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Caribbean adventure sailing holiday: Antigua – St Lucia

Caribbean adventure sailing holiday: Antigua – St Lucia

Coastal Sailing

No previous experience required


Come and join the crew on this wonderful sailing adventure as we sail and explore the Windward Islands of the Caribbean between St Lucia and Antigua. In between these two iconic islands, we also have Martinique, Dominica and Guadeloupe to be discovered. The warm trade winds give guaranteed great sailing and our schedule allows plenty of time to pick and choose which of these islands we explore en route. Get ready for jungle wreathed mountains, coral reefs, turtles, white sun-soaked beaches, fascinating towns and - of course - sailing as good as it gets!

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This is a sample itinerary for the route between the Caribbean islands of St Lucia and Antigua. if you are sailing from Antigua to St Lucia, please just reverse it! The wind and weather dictate exactly what happens and when on these adventures (that’s what makes them so special – there is no fixed itinerary). We may visit all the islands mentioned or we may miss one out to give us more time to explore elsewhere. You the crew will be making the plans!

Day 1: Joining the boat

Join the boat between 1200 and 2000hrs (the closer to 1200 the better but we know flights and such like don’t always work like that, so don’t worry!) Get your belongings packed away and relax. There’s plenty of things to do in the future, but right now it’s about relaxing, finding your way around the boat and enjoying the surroundings.

Day 2: Initial training and getting out sailing

Today is all about getting up to speed with the boat. Whether you are a complete novice and learning to sail for the first time or a more experienced sailor, everyone benefits from detailed introductions, safety briefings and training sessions. You will have two highly qualified instructors to guide you through every aspect that you need to know to have a great sailing holiday.

By lunchtime, we should be casting off the lines, and it’s time to learn the ropes. You’ll be hoisting the sails and working through all the critical sailing manoeuvres such as tacking and gybing, reefing and knot tying! By the end of the day, everyone on board should feel comfortable with the basics – even though there’s more to learn and practice every day. We’ll find a wonderful spot to anchor for the night and have dinner and a beer under the stars and in the warm, spice-laden Caribbean air. This holiday has most definitely started!

Days 3-5: Sail to and explore Martinique

It’s a perfect length sail today as we head north to the French Caribbean territory of Martinique. 30nm north of St Lucia, it gives us a really fun first passage and you will get a real feel for just how special these expedition yachts are in the trade winds. Now we are in the footsteps of history, following routes plied by men such as Drake and Hemmingway and there is always a visceral thrill as we approach the shores of a new island.

Martinique has been tied to France since 1635 and is a spectacular island of tropical forests, wonderful beaches and towering volcanoes. Its colonial history is still everywhere to be seen, and there are gardens and plantations to wander through. Yet this much-loved island remains exuberantly Caribbean. Shops stack tempting pâtés créoles and windows are laden with wildly coloured fabrics. the streets are regaled with the rhythms of beguine and zouk, and everywhere is the smell of in spices, breadfruit, coconuts and the local delicacy: a small, sweet banana known as figue pomme.

Maybe we’ll get to Anse du Ceron, on the north-west coast. Think perfect beach, snorkelling and for the adventurous, a swim out to Ilet la Perle, or Pearl Island, and the chance to play and dive off its rugged rock formations.

Days 6-9: Sail to and explore Dominica

It’s time to set sail again and another passage that sums up why Caribbean sailing is just so good. There are adventure holidays and then are real adventures like this one! We have about 25nm of open water to cross, which allows our yacht really to fill her sails, stretch her legs and charge across to Dominica.

We’ll likely make landfall on the south-west coast, in the capital Rouseau. The town is so much fun to visit and flanked by the Roseau River and Morne Bruce, giving spectacular views out over the Caribbean Sea. It is also rich in local history, having been built on the site of the ancient Kalinago Indian village of Sairi.

Dominica has so much to see and do, we may well spend 2-3 days here. There’s the absolute must of snorkelling or diving on the world-famous Champagne Reef, named due to the bubbling waters rising from volcanic thermal springs on the ocean floor. The reef’s vast cliffs and volcanic formations are incredible to see.

We also have to take a tour up the Indian River, named after the Kalinago Indians who lived along its banks and rowed down it to get to the Caribbean Sea. The river was a key trading and transport route for them. Its shores are the most wonderful wetlands, with amazing Bwa Mang trees showing the route. We can hire some local guides to take us along the river.

Days 10-13: Sail to and explore Guadeloupe

Hard though it is to say goodbye to Dominica, our sailing holiday continues with the gorgeous French Caribbean island of Guadeloupe some 30nm north of us, and so it’s another glorious sail back out on the sea. If we leave after breakfast, we will make landfall after lunch and in the hot sun will be pulling into Pointe à Pitre.

