My Sailing Experiences and Chartering Boats in the Caribbean

My Sailing Experiences and Chartering Boats in the Caribbean

Quite unfortunately for me, I did not grow up learning to sail. I was busy practicing ballet, taking horseback riding lessons, racing around town on bicycles and, later, skiing. In any event, I couldn’t have learned sailing as a kid anyhow because my family always lived in land-locked states.

When I was 11 years old, however, I had my very first experience sailing during a family summer trip through Maine Our family met up with a friend of my father, at the friend’s glamorous parent’s home on the coast. His parents took us all out sailing and even let us sleep on their sailing yacht one night.

I immediately loved it all. It suited me perfectly since I was always enamored of water, nature, rigorous exercise and adventures.

Of course for that sailing adventure I was just a child passenger on the boat. But it sure was fun! I hoped I’d be able to sail more someday. .

In my adult years I’ve seen young kids learning to sail at St Petersburg, FL Sailing School as well as at many other yacht clubs and sailing schools around the world. I always look on with a bit of curiosity and jealousy. How nice it would be to grow up sailing!

I’ve also seen (and met) young adults and teenagers who are so adept at sailing that they can competently handle a boat solo and even oversee a crew. These are young yachtmen who’ve been sailing since childhood so that handling a boat is second nature to them. Some even own their own sailboats by age 18.

I did eventually get to take up sailing, but not until much later in life. And that was almost entire due to my mom and step-dad…

My parents’ sailing life

My parents divorced soon after I left home for university. My mom re-married a few years later. In the early years of their marriage, over 25 years ago, they took up sailing.

Over the course of several years, they took a whole series of sailing courses in Anapolis, Maryland on the Chesapeake Bay. They started with basic sailing lessons recognized by the Sailing Association of America (ASA) and progressed up to advanced sailing, navigation, night navigation, various weather courses, safe boating, rescue skills and many other sailing subjects.

During their training, they read many detailed sailing course books, watched videos and, most importantly, practiced sailing on yachts in the Chesapeake Bay, along with their instructors and sometimes with other sailing students.

Throughout their sailing education and adventures, I was a mere distant onlooker. At the time, I was living in Kyoto, Japan.

Throughout those years of sailing training and practice, they were living in another landlocked state, so they never had the opportunity to buy a yacht of their own. Instead, they sailed during lessons and also began chartering sailboats on their own or in conjunction with other sailing couples they’d met.

Chartering Yachts

Since most of their sailing experience and training was in the Chesapeake Bay, when they started sailing on their own, they began chartering yachts in the bay. That gave them plenty of experience comandeering sailboats in a huge body of water.

Eventually they decided to go further afield, to the Caribbean. They hooked up with members of their sailing club, headed down to the British Virgin Islands and chartered themselves a yacht to sail for one week around BVI islands.

They had mostly smooth sailing, greatly enjoying the beautiful Caribbean turquoise seas, powdery beaches and idylic tropical islands.

But they also ran into several smallish, but potentially serious situations. First off, the two couples did have some troubles getting along, as they had different personalities and outlooks on handling the boat. But they all managed well enough as reasonable, flexible adults.

And of course, they ran into some rough weather, some rough waters, and thoroughly put all their sailing education and experience to good use.

They also had a minor pirate experience! Two completely unknown, unidentified men in a speed boat approached their yacht; asked to board their boat, claiming they were interested in buying it; climbed aboard, rifled through all their drawers and cupboards; then, thankfully, left without further ado.

Another day their engine gave out when they were trying to navigate through some shallow, rock-strewn waters. They had to call their charter company, who motored out to their yacht and fixed the engine for them.

But overall they had a wonderful time sailing around the Caribbean.

My parents’ yacht

Soon after their first Caribbean chartering adventure, they moved to a new home further from Anapolis and the Chesapeake. So for the time being, their sailing adventures came to a halt, though they did charter a boat up on Lake Superior one summer.

Several years later they moved down to St Petersburg, Florida. My step-dad promptly bought them a decent sailboat, fulfilling one of his lifelong dreams. They joined a local yacht club, docked their boat at a local marina, and began sailing regularly in nearby bays.

That was over ten years ago.

My introduction to sailing

As a result of their move to Florida in 2011, whenever I return to the States now to visit family, I get to hang out in wonderful, beautiful Florida, the Sunshine State. In addition to the many fantastic things to see and do in St Pete, I also finally got my chance to learn sailing.

My parents had gradually slipped into sailing less regularly. But when I visited in 2015 for an extended stay (six months), it was very easy to convince them to start sailing regularly.

