I will be doing it sooner than expected. So, see you in the waters, Sailors! God Bless you All!!!

    1. Thanks so much, Irvin! Good luck with your sailing courses, it’s quite an adventure!

  5. Marissa Barnard says:

    A lovely post. Thank you for sharing your adventures! We loved having you join the school and hope to see you back in the islands again sometime! Congratulations on your new boat! I am sure you are both confident and competent boat captains now. Philip, Marissa and the Barefoot team and family.

  6. LYNN ROBERTS says:

    Thanks for the article. Laughed out loud at most of the posts and now excited about the adventure. We are taking this class in April-June timeframe, whenever we settle on a date, with Covid, etc. The study books arrived today! We are considering taking the 101, in advance, as you suggested. Please contact me on what we can do beforehand, what to pack, not pack, etc., to make the trip a success.

    1. Hi Lynn! It’s definitely a plus that you’ll have lots of time to study before you go. I wish we had studied more, it would have been a lot less stressful! You’ll want to pack as light as you can and try to use just a duffle bag since there’s very little room for storage on the boat. Bring anything you might need for seasickness, we had a few rough days out there (our captain had some ginger which helped me). If you can do 101 in advance it’s a huge help. And buy some line to practice knots before you go. Just having all the terminology down and not having to practice knots as you go will make the whole experience easier and more fun. I would have enjoyed it more if I hadn’t been so stressed about the coursework! With that said, they do a great job and the Grenadines are incredibly beautiful to explore. I hope you guys have a wonderful time!

  7. Thank you for this awesome blog! How ironic, that we are also from Seattle….just sold our Bayliner 4087 and are looking to take this course this October. This was very helpful and we appreciate your insight! ~ Scott and Ally

    1. Hi Ally, glad it was helpful! Such a small world. We are actually getting ready to sell our 3988 in Bremerton. We love it so much but with COVID now we haven’t been able to get out there in months so sadly it’s just been sitting empty. It’s such a great boat I feel like someone should get to use it so we decided to list it. Plus my husband now has his heart set on a future catamaran purchase, ha! Good luck with the course, it’s definitely a one-of-a-kind experience!

  8. Thank you for reporting on your adventure. I have wanted to do this for years and now have a better idea what to expect…guess I better do the homework prior.
    Thanks again
    Charlotte. NC

    1. You’re welcome, Mark! Yes, the more you study in advance, the more you will enjoy the experience. (I wish I had studied more!) Hope you have a great time!

  9. Thank you for writing about your experience. It’s very helpful to know what to expect. I was wondering when did you take this course? What month and year? Thanks.

    1. You’re so welcome, Liz! We took the course in February of 2017. It was definitely intense but we learned a lot. It helps a ton if you read the workbooks and study a lot in advance. I wish I had studied more than I did before we left. Good luck, hope you enjoy it!!

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