The Idea

Learning to sail from Grenada to the Tobago Cays may sound advanced for a first time solo traveler, but it was far less scary than being a passenger on a tour bus, hopefully looking around and praying you’re not the only person without a plus one.

Exploring Grenada, Grenadines, and Tobago Cays by boat was also a nice draw.

Planning and Research

Somewhere along the line of me deciding to be an “adventurer”, I had it in my head I would learn to sail.  Yacht Ibis was one of the search results and had the advantage of learning to sail while on vacation. 

Learning to sail while island hopping from Grenada to the Tobago Cays seemed like the perfect trip for a solo traveler. 

I especially liked that the site was clear it’s about having a good time and coming away with a new skill.

Here I was in my thirties and a size 16 thinking I wasn’t the standard type of person that booked this trip.  But I continued to cyberstalk the website and give myself pep talks. 

Finally biting the bullet, I hit the “I’m in” button. 

My nerves kicked in almost immediately and I completely over-researched and overthought everything.  The upside to this is that I felt prepared, although I did have a moment of “What the hell am I doing” on the airplane.

Prior to the trip, I didn’t want to ask too many nosy questions like how many people would be sailing with me.  This was mainly because I didn’t want to sound like a crazy, paranoid person.

I appreciated that the Yacht Ibis team always answered my questions and made me feel like this was normal.

Arriving in Grenada

When our captain, Sam Bartlett, greeted us at the airport, it surprised me there was only one other person, but Sam shared that this was unusual and her next two trips were already full.  It seemed the timing just wasn’t good for many people.

Our adventure started on the Bleu Turquoise, a 50 foot high-performance sailing yacht.

Since there were only two of us plus Sam, we each got our own cabin.  Mine had a huge bed, teeny-tiny closet, and even teeny tinier bathroom. 

The team sends out helpful information ahead of the trip and there is a lot of information on the website,  including preparing me for the small quarters.

Downtown Grenada for Supplies

After unpacking, we walked to the market in downtown Grenada for supplies.  If you are in the area, it’s definitely something to experience. 

Stalls and tables full of brightly colored clothing, exotic fruits, and spices for sale fill an entire section of town.

It’s similar to a Farmer’s market, with some vendors in a central area, but others are randomly on the sidewalk.

Since Grenada is well known for its nutmeg you can find it everywhere and I would recommend taking some home. 

We headed to the fish market which is a large warehouse full of vendors selling fresh seafood.  By the time we left the market, we had plenty of fresh fish and vegetables.

I’ll give you a little teaser here and tell you that the food on the trip is phenomenal. Sam is an exceptional cook and I’ve heard other members of the team are equally skilled.

Our First Sailing Lesson

That afternoon, we took Bleu Turquoise out for a spin to begin learning the ropes.  Sam taught us some basic knots and how to raise and lower the anchor, then we were on our way. 

Trust me, you’re in good hands with the Yacht Ibis team.  We practiced steering and got a feel for the boat.

The Bow of our sailboat as we pulled into a harbor for the night

We anchored near an underwater “park” where statues hide underwater for you to find as you snorkel.   

At first, you don’t see anything since your fins are kicking up sand, and you begin to wonder if you will ever find the statues. 

Out of the blue, you turn your head and almost swallow water because a giant bronze head is right next to you! 

Then you see the group sitting in a small circle and a little further away, a larger circle, then others in various positions. 

Underwater statues while taking Bleu Turqoise out for our first sailing lesson

It becomes a treasure hunt to see how many you can find.

I was beginning to sense that this trip was going to be a mix of learning to sail and having amazing experiences.

Heading to the Grenadines

If you’re learning to sail from Grenada to the Tobago Cays, then you’re going to sail through the Grenadines.

That was our first stop and we set out early in the morning. 

It’s about 4 hours to the main island in the Grenadines where you have to check-in and get your passport stamped.  

It was surprising to me that you can’t just sail through to your destination.  There are strict rules and you need to check in just as you would traveling to a country by any other means.

Sam warns you about seasickness because there is a lot of time with nothing to help orient you spatially. 

I thought I’d be fine since I’m not usually prone to motion sickness, but after 2 hours of just ocean and horizon, my head and stomach weren’t lining up and I finally succumbed. 

My recommendation is to have some medication with you.  That definitely helped and I was fine the rest of the trip.

