Of pirates, palm trees and big plans: the Caribbean sailing guide for beginners

Of pirates, palm trees and big plans: the Caribbean sailing guide for beginners

Island hopping from the BVI, the Bahamas, Cuba breathing in the best sailing Caribbean tips

When Christopher Columbus first set foot on the soil of what he thought was India in 1492, entering the "New World" for the first time (in what is now the Bahamas), he was probably unaware of what a paradise he had discovered. And even if he was, it was undoubtedly a long way to the place that is the definition of a holiday paradise for so many sailors today.

In the centuries following this historic event, the Caribbean was a place for adventurers and pirates, slave traders and plantation owners, the scene of conflicts, the source of untold riches and a place where the rigid class structures of old Europe sometimes became blurred. A place where pirates, privateers and settlers sought wealth or freedom, happiness or even just a new beginning. And where the powers that determined the course of the world at that time fought out their conflicts. First the Spanish, then the French, British and Dutch. They all left their mark on the islands' heritage, which has lost none of their fascination over the centuries.

And anyone who swims underwater with a snorkel or takes a dive today will find the legacy of those who sailed through these waters. Where divers today enjoy the fascination of the underwater world in the Caribbean, the wrecks of proud ships are tourist attractions that show how merciless the competition between nations was.

Where once you'd find gold, tobacco, sugar ear, rum and people trading, today a true paradise opens up to those relax- and holiday seekers. Who wants to reach the most incredible places under sail and seek ultimate relaxation on white dream beaches with a painkiller in their hand? 

A diverse ecosystem of islands 

As diverse as the powers that shaped the region's destiny are the influences of the colonial power resident on each island. Whether Spanish, French or English in character, the friendliness of its inhabitants, the hospitality and the relaxed rhythm run like a red thread through the island world off the coast of the American continent. Whether in the excellent cuisine or the official and Creole languages, the details and nuances, the sound and taste, the mentality change everywhere according to the colonial heritage. And that is precisely what makes this region so fascinating.

So many stories and legends entwine around the hidden beaches, ubiquitous coral reefs and other places at sea and on land. We could probably write an article purely on those stories from around here. This article is about to give you a brief introduction and overview of the islands, a quick look at the land and the people, at nautical and sailing aspects, at culinary and cultural aspects (above all it doesn't claim to be exhaustive, although we'll hope you'll find it enjoyable!). A short journey through the waters that are the setting of Robert L. Stevenson's Treasure Island, which Johnny Depp as Captain James Sparrow made unsafe in the film representing all literary pirate characters. Parts 1-3 were actually all filmed there and still exude a whiff of the adventure that many of us seek and find when sailing. So light up a Cuban cigar, pour yourself a glass of rum and join us in discovering the fascinating island world.   

What’s it like to sail in the Caribbean? 

The Caribbean consists of more than 5,000 islands, reefs and coral reefs. Here you will find everything and (almost) every challenge you could wish for as a sailor, and at all levels of difficulty. From simple navigation on sight to demanding bluewater sailing - no wishes remain unfulfilled here. A great adventure playground where you can find a place to feel good with every level of experience.

The Caribbean arch offers protection from the big Atlantic waves. During the high season between November and April, there are constant trade winds, little rainfall and no tropical storms. Ideal for escaping the winter in Europe. When it gets grey and gloomy here, the island world usually shows its best side.

Around the Caribbean islands, you will often find larger shallow water spots, making it an ideal catamaran destination. But also with a sailboat, you can discover the areas, which guarantee perfect anchorages and great sunsets with their countless dream bays.

But here, too, the rule applies: the details and the degree of difficulty vary from sailing area to sailing area. A reason for us to introduce you to the most important ones. 

The British Virgin Islands

The islands are considered the ideal sailing area for an introduction to the Caribbean. Tropical idylls that live up to every cliché. Enchanting islands, blue seas, dream beaches, and despite Hurricane Irma, which unleashed its immense destructive force in 2017, some excellent facilities for sailors. The 60 islands of the British Virgin Islands archipelago are not far from each other, no clearing in and out, and the area offers good shelter from the big Atlantic waves. Even after the hurricane, the islands are well on their way to becoming a top spot in the Caribbean sailing realm.

