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Cruising Guide: Caribbean

By our travel expert Mike

The Kraken quick-fire guide to sailing in the Caribbean.

Watch any 90s holiday TV show and you would have thought that the Caribbean is all the same, long white beaches hosting sprawling hotel resorts with poolside cocktails on tap. But this is far from the whole story.

This beautiful tropical region of more than 700 islands stretches across no less than 13 lines of latitude creating a region of ecological, geological and cultural diversity.

Every time I visit a new part of the Caribbean, I’m blown away by the individualism of each island. Which makes choosing where to sail in the Caribbean is not as easy as it may seem. You need to decide what you want out of your holiday, and then find the right area to explore by yacht.

Luckily, we’re here to help with our quick-fire guide to the sub-regions of the Caribbean. Let’s go from North to South:

Lucayan Archipelago

Rule of thumb, the further North you are, the more “Westernised” the Caribbean feels. Sitting a stone’s throw off the Floridian coast, The Bahamas are a great sailing ground – but make sure you have a shallow draft yacht or catamaran. Sailing between its pristine islands, the protected turquoise waters are home to sea turtles, nurse sharks and schools colourful fish. The sailing here is sheltered and easy, with well serviced amenities ashore.


The Bahamas, Turks and Caicos Islands
Yacht Charters Adventures In Caribbean
Yacht Charters Adventures In Caribbean

Greater Antilles

The previously mentioned “rule of thumb” goes out the window here… The Greater Antilles are home to an area of great Spanish influence. The long island of Cuba is fairly new to the yacht charter scene. Its rocky coastline is peppered with long, jagged reefs. Navigation can be tricky, but get behind the breakers and dive off the boat to experience some amazing snorkelling. To the East of Cuba is Puerto Rico. Taking a yacht from Puerto Rico’s Eastern shores and you’re into the Spanish Virgin Islands. Previously untouched by developers due to the US military using the islands for bombing practise until 2003, the Spanish Virgin Islands remain largely untouched and offer a unique chance to explore the wilderness ashore. These islands offer a sense of rawness and a natural Caribbean charm, somewhat akin to what the British Virgin Islands may have been like thirty years ago.


Cuba, Puerto Rico, Spanish Virgin Islands
Yacht Charters Adventures In Caribbean
Yacht Charters Adventures In Caribbean

Leeward Islands

This is the heart of sailing in the Caribbean. Close enough the US to be well equipped with essential amenities, yet far enough away to have a sense of Caribbean liming (relaxation). Yet even within this sub-region, there is a big diversity in the personality of the islands. The USVI and BVI are great for “line of sight” sailing, protected anchorages and legendary nightlife ashore. With no shortage of rum shacks, boutique restaurants and upmarket resorts, you can easily tailor your charter to your needs.

Heading South to St Martin/Sint Maarten, this Franco-Dutch divided island is one of the most popular sailing destinations in the Caribbean. Ashore there is everything you could want from a glitzy holiday with fine dining, nightclubs and casinos – all with a Euro-Caribbean twist. Want to relax a little? It’s just a short sail to the tranquil shores of St. Kitts and St. Barths.

With 365 beaches, clear blue waters and a packed regatta calendar,  Antigua really is the home of yachting in the Caribbean. From the UNESCO Nelson’s Dockyard, you can explore an island steeped in history and natural wonder. Ancient shipwrecks pepper the coast creating a perfect place to dive alongside the abundant natural reefs. For those seeking something a little different, head offshore to the active volcanic island of Montserrat.


US Virgin Islands, British Virgin Islands, Antigua, Sint Maarten, Saint Barthélemy, Guadeloupe
Yacht Charters Adventures Worldwide
Yacht Charters Adventures Worldwide

Windward Islands

The Windward Islands have a truly relaxed french atmosphere about them. Starting in Martinique, this luscious green island has everything you need to enjoy a holiday and is delivered in a very relaxed but functional manner. The coast is home to a number of pretty seaside villages where charming cafés and mouth-watering boulangeries sit alongside Creole restaurants serve a cosmopolitan mix of French and West Indian food. Head down to St. Lucia, St Vincent and the Grenadines, and the Caribbean feel ups a notch once more. The shore-side resorts are less frequent and the landscape is breathtaking.

Head south of St. Vincent for the stunning Tobago Cays, where you’ll find a small archipelago of deserted islets with some of the best diving and snorkelling in the world. The dazzling powder-white sands are home to many-a-beach BBQ to cook your freshly caught lobster on.


Martinique, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Tobago Cays
Yacht Charters Adventures Worldwide
Yacht Charters Adventures Worldwide

Leeward Antilles

Now we’re far south, where the sun is hot and the beer is dutch! The Leeward Antilles are the ultimate in chilled Caribbean escapes. Sitting just north of the Venezuelan coast, islands offer some great protected sailing. These islands are steeped in history, and treks ashore to explore abandoned Dutch forts essential – just not in the midday heat. Bonaire is the local home to sailing – with a compass in its flag, how could it not be?! The island is host to one of the Caribbean’s oldest regattas and attracts entrants from all over the world for their famous relaxed racing and great socials ashore.

Primary sailing locations

Aruba, Curaçao, Bonaire

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