Once I was feeling better, I was able to enjoy the view. 

The scenery is just like in movies: blue ocean, shadows of islands in the distance, waving at other sailboats and catamarans going by, all under a perfect blue sky.  The ocean was incredible. 

I’ve been to places like Hawaii and seen bright blue ocean, but this was different.  The color changes depending on depth, temperature and current. 

It can range from aquamarine, to green, to turquoise, to a deep blue, or even almost clear.

It was great to have something to do as we sailed.  Sam continued our sailing lessons, showing us how to manage the sails and move them into the wind.

A Few Stops Along the Way

On our way, we stopped at a small island that looked like a large sandbar in the middle of the ocean. 

It was long and narrow.  We anchored the boat and snorkeled to shore. 

Once we walked out of the water, the narrowness became obvious as you could see the other side of the island less than 100 feet away.

Throughout the trip, we saw several of these little sand areas with trees.  One, in particular, looked like the cartoon picture of someone stranded on a little circle of sand with a single palm tree in the middle.  

It was clearly man-made, but definitely entertaining.

Exploring the Local Towns

Anchoring in the Harbors

As we were learning to sail from Grenada to the Tobago Cays, I realized that you don’t just anchor in the ocean or keep sailing.

Each evening, we headed for a small harbor where we would anchor for the night. 

When we pulled in, Sam took the helm and we each set to our jobs.  My sailing companion would begin lowering the sails since he was taller and I would lower the anchor. 

I’m proud to say that I am excellent at anchor lowering and raising, which is not as easy as you may think. 

You have to pay close attention to the captain and count the flags as the anchor quickly lowers.  The chain can also become tangled and you have to be ready to quickly fix it.

The Local Towns

A few of the harbors had small towns, and if we had enough daylight left, we would take the dinghy to shore and explore.

While the majority of the trip is picture-perfect, as you go into the towns and explore past the touristy areas, you see a lot of poverty. 

It’s a reminder that island living isn’t always the dream lifestyle many of us imagine. It has its benefits, but there isn’t always a healthy year-round income stream.

The brightly colored tourist shops are right at the dock where you tie up the dinghy. Small groceries and markets for locals are usually further up the roads.

We would often come back to Bleu and jump off the back for a swim to cool off before heading back out to dinner. 

Most of the time we ate at a local restaurant, many of which had docks you could pull right up to with the dinghy. 

The food was always amazing with fresh flavors, spices, and excellent preparation.  I can’t recall one bad meal the entire trip.

One thing I noticed is that costs are higher than you may anticipate.  Many items are difficult to bring in which raises cost and the locals need to compensate for the fact their business is seasonal. 

I felt that I got my money’s worth at meals, but make sure you bring enough local cash before setting out.

The Tobago Cays

After spending time exploring the Grenadines, we continued to the Tobago Cays.  This was, by far, the highlight of the trip. 

The Cays is a truly beautiful area and earned a spot as one of my favorite places of all time. 

The water is that perfect aquamarine blue you see in pictures of faraway beaches.  The water temperature is comfortable enough to explore for hours.

Tons of coral lie right beneath the surface and you have to weave your way through it.

Exotic fish I’ve only seen in aquariums swim under and around you.  We saw manta rays swim by and bury themselves in the sand. 

There were also sea turtles in protected areas we could snorkel alongside.

We actually had such a good time in the Tobago Cays that we opted to stay an extra day. 

That’s the other advantage of this type of vacation.  As long as everyone agrees, the schedule is flexible and you can modify the adventure as you go. 

To end the perfect trip, we capped off our last evening in the area with drinks at a fancy resort.

The Moment of Realization

Even though the vacation was learning to sail from Grenada to the Tobago Cays, I realized it was more than that. 

We were learning what it was like to be a sailor.  How to live on a boat, the good and the bad.

I recall one afternoon hanging out in the water, enjoying the day, but having to swim back to the boat every few minutes as the current kept carrying me away. 

Sam threw me a line which I tied around my waist allowing me to lay back and let the current gently pull me, but only so far. 

For an hour, I experienced a sense of complete relaxation. 

Here I was in crystal blue water, a bright blue sky, gentle breeze, and picture-perfect scenery letting a current gently try to take me out to sea but not succeeding.

