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Looking For Sailing Vacations in the Caribbean? Articles

Looking For Sailing Vacations in the Caribbean?

It’s Paradise on the Water!

Imagine yourself sailing through turquoise waters, surrounded by picturesque islands, and basking in the warm Caribbean sun. Sounds like a dream, right? Well, turn that dream into a reality with an adventure sailing holiday in the Caribbean run by Rubicon 3, rated sailing’s #1 adventure sailing company. Our routes offer a perfect blend of adventure, relaxation, learning about sailing and unforgettable experiences and the tropical paradise that is the Caribbean is just waiting for you to come and have one of the most exciting sailing vacations you could imagine.

The Rubicon 3 ethos means that whether you’re a seasoned sailor or a complete beginner, you’re very welcome to join us. Our skippers are famous for the friendly, supportive atmosphere on board and they’ll teach you everything you need to know to be fully involved from day one. These adventures are also perfect if you’re travelling solo, as our bookings are on a single berth basis and over 90% of our crew join solo too.

Here we’ll guide you through the various routes we run, the different types of sailing holidays in the Caribbean, and the top activities you can enjoy during your adventure with us. So dive in and we’ll help you discover paradise on the water!

offshore sailing caribbean


What you’ll find in this article

  • The magic of the Caribbean islands
  • Discover stunning beaches, crystal-clear waters and diverse activities in British Virgin Islands, Windward & Leeward Islands.
  • Customize your itinerary and explore coral reefs, hot springs & more, plan ahead for an unforgettable experience!

Discover the Caribbean Islands

pitons st lucia


The Caribbean is a true paradise for sailors, offering picturesque beaches, crystal-clear waters, magical coral reef and a wealth of things to do beyond sailing once we’ve docked or anchored for the day. Our Caribbean cruising ground covers by far the largest area of any company, with our focus being on sailing from one island to another, not just starting and finishing in a base, such as Sunsail or Moorings do. That means with Rubicon 3, it’s not just a great vacation but a real adventure. Our Caribbean cruising area covers the Windward Islands from Grenada up to St Lucia, the Leeward Isles from St Lucia up to the British Virgin Islands, and then right on up to the Bahamas. Our Caribbean season starts in late December, after we have crossed the Atlantic with the ARC and ends in about May, when we head north to the USA, Nova Scotia, Newfoundland, Greenland and beyond.

But back to the Caribbean, where each island group has a unique charm and attraction, meaning you can really pick the adventure sailing holiday that best fits you. Right – time to dive in and explore in a bit more detail the main island groups and the trips we run.

The Windward Islands

Sailing in the Windward Islands is an extraordinary experience that offers a unique blend of natural beauty and cultural richness. These islands start in the south with Grenada, and then you are into the Grenadines and St. Vincent before topping out at St Lucia. It’s a chain of islands that boasts a magical combination of stunning landscapes, vibrant marine life, and welcoming local communities.

Sailing in the Windward Islands means short distances and a new destination each day. In fact, of all our sailing vacations, the Windward Islands is our most ‘holiday style’ of all. The reliable trade winds make for guaranteed great sailing in the turquoise waters, the distances are short and the water mostly sheltered. The islands themselves are quite diverse with a mix of lush rainforests, dramatic volcanic peaks, and hidden coves. It adds a big element of adventure and exploration to every trip.

One of the highlights of sailing in the Windward Islands is the many stunning and secluded anchorages, just off pristine beaches. The UNESCO world nature reserve of the Tobago Cays will also be one of the absolute highlights, being a stunningly beautiful placer where you can can swim with turtles and experience a truly unique part of the world.

Sunny beach - Grenada

Beyond their natural wonders, the Windward Islands are rich in culture and history. Grenada, known as the “Spice Isle,” is a vibrant mix of African, French, British, and West Indian influences. Indeed, the Grenadian culture is deeply rooted in its agricultural heritage, with nutmeg, cinnamon, and other spices playing a significant role in the local cuisine and traditions.

St. Vincent, often referred to as the “Mainland,” has a particularly diverse cultural tapestry influenced by its indigenous Carib population, African heritage, and colonial history. The Garifuna people, descendants of West African slaves and Caribs, still have a strong presence on the island and it’s fascinating to discover their unique language, music, and traditions.

St. Lucia is renowned for its dramatic landscapes including the world famous Pitons. It has a captivating cultural blend of African, French, and British influences. Its culture is deeply rooted in storytelling and folklore, with traditional dances like the Kwadril and the Jounen Kwéyòl celebration.

So whether you’re a seasoned sailor or a novice adventurer, sailing in the Windward Islands is magical, with breathtaking landscapes, perfect wind, secluded anchorages, and vibrant local cultures. It all combines to create a very special sailing adventure.

