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Caribbean Sailing Holidays: Rubicon 3’s guide Articles

Caribbean Sailing Holidays: Rubicon 3’s guide

Long-time Caribbean cruiser Bernard Toussaint tells us why it’s one of the world’s best cruising grounds

Bernard Toussaint: July 21 2022

“A turtle just swam by the boat!” came the call from the deck, and there it was. Despite the lush green volcanic mountain, the white sandy beach glistening in the sun, and the perfectly turquoise water, the highlight of the vista was still this fabulous turtle. People ask me what is most notable about the Caribbean – but there is no one thing. Everyone knows about the sun, sea and sand, but there is a vibe here – a uniqueness hard to define – that is its true quality.

I saw that turtle in 1988 when I first sailed to the Caribbean. I was anchored in the Tobago Cays, worried about money and life issues, but all was forgotten in an instant. The beauty of it transfixed me. As the turtle vanished, I wanted to explore with it, and I sensed then that I wouldn’t be returning to France for a long time. In the many years since, I have wandered and explored these islands, watching them change yearly. They are majestical, beautiful and unique – and for those who would like to follow in my footsteps, this is my humble guide to just some of my favourite places.

Caribbean SailingThe layout of the islands

Lucayan Archipelago

First, you must understand the layout of the islands because they are distinct regions. At the northern extreme is the Lucayan Archipelago, which you will know as the Bahamas and the Turks and Caicos. No question for me – the real highlight of the Bahamas is the swimming pigs in the Exuma district. Found around 80 miles southeast of Nassau, the area is entirely uninhabited by humans – yet these pigs swim through the water and are hugely inquisitive. I laughed out loud from pure wonder when I first saw them, and if you ever get the chance, you have to see them. If you are passing through the T&Cs, as they are universally known, you must try to get to Salt Cay, one of the few places in the world where you can get in the water and snorkel with the humpback whales. Salt Cay is considered ‘Whale Central’ from January to March each year, and seeing one of these fantastic creatures in the water is the thrill of a lifetime.

The Lesser Antilles

The Greater Antilles encompassing Cuba and Puerto Rico are just below the Lucayan Archipelago. By the way, the Lesser and Greater Antilles (which include the British Virgin Islands at their eastern edge) and the Lucayan Archipelago are collectively known as the West Indies. Here I will describe some highlights of the Lesser Antilles and the islands that most of you will associate with the Caribbean. Here we have the Leeward and Windward Antilles, and below them, the Leeward Antilles.

The Leeward Islands

There are 15 islands in this grouping, of which the most famous are St Martin, St Barts and Antigua. For hundreds of years, they have been crucial to explorers and traders, and I have always loved their white-sand beaches, shady palms and turquoise waters. I particularly love the wildlife here, and the Frigate birds always seem to take a shine to my ketch, Sirène. Barbuda has a wonderful sanctuary for them that you can visit.

Little Bay

Keeping to the theme of nature’s beauty, for me, Little Bay in Anguilla is genuinely perfect, even by Caribbean standards. 20-metre cliffs, coloured in rich reds and pinks, and full of grottos and caves, soar up from the sea. You will see more of my beloved wildlife, including tropic birds, pelicans and kingfishers.

Anse de Colombier

One thing that has changed in my 30 years here is the number of people. I love it, and meeting the itinerant sailors passing through, with their hopes, plans and stories, is a real passion of mine. But sometimes, like all sailors, I need to be alone. This is when I head to Indian Creek on Antigua. I can’t say it’s the most visually beautiful, but it’s so secluded, and as if you are on the set of a cowboy film (maybe why it’s called this?) and for that, it is perfect. For many years I have overnighted in Anse de Colombier of St Barths. Very difficult to reach by land, it was always my treasure island (as is Rendevouz beach off Antigua). The last time I was there, however, a terrible super yacht took over the bay, blocked my vista, and I left, promising never to return. But I surely will, as it’s still magical!


Being French, naturally, this is a favourite destination of mine. I can sit by the Cathédrale de St-Pierre et St-Paul, eating croissants from the boulangerie, drinking proper cafe and almost imagine I am back in my childhood, sitting with maman in the cafes by the Seine. I love Basse-Terre, which has Guadeloupe’s more dramatic, mountainous side. The Parc National de la Guadeloupe mountains fill the island’s centre. It has a wonderfully thick tropical jungle, with huge waterfalls and thousands of birds to discover, all keeping cool in the foliage. I come here to hike, but I will also swim and dive off the gold and black sand beaches. Of course, you must also hike up to the summit of the La Soufriere volcano. It is nearly a mile above sea level, and let’s be honest, it’s often quite stinky, but as the clouds clear, it’s a lovely place to be, and many of my friends will stop at the Bains Jaunes thermal pool after the climb.


