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Caribbean adventure sailing holiday: St Lucia to Jamaica

Caribbean adventure sailing holiday: St Lucia to Jamaica

Offshore & ocean sailing



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An incredible trade wind sailing holiday from St Lucia to Jamaica.

Join the boat in the wonderful island of St Lucia with its volcanoes and beaches. We have a few days to cruise and explore the island before we set off on a 900nm downwind sail to the east coast of Jamaica. The Clipper 60s were built for exactly this and is hard to think of a more exhilarating or wonderful ocean sail. Being downwind, the boat will be pretty flat and speeding through the water at close to 10 knots 24 hours a day. Wonderful warm sun in the day and incredible Caribbean star scapes at night will mean this is an experience that stays with you for life.


Sailing location 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: March 27 2023. Rodney Bay, St Lucia
  • End date / place: April 07 2923 2022. Port Antonio, Jamaica
  • Full price: £2,159
  • Deposit: £540


This is an entirely optional day prior to the start of the trip where we train you in the navigational and passage planning skills needed for an ocean passage.

Find out more about the day here.

If you wish to attend the Ocean Theory Training Day (please ensure you add the module to your basket), you will need to join the boat at 1000hrs the day before the main start date. You will be allowed to stay on the boat that night


  • This trip meets the RYA Yachtmaster Ocean for a qualifying passage, so long as you are a watch leader.
  • If you wish to join as a watch leader, you must meet the criteria as detailed on our ‘Watch Leader‘  page.
  • It is also compulsory to attend the ‘Ocean Training Day’ which gives you in depth training on how to run an ocean passage.
  • You must book the watch leader place at the same time as you make your main booking. Please ensure you have added a ‘watch leader’ module to your cart.
  • There are only three watch leaders spaces per yacht.



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 typical itinerary. What makes an adventure holiday so special however is that there can be no fixed itinerary and no part of this is guaranteed. The wind and the weather ultimately shape what’s possible each day but everything is very flexible within that.

Joining day

Join the boat at 0900hrs. 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. Martinique is famous in the Caribbean for its wonderful beaches, fun bars and beautiful towns and anchorages.

Training and exploring on the coast of St Lucia

Today is all about getting up to speed with the boat. Whether you are a complete novice or more experienced sailor, everyone benefits from detailed introductions, safety briefings and training sessions. You will have two highly experienced instructors 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, hoisting the sails and working through all the key 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 mayanchor for the night  in one of Martinique’s most beautiful locations. Petit Anse D’Arlet. On the way, we’ll sail past Diamond Rock, a rock formation that resembles the shape of a sunken warship. The English Navy named the rock formation HMS Diamond Rock during the Napoleonic wars. Petit Anse D’Arlet is an ideal place to anchor, swim and snorkel for the evening, while also exploring the French Caribbean town and its delicious speciality Creole cuisine.

Preparation and planning for the ocean passage.

With five days of open ocean sailing ahead of us, we’ll be making detailed passage plans, preparations and victualling the boat with all sorts of lovely food and meals from the Caribbean. It’s fantastic training for everyone and we’ll be checking sails and all the other equipment needed for this type of voyage. It’s always a very exciting time and we’ll need lots of cool drinks and shade as we work through the day getting ready.

Across the Caribbean Sea to Jamaica!

It’s time to cast off the lines and head west for Jamaica. We have around 980nm to go, so we can expect to be at sea for the next five days and nights although, of course, the actual time needed will depend entirely on the weather. You will quickly settle into a 24-hour watch system and the general rhythm of life at sea. Days will be filled with navigating, helming and trimming sails, galley duty and cooking up a hearty meal for the crew. There’s celestial navigation to be tried and there’s still plenty of time just to gaze out over the warm waters of the Caribbean and muse! Depending on our route you may well see the Dominican Republic and Haiti on our starboard horizon. Sailing at night in the Caribbean can be one of the most exhilarating and memorable things you will do. After our voyage from St Lucia, it’s time to head to the beach, swim in the wonderful sea and relax on a Jamaican beach. There is wonderful snorkelling here and all sorts of wildlife.

Debriefs, clean up and goodbyes

It’s always amazing how quickly everyone has become firm friends and the boat and its routines seem so familiar. Yet it’s time to wrap it all up and head home. We’ll get the boat back to how we found it, sign logbooks, exchange emails and disembark by 1200hrs (we prefer if you don’t, but if you need to catch a ferry or flight, you can leave as early as you need to on the last day).


  • You should join the boat in Marin, Martinique after 1200 hrs on the start date. (Watch leaders see below). 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 Port Antonio, Jamaica at 1200 hrs on the end date.


  • Martinique airport is Fort De France (IATA code: FDF). Norwegian offers very cheap flights from England and Air France and Air Caraibes also offer very cheap flights from Paris as Martinique is a French territory (look for around £450 return!).
  • From the USA you can get flights from Miami or Fort Lauderdale.
  • We can often find cheap long haul airfares, so do fill in our flight finder if you would like us to help.


  • Watch leaders should join the boat 24 hours earlier at 1000hrs  in order to have a day of training and preparation.


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 you 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.


Longer passages offshore and prolonged periods at sea. Usually some coastal cruising at either end.


  • Top quality 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