See Rubicon 3’s Windward Islands adventure sailing holidays here

Leeward Islands

The Leeward Islands, are just to the north of the Windward Islands, and run from St Lucia up to the British Virgin Islands.

Sailing in the Leeward Islands of the Caribbean is a truly special experience, offering a unique blend of stunning landscapes, crystal-clear waters, rich cultural heritage, and warm hospitality. Let’s explore some of the notable islands in the region and what makes them so remarkable for sailing enthusiasts:

Martinique is just north of St Lucia and is known as the “Island of Flowers”. It is a French overseas territory that perfectly blends Caribbean and French cultures. Its rugged coastline is dotted with picturesque bays, including Anse Mitan and Grande Anse d’Arlet. The island’s verdant rainforests, Mount Pelée volcano, and charming coastal villages like Sainte-Anne all add to its magic.

Antigua from our Caribbean sailing holiday

Dominica is often referred to as the “Nature Island.” Its dramatic landscapes feature pristine rainforests, cascading waterfalls, and volcanic peaks. The protected anchorage of Prince Rupert Bay in Portsmouth is our starting point for exploring the island with glorious attractions including the Boiling Lake, Trafalgar Falls, and the Indian River. Less known to man, Dominica is a mega star of the Rubicon 3 itinerary

Guadeloupe is actually made up of several islands, including Basse-Terre and Grande-Terre. It is most famous for the magnificent La Soufrière volcano while the nearby Îles des Saintes, a small archipelago with crystal-clear waters and charming fishing villages, is a favourite stop Rubicon 3

Antigua is appropriately known as the “Land of 365 Beaches,” with one for every day of the year. It is perhaps the epicentre of Caribbean sailing and host to the RORC Caribbean 600 in which we love to compete.

St. Kitts and Nevis is a two-island nation that combines natural beauty with a rich history. St. Kitts features a well-preserved colonial architecture and the UNESCO World Heritage Site of Brimstone Hill Fortress, offering panoramic views of the Caribbean Sea. Nevis, its smaller sister island, is known for its rainforests, volcanic peaks, and charming plantation inns

St. Maarten/St. Martin is a unique island as it is shared between two nations, the Netherlands and France. The dual heritage has created an intriguing blend of cultures, cuisines, and languages.

These are just a few examples of the Leeward Islands’ allure for sailing enthusiasts. Each island has its own distinct charm, but they all share a common thread of natural beauty, warm hospitality, and a welcoming environment for those seeking unforgettable sailing adventures in the Caribbean.

Our routes exploring the Leeward islands are slightly more adventurous and off the beaten track and magical for it.

See our Leeward Island sailing vacations here


Types of Caribbean Sailing Holidays with Rubicon 3


A Caribbean sailing holiday can vary hugely depending on where you go and what you are looking for. It may be you are looking to get away as a family, with lots of beaches and exploring ashore or you may be looking for a big offshore adventure or something in between where you combine wonderful sailing but with fascinating places to discover ashore. Rubicon 3 offers something for everyone, ensuring that your time in the Caribbean is nothing short of extraordinary.

Let’s delve deeper into the different types of sailing vacations we offer.


Solo Traveller Getaways


sailor girl

For those travelling solo, our Caribbean adventures are perfect. Over 90% of our crew join solo so you have none of that awkwardness of having to fit in with another group. The boats are fun, relaxed and so friendly, so you are in for an unforgettable experience.

As well as the sailing, our coastal Caribbean adventures are island hopping, ensuring you can explore as a group or head off solo for a while to discover secluded beaches, hidden coves, and enchanting islands at your own pace. With the Caribbean’s stunning scenery and endless opportunities for adventure, a solo sailing holiday here works just about perfectly.

Family-Friendly Sailing

A family-friendly sailing holiday is a perfect way to spend quality time with your loved ones while exploring the Caribbean’s breathtaking beauty. With 9 berths on a yacht, we can accommodate the whole family or two families on a private charter (you’ll need to book well in advance) or you can join one of our standard schedules. We can accommodate children of 16 or over (on private charters this age range can be lower) and with the days filled with learning to sail, swimming in warm waters, snorkelling, going on RIB rides, playing on the beach and exploring ashore, a Rubicon 3 Caribbean adventure will create unforgettable memories for your family.