I have great friends who live here, so I am a regular visitor, and it has become a true love of mine. This island is all the more remarkable because it is less visited. You must take a canoe and paddle up the Indian River, where the giant swamp bloodwood trees overhang the water. Also, here we have the reefs, wetlands and rainforests that form the Cabrits National Park. It is not sensible to head off alone, so hire a guide to help you explore the beautiful rainforest, and for sure, you will see why this is a Unesco World Heritage Site. Early in the morning, I love to be at Chaudiere Pool, which is fed by waterfalls and overlooks the cliffs, the sea, and the coral reefs.

The Grenadines

Now we are down south in the Windwards, where we can cruise the islands between St Lucia and Grenada. You must visit Bequia, maybe the most beautiful of them all. I met my wife Hélène here, so perhaps that is why it is close to my heart. You may have guessed I am not much the one for the prominent Hollywood actors and celebrities, but Mustique, with all its luxury and super yachts, is where they come. I met David Bowie here back in the late 1980s, but I did not know it. Helene told me afterwards. I had wondered why she was so distracted. I adore his music, so maybe I should have known. Of course, you must swim at the Tobago Cays, south of St Vincent. You will probably see turtles and the perfect water and sand that first captured my heart. Maybe you will be like me and wander these islands for years after. Finally, right down south, you will find Grenada, where Hélène and I now live. So if you see me, say hello!

Caribbean Sailing: how to do it with Rubicon 3

Caribbean Islands

A mixture of offshore and coastal sailing

Rubicon 3 have a great combination of destinations for our Caribbean sailing season, with short coastal sails and longer, open water voyages. This means that there is something for everyone. There are the short coastal explorations of our Grenadines trips or our incredible journey between St Lucia and Antigua, which takes in Montserrat, Dominica and Guadeloupe along the way. Another massive favourite with perhaps the most beautiful beaches is our British Virgin Islands holiday.

For those who like to head offshore in the warm trade winds, you can sail with us from Antigua to Jamaica or even from Jamaica up to New York City. The duration of most trips is 12 days.

Caribbean offshore sailing

Beaches, swimming and exploring ashore

Except on the offshore routes, we will stop somewhere new every day. The Caribbean is home to some of the world’s most beautiful water and beaches, and you will have plenty of time during your holiday to swim, soak up the sun on the white sand, explore ashore in the town and probably fit in some jungle trips too.

Clear blue waters of the Caribbean

The food

You have three meals a day on board, but it’s lovely also to sample the local food and restaurants, of which there are so many great ones. Each island’s mixture of different cultures and cooking styles means a rich array of delicious food on offer. A personal favourite of our skippers is the green fig and saltfish you find in St Lucia, although the fig, in this case, means unripe banana. We’d also recommend Callaloo, a Dominican stew dish, the fusion food of Martinique, which is a mixture of African, French and Creole cuisine.

Caribbean Food


The Caribbean sits in the north easterly trade winds, so it is guaranteed to have good wind every day, making it such a special place for sailors. The average temperature when we are there (January to March) is around 28° C, with the sea only a little less at around 23°C. Nights are slightly cooler at about 22°C, but they never get cold. You can expect one or two intense but short-lived showers once or twice a day

Sunny beach - Grenada


Here at Rubicon 3 we are explorers, but it’s hard not to love a fun race now and again. We enter the best three events each year: the Grenada Sailing Week, the RORC 600 in Antigua and the St Maarten Regatta. They are all around a week long, and our entire focus is on learning and having fun. We hate the shouting and aggressive side that comes with some racers, and you’ll never see it with us.

Caribbean sailing. Why do it with Rubicon 3?

Caribbean sailing holidays come in all different shapes of sizes, including day charters, week charters, 2-week charters, bareboat charters, flotilla holidays and racing. We are unique because we sail from one part of the Caribbean to another on most of our trips. So you might start in St Lucia but end up in Antigua. It gives that real sense of travel and adventure that you will never get on a Sunsail holiday. You can join solo (most do), and no prior experience is needed, with your skipper and mate giving you top-level instruction. So whether you want to try an exciting week of racing or have the perfect sailing holiday, there’s a reason Rubicon 3 are Europe’s #1 sailing adventure holiday.

Sailing yacht

Who we are

Blueco Holdings Ltd, t/a Rubicon 3 Adventure
20 – 22 Wenlock Road, London, N1 7GU

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