I realized that all of a sudden my age and weight were meaningless. 

Everyone was having their own great time.  I could be me and not worry, there was no judgment, just different people enjoying the same trip. 

We would all part ways afterward.

Heading Back

Sadly, it was soon time to turn and head back to Grenada. 

By now, Sam was letting us take on most of the sailing.  I’ll never forget my turn at the wheel, steering the boat at a 45-degree angle into the wind. 

There was a surge as the boat heeled (a fancy term for tilted to the side) and then took off at 10 knots.  It was an awesome moment. 

Even though it’s not driving a car on a highway, it feels fast as the wind rips through the boat. 

It only lasted a few minutes before we lost that perfect angle, but I can still recall the feeling of the wind catching the sails.

It took two days to return to Grenada. Once docked in the slip, we were able to use the individual shower rooms at the marina. 

On the boat, a “shower” is usually a quick suds with the freshwater hose on deck after your last dip in the ocean. 

While you don’t really feel dirty, that first real shower with hot water under pressure is glorious.

Exploring Grenada

Check out our post for the full story on my one day adventure in Grenada

Since we had an extra day before our flights, Sam reached out to her contacts and arranged for a tour of the island with a local guide. 

While our guide knew what he was doing, I couldn’t look at the road without worrying we were going to tumble off a cliff. 

The roads are narrow, full of deep potholes, and there are no guard rails.  It’s you and the cliff.  We never had anything close to an incident, but it’s a lot different than driving in the US.

Our driver took us everywhere.  In one day we visited a chocolate factory, toured a rum distillery, a local park, several small towns known for different specialties, and a mango grove. 

All of this with a history lesson of the island, the people, the animals, and the flora.

It was Mother’s day and most of Grenada was shut down for the day.  The restaurant at the chocolate factory was full but they let us in. 

Later we realized that due to a translation mishap they thought we were a couple and had children. They weren’t going to let a “mother” go without being celebrated.

The island has a strong family culture which was evident that day and I’m glad we got to experience it firsthand.

Heading Home

The next morning, as my flight took off, I looked down and was able to recognize many of the different areas we had visited.  

I had over 3 hours to think about my trip and realized solo traveling isn’t scary or sad, or pathetic.  Solo travel is crazy, flexible, and fun.


Researching and booking were easy. 

The Yacht Ibis website has had improvements from when I booked, however they maintained their calendar which is clear and easy to follow.  

I was able to look at the schedule and find a suitable trip for my skill level (complete beginner) during the month I could take vacation. 

To book, I simply hit the book button and then sent an email. Payment instructions are clear and well spelled out, especially if you’ve never transferred money to a bank account outside the US.

Once you book, you will receive a packet of helpful information.  Take the time to read through it. 

Yacht Ibis does an exceptional job in helping you prepare.

To learn more about Yacht Ibis and see upcoming trips, check out their website:  Yacht Ibis


The Internet is quite limited when you’re sailing and while the boats are out on the water, it’s difficult for Sam to reply to email. 

Enter the amazing Hazel, who is now listed on the website as the Communications Director.  Hazel was great about getting back to me and answering my questions. 

She had been on multiple trips and was familiar with sailboats so she was able to step in and take care of all my questions.


The flight to Grenada was easy.   I also booked a hotel on either end of the trip. 

You can stay on the boat if you’d like the day before and after the trip.  There was some confusion about whether it would be in dock when I arrived, so I chose the hotel. 

Sam greeted me and the other person on the trip at the airport and got us settled.  In the morning, I got a ride to the marina and followed her instructions to easily find Bleu Turquoise.

Things to note

Pack a duffel bag, not a suitcase.  There is no room to stow a suitcase and getting it on/off the boat will be difficult. 

You’ll need sunscreen and lots of it.  I would recommend a biodegradable soap and shampoo for the few times you’ll need them.

Follow the instructions you’re given and take the packing list to heart. 

Even if you’re not prone to motion sickness, consider having something like a patch or other motion sickness medication.

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2 Responses

  • This post says so much more info than other people, and it’s very useful to me. Will follow you to see more writing from you! is it okay to share this?

    • Thank you so much for the kind words! I’m still getting the hang of the website and just added buttons to share via FB/Twitter/LinkedIn — so definitely please feel free to share. I’m hoping to post more trips shortly.

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