The short distances, the marinas and harbours, and the buoy fields could bring back memories of those in the Mediterranean Sea. If you need it, you can always find a bar or restaurant on the beach. These ratios, unique by Caribbean standards, bring a lot of popularity. As a result, prices and the number of charter yachts are relatively high. So a buoy field can be full even in the afternoon. You can rent a catamaran or a sailboat to explore the islands. 

British Virgin Islands

The Bahamas 

Over 700 islands, only 30 inhabited and well shielded from the Atlantic and its waves: that's the Bahamas. The distances here are short, and the palm islands entice with their fine white sandy beaches and plenty of entertainment in the form of beach bars, resorts and marinas, which is especially true of the so-called Abacos. While the Exumas, the southernmost area, remains much more secluded.

Both areas are about 200 nautical miles apart, and those sailors wanting to experience both have to bring along some time to take in both. The distances between the destinations are short within each district, although you can take longer routes at will. The long island chains offer sufficient shelter from open Atlantic waves. The shallow stretches of sea between the islands shimmer turquoise, an ideal catamaran spot. With a single-hull keel yacht, the situation is somewhat different; here, you must always keep an eye on the depth gauge.

Underwater in the Bahamas

The Leeward Islands

We mentioned the diversity of the Caribbean above, and nowhere is it more well documented than in the Leeward Islands. Saint Martin, Sint Maarten, St. Barthélmy, Anguilla, St. Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Montserrat stretch out over a good 200 nautical miles: former English, Dutch and French colonies cluster together in a clear area. And those with high sailing standards can look forward to exciting passages on the open Atlantic.

Of course, you won't be able to make it to all the islands. Quite a lot for one cruise. It often makes sense to put two neighbouring islands on the list of destinations. Antigua and Guadeloupe, for example. 

St. Martin, the island with French and Dutch sides, is the epicentre of sailing tourism in the Leeward Islands. Here you will find the bases of the charters and all sailing facilities. You can reach St. Martin by direct flight from some European countries, e.g. from Paris or Amsterdam. Alternatives for the start of a cruise include Guadeloupe or Antigua. 

The Windward Islands

A classic amongst the Caribbean destinations is the Windward Islands: Martinique, St. Lucia, St. Vincent and the Grenadines and Grenada. This chain of islands stretches for a long time in the south of the Caribbean Arc. If you sail back and forth between the large islands, it can take up to 5 or 6 hours. Over 150 nautical miles of pure Caribbean await you. Sailors report feeling the Atlantic waves. It is usually much calmer on the west side: distances are shorter, as between the many small islands of the Grenadines.

Martinique is an excellent place to start, but the Grenadines, with their picture-book Caribbean charm, can be the endpoint of a two-week cruise. If the time budget is not so high, you can also set sail from St. Lucia. 

The Windward Islands


"La vida es corta pero una sonrisa sólo precisa un segundo", life is short, but the effort of a smile only takes a second. A Cuban proverb. And when you talk to returnees about sailing in Cuba, you often see such smiles. Enthusiasm sticks - and usually, it is not only the sailing experiences that make them reminisce. What makes the largest of the Caribbean islands so popular are the numerous offshore islands, the Cayos. There are said to be over 1000 of them. There is hardly any infrastructure when sailing in Cuba, but nature parks and untouched nature in front of a dreamlike Caribbean backdrop attract visitors.

 If you visit Cuba, you usually can't miss Havana. The capital of Cuba, characterised by the Spanish colonial architecture of the 16th century, is the Caribbean metropolis par excellence with its approximately 2 million inhabitants. A city of contrasts that is worth a visit.

Cuban music's everywhere

Find what suits you best!

One could argue that sailing in the Caribbean is a bit like going to a buffet: plenty of choices from beginners to experts where one can pick what suits them best. While beginners and harbour hoppers will find excellent facilities in the BVIs, for example, explorers will get their money's worth in Cuba. And if you are looking for a sailing challenge, choose an area with long Atlantic passages between the islands. And if being on the water is not enough, we recommend one area in particular: the second largest reef in the world in the Caribbean. We're, of course, talking of the Belize Barrier Reef, a true paradise for divers who also want to be underwater.

Curious? Our experts will be happy to answer all your questions, visit our boat listing page the Caribbean Sea, chat to us via the chat box or call us on +44 20 8068 4904 

Magister Navis International Issue number 3