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Caribbean adventure sailing holiday: Leeward Islands

Caribbean adventure sailing holiday: Leeward Islands

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 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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Route Map Image

These are the available dates and routes. To book your place, please select the dates from the drop-down above the ‘Add to Cart’ button.


  • Start date / place: January 30 2022. Rodney Bay, St Lucia
  • End date / place: February 10 2023. Rodney Bay, St Lucia
  • Full price: £2,099
  • Deposit: £525


  • Start date / place: February 13 2023. Rodney Bay, St Lucia
  • End date / place: February 24 2023. Rodney Bay, St Lucia
  • Full price: £2,099
  • Deposit: £525


Please see ‘TRAVEL – GETTING TO & FROM YOUR TRIP’ tab for advice on start and end points.



This is non-refundable. On making payment, your berth is guaranteed.

Paying the balance
The balance of the invoice can be paid at any time. It must be received by Rubicon 3 90 days before the trip start date or your place will automatically be cancelled. We will remind you of the date nearer the time.

Cancellations and moving trips
Our expedition sailing yachts only have between 7 and 10 berths on them. When you book, you are committing to take one of these places. Due to these very limited numbers, we will often have turned away someone else who would have liked the berth. Unlike many other holidays, please understand this gives us little if any flexibility to make changes or to move trips. We will always endeavour to assist you (& the earlier you tell us the better), but unless we can find someone else to take your place, we usually cannot move your booking.


This is a sample itinerary for the route between the Caribbean islands of St Lucia and Antigua. 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!

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!

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.

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.

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.

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.

Passage back to St Lucia

having explored these wonderful islands, we have one last exhilarating sail back to St Lucia. It’s 180nm, so it will be a full 24 hours and we will be charging along, passing by all the wonderful places we have explored on the trip. As we sail through the night, it is also a hugely fun opportunity to sail under the stars in the warm Caribbean winds.

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 at 0900 hrs on the first day.
  • You will disembark the boat in English Harbour, Antigua between at 1200hrs on the last day.


  • 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. You need to bring a sleeping bag and some waterproof boots.

See more information and the full kit list here


We believe that as many people as possible should be able to head out to sea and have a great adventure. However, it is essential for everyone’s safety that you are in a fit enough state to be on board. Ability to complete the five exercises below is a pre-requisite for joining as a crew member. They are not designed to be physically taxing and almost everyone should be able to complete them. Rather they are in place to check that you have the stability and basic physical condition to be on-board. If when you join the vessel the skipper believes you are not capable of completing these exercises, you will probably not be allowed to embark. If you have any doubts at all about your ability to complete these exercises safely, you must contact your doctor before attempting them.

Fitness to sail


Four weeks before your trip start date, you will be sent final joining instructions. At this time you will be asked to complete our medical declaration. At the time of booking, it is your responsibility to be sure that you will be able to pass all the criteria at the start date of your trip. If you cannot pass the criteria you will probably be refused permission to board.

See the Medical Declaration here


  • All crew must have adequate travel insurance in place for your sailing holiday.
  • We strongly recommend that you arrange insurance as soon as you book. This ideally will cover you for any mishaps, medical or otherwise, in the build-up to your holiday so that should you have to cancel, you can reclaim your fees.
  • Please note we will not refund your money or cancel your invoice due to medical issues that disqualify you from joining your trip.
  • For our latest guidance on travel insurance, please read here.


For a full explanation of what to expect with the various trip ratings please click here.


  • 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