Happy sailors


Adventure-Seeking Enthusiasts

For those who crave some adrenaline-fueled experiences, look no further. It might be that you want to experience the huge thrill of sailing hundreds of miles offshore in the warm sun and strong trade winds. For others, it will be anchoring off secluded coves in places such as Dominica and hiking up to the Boiling Lake or kayaking down the Indian River! There is diving and snorkelling, wrecks to be discovered, cultures to explore and thrills a minute. For maximum adrenalin, you could even sign up for some of the Caribbean race season and compete against other yachts as we speed around the islands. It is utterly exhilarating!

swimming pigs sailing adventure bahamas

Caribbean Racing

Caribbean yacht racing is thrilling and a real highlight of our winter season. We take part in Grenada Sailing Week, which is short races around the island of Grenada and is super relaxed, maximum fun and a huge win every year. We also enter the RORC Caribbean 600, the iconic 600 mile offshore race starting and ending in Antigua and weaving its way through the northern isles. Our final race is the St Maarten Heineken Regatta, which is all glitz, glamour and spectacular parties ashore after each day’s sailing. With turquoise waters, consistent trade winds, and a deeply ingrained sailing culture, the Caribbean races are exhilarating.

Caribbean sailing

Those new to racing are absolutely welcome to join – encouraged even – as we know it can be a daunting first step. So we are here to teach you and help you learn in a super gentle and relaxed environment. We race hard but we also don’t get hung up on where we finish. It’s about having fun. Those joining the RPORC 600 should have race experience or good offshore experience.

Offshore Sailing in The Caribbean

Sailing offshore from the Leeward Islands to islands such as the Dominican Republic or the Bahamas make for exhilarating blue water passages across the Caribbean Sea. You’ll soon be hundreds of miles offshore, charging along downwind powered by the strong trade winds and favorable currents. The passages range between 600 and 1000 nautical miles, providing a real mix of challenges and rewards. As the sun sets each day, the night sky lights up with a breathtaking display of stars, creating a magical but still warm atmosphere. Sunrises are equally breathtaking. The anticipation is always huge as our chosen landfall comes into view with verdant green landscapes and palm-fringed beaches, signalling a successful voyage and the opportunity to explore a new island, new culture, historical sites, and a very well-earned post-voyage party!

Yacht bluejay under sail

Sailing Seasons and Weather Conditions

The best time to embark on a sailing holiday in the west indies is during the region’s dry season from November to April, and no surprise this is when we are there, arriving from Europe in early to mid December until we set off for the USA in April. This period offers ideal sailing conditions, with steady northeast trade winds, warm temperatures, and minimal rainfall, ensuring a perfect sailing environment. Most days we can get a small rain shower but that clears the air and you’ll soon appreciate it! Expect a day time average temperature of around 27°C (81° F) dropping to around 20°C (68° F) at night.

But never fear – Rubicon 3 yachts have air conditioning and wind scoops to help keep a pleasant temperature below decks!

Sailing holidays for solo travellers


Tips for a Memorable Caribbean Sailing Vacation With Rubicon 3

To ensure a memorable Caribbean sailing vacation, first make sure you’ve picked the right trip for you. If you’re not sure, we are the experts so just pick up the phone and speak to us on +44(0)20 3086 7245 or email us at infor@rubicon3adventure.com and we’ll work with you to pick the perfect trip.

We have a packing list, which is adjusted for each region, so that will let you know what to pack and what you do or don’t need.

Caribbean turtle

Don’t feel you need to work out all the connecting flights yourself. We know the routes really well, so tell us where you’re coming from and we’ll help you pick the right flight. Finally, once you’re signed on, you can join our crew Facebook page and that will enable you to connect with other crew on the same trip and plan to meet up, share taxis or whatever it is that will help.


Embarking on a Caribbean sailing holiday truly is an experience like no other, offering a perfect blend of adventure, relaxation, and unforgettable memories. From exploring the breathtaking beauty of the Windward Islands or Leeward Islands to a huge offshore adventure or inter island racing, there’s a Caribbean sailing vacation for everyone.

So, what are you waiting for? Get a place on board, feel the warm Caribbean breeze, see those spectacular sites and set out on your very own Caribbean paradise adventure on the water. The Caribbean is calling!


Frequently Asked Questions

Do I need any experience?

For most of our Caribbean sailing vacations, absolutely not. Indeed the Leeward Islands and Windward islands routes are brilliant ways to start sailing. You’ll learn everything you need to know about the boat, learn about boat handling, sail trim and how to drop anchor and enjoy some stunning scenery while you learn.

Can I join solo?

Absolutely you can. In fact 90% + of our crew join solo, so it makes for a brilliant holiday if you are coming alone, with none of the usual worries about single supplements, being the only solo traveller or not having other people around. You will bind with the other crew so quickly and very likely make some friends for life.

Who else joins and what age?

It’s a really eclectic mix, with usually a 50:50 male to female ratio and an age range of 30-75. So long as you have decent agility, balance and day to day fitness, age is not a concern for us. A number of people have no prior experience, with about half having done some sailing in the past but feeling as though they have forgotten most of it. We’re here to teach you so don’t worry about that!

Who we are

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

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