We began sailing every week on the local bay. They taught me everything about sailing their boat, from prepping the boat to sail, carefully maneuvering the boat out of the slip and marina, handling the sails and boom, understanding the wind, navigating the boat back through the marina and into their slip, and even skippering (driving). It was great fun.

At the same time, I rigorously poured over all their sailing course books, learned all the parts of the boat and boating terms as well as basic navigation and how the boat functions. I also watched dozens of sailing videos that my parents had in storage.

In addition to weekly sailing with my parents, I found out about weekly ‘beer can racing’ at the municiple marina. In those casual sailing races, regular citizens with their own boats go out racing on Friday evenings. They usually need more crew to help handle their boats, so anyone interested in going out sailing can show up and try to help crew a boat.

I began going every Friday evening to crew the races. After a couple weeks I found a captain and boat who were happy to have me aboard, so I ended up sailing with them every week for several months.

So with weekly leisure sailing practice, weekly racing and daily studies, I really immersed myself in sailing for half a year. I also took a Safe Boating Course from the US Coast Guard and got licensed as an official Safe Boater. Woo-hoo!

After all that sailing education and practice my next goal was to try crewing some boats in the Caribbean. I hoped to find a boat heading out of St Pete down to the islands.

However, that proved harder to find than I’d hoped. Despite joining my parents at their regular yacht club meetings, getting to know various other people who sail and befriending one guy who worked at the St Pete marina, I never did find a boat to crew that year. Instead I ended up flying to Guatemala.

I did sail with my parents and in the sailing races during the next two years whenever I visited family in Florida. But I never stayed as long as in 2015.

Unfortunately, I haven’t sailed much in more recent years. Sigh. But I’m still hoping to sail more in Florida and in the Caribbean one year soon.

Meanwhile, I have made some progress exploring the Caribbean islands. I’ve made three separate trips: I spent one month in Cuba, two weeks in Puerto Rico and two months at Aruba.

Sadly, no sailing during any of those trips. Maybe next time I head down there I’ll be able to combine island visits with sailing. Fingers crossed!

Meawhile, I’ve also learned a lot more about sailing in the Caribbean and chartering boats there…

Chartering yachts in the Caribbean

Throughout the world, there are several major sailing areas and the Caribbean is one of them. In fact, the Caribbean has the most-developed chartering business in the whole world.

In global terms, the Caribbean Sea is a rather small sea. But it still covers a vast, vast area and includes several dozen independent island nations. They’re scattered across the Caribbean between the USA and South America.

Within the Caribbean, there are several major sailing regions, including British Virgin Islands, US Virgin Islands, the Bahamas, St Martin, the Grenadines and others.

So anyone considering chartering a boat in the Caribbean should first decide where they want to sail. After that, there are several other important considerations to make.

First off, there are many different types of boats that can be chartered. There are sailboats, catamarans and several types of power boat yachts. Boats are further distinquished by their size (total length), quality and age. These factors all go into the price of chartering.

Then there are different types of charter options. ‘Bareboating’ entails completely chartering a boat yourselves, like my parents and other experienced sailors often do. To charter a boat without its attendant captain or crew requires proof of sailing education, at minimum.

Hopeful sailers without training, experience or confidence can charter a boat with a captain only or a captain and full crew. A ‘skippered charter’ is a boat with a captain only, generally with the customers crewing the boat under the skipper’s command.

A ‘crewed charter’ is a boat with a skipper and full crew, including deckhands, a cook and often a mechanic. In these charters, the customers just sit back and enjoy the ride, dining and activities, while being fully waited on.

Regardless of the destination, type of boat and type of charter you decide on, one very important factor is to choose an excellent charter company. You want to make sure they have high-quality boats that are in great condition and not old.

A good charter company can also help plan your sailing itinerary & route, give you safety advice, provide good land facilities and be prepared to help out quickly and efficiently with any problems that may crop up during your trip.

My parents’ experience with their bareboat charter in BVI illustrates how important it is to choose the best charter company. Their boat turned out to be older and not in tip-top shape, thus leading to the engine breakdown and a long wait to be ‘rescued’ by the company.

Apparently the company also did not warn them about potential pirates in the area and how to handle such situations.

Sailing around the Caribbean can be a wonderful adventure and beautiful nature immsersion experience, as my parents will readily attest to. Charter companies are easy to find and every type of boat and charter is available.

It’s well worth taking a Caribbean sailing vacation. Just be sure to choose a highly-rated charter company and to make the best decisions about destination, boat type and charter type for your interests and experience level.

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