Very much the heart of the island, Pointe a Pitre is the most lovely place to wander around and explore. Right in the centre, there’s the Marché de la Darse, where local fishermen sell their catch directly from their boats and the grassy Place de la Victoire square is surrounded by cafes and old colonial-era buildings. If we get here in good time, we may even be able to head off for a visit to the Cascade aux Ecrevisses, a stunning jungle-fringed waterfall where we can swim.

Next, we must sail to the small island of Marie Galante, famous for its perfect white sand beaches, fascinating buildings and very (very!) relaxed vibe. It’s then just a short sail to the fascinating, knock-out the Archipelago of Les Saintes. Only two of these nine small islands are inhabited and they are regularly voted some of the Caribbean’s most beautiful and undeveloped bays.

Day 14: Sail to Antigua

Agonisingly, our sailing holiday is drawing to close and the adventure concludes with one last sail to the ever-brilliant island of Antigua. It’s around 40nm, so we’ll be out at sea for five to six hours, breathing in the salty air one last time, charging north through the waves and then it’s mainsail down, headsails away and we’re pulling into (probably) English Harbour, with its famous Napoleonic era forts, bars, restaurants, beaches and everything else we need to have a very special last night out as a crew, celebrating the best sailing you could ever have, true exploring and bucket loads of adventure.

Day 15: Pack up and goodbyes

That’s it. The holiday is at an end, and all that remains is to pack away our holidays, fill our bags with any momentoes we have picked up along the way, sign logbooks and exchange details with the rest of the crew. Many crew members join these adventures solo, but with the friends you meet and share the experiences with, time and time again we see everyone heading off on new adventures together and that is all part of the magic.


  • You should join the boat in Rodney Bay, St Lucia or English Harbour, Antigua after 1200 hrs on the first day. It is good if you can join us as close to 1200 hrs as possible, but if your flight or ferry gets in later than this, that is fine. We will ask you closer to the time to let us know your travel details.
  • You will disembark the boat in Rodney Bay, St Lucia or English Harbour, Antigua between 0900 and 1200hrs.


  • St Lucia has two airports. Hewanorra International Airport (IATA code: UVF) is the main international airport but you can also fly into Castries (IATA code: SLU).
  • Sometimes, it can be much cheaper to fly in/out of Martinique and Guadeloupe, the neighbouring islands to St Lucia and Antigua. As they are French territories, the airfares can be heavily subsidised and there is a quick, easy ferry from them to St Lucia and Antigua



These adventure sailing holidays are open to everyone aged 18 years and over. If you are aged 70 or over, or have any concerns about your health, we ask that you get a doctor’s note before booking. This is just to make as certain as possible that you will be okay out on the water.



We provide the foul weather clothing, life-jackets and all other technical equipment you will need. We really urge you not to spend any extra money unless you are sure you want to! You need to bring a sleeping bag and some waterproof boots.

See more information and the full kit list here


We are committed to helping as many people as possible have an amazing sailing holiday and experience the magic of the sea. Our skippers and mates have medical training and the boats have some medical supplies and equipment on board. However, the reality is that once on board access to professional medical assistance is going to be slower than if you were on land. If we are offshore it may be some days. For this reason we ask you to check through the medical disclosure form below before you book. If you answer yes to any of the questions, you should get in touch with us before you book. It will probably still be fine but it’s good to make sure. You will be asked to submit the form electronically 14 days before the start date, ensuring that we have the most up to date information.

See the Medical Declaration here


  • It is essential that you have adequate travel insurance in place for your sailing holiday.
  • We strongly recommend that you arrange insurance that covers you for any medical mishaps in the build up to your holiday so that should you have to cancel, you can reclaim your fees.
  • Please note we cannot refund your money or cancel your invoice due to medical issues.
  • For our latest guidance on travel insurance, please read here.


Mostly day sailing, shorter mileage and more time to head ashore and explore.


  • Foul weather clothing to keep you dry in any conditions.
  • Fladen immersion suits. These will keep you warm in even the coldest, windiest conditions.
  • Ocean-spec lifejackets. These are the best on the market.
  • All on-board food and snacks.
  • Daily sailing lessons and tuition from two highly experienced instructors.
  • RYA sailing qualifications where applicable.


  • Your travel to and from the start and end points.
  • Travel insurance (see our travel insurance page here)
  • Any alcohol – but feel free to bring your own or buy some along the route.
  • Any meals you eat ashore.


Everything’s included except for flights, travel insurance, a sleeping bag and some waterproof boots. There are no hidden extras.

  • These expeditions have small numbers of people on board. When you book, you are committing to being a part of the crew.
  • These are genuine adventure sailing holidays and you will be helping sail the boat, planning where we go, navigating, cooking and keeping the boat clean and tidy.
  • When you book, the deposit is non-refundable. It is possible to cancel subsequently, however you may still be liable for the balance of the invoice, depending on how close you are to the start date when you cancel.
  • Please ensure you have read and agreed to the T&Cs and read the Trip Notes before booking.

    Terms & Conditions