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Sail from Jamaica and explore the coast of Cuba

Sail from Jamaica and explore the coast of Cuba

Coastal Sailing



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Two weeks of adventure sailing up the coast of Cuba, exploring UNESCO listed cities, deserted paradise islands and extraordinary communes.

Cuba remains one of the most spectacular coasts to sail and explore, with so many hidden treasures that are only really discoverable by sea. We start on the coast of Jamaica for an exhilarating overnight sail across a stretch of the Caribbean Sea before making landfall in southern Cuba. We then work our way north, mixing visits to intoxicating Cuban towns with anchoring off islands fringed with coral reef and flamingoes. Two incredible weeks of adventure sailing and exploring! NO PREVIOUS SAILING EXPERIENCE REQUIRED. JOIN SOLO OR AS A GROUP

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This is a typical itinerary for Jamaica to Cuba. Your trip may be slightly different in length. What makes adventure sailing expeditions so special is that there can be no fixed itinerary and so no part of this is guaranteed. It is indicative of a typical expedition to this region. The wind and the weather ultimately shape what’s possible each day (as do the ever changing Cuban regulations!) but that’s what the adventure is all about!

Day 1

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, sipping a rum punch and enjoying the surroundings. If you have come a few days early why not visit Reich falls, considered to be the most beautiful of Jamaica’s waterfalls or you could arrange a rafting trip on the Rio Grande.

Day 2

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. 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 learning to sail a powerful Clipper 60! By the end of the day you’ll understand the basic manoeuvres like tacking and gybing – even though there’s more to learn and practice every day. We’ll probably anchor in Ochos Rios for the night.

Day 3

Spend the morning exploring ashore and stocking up in the market. After lunch we set sail across the Caribbean on a 120nm passage to Santiago de Cuba. Expect fantastic constellations and a great sailing breeze as we head northwards on the reliable easterly trade winds.

Day 4

Arriving at first light it will take us a few hours to clear customs. We’ll be visited by various authorities: customs may bring a sniffer dog, the ministry of health will check we’re all fit and well, agriculture will inspect our food stores for parasites and the Guarda Frontera stamp our exit papers from Jamaica! It’s quite a process but also an insight into the inner workings of a very unusual country. Once we’re given the all clear it’s time to head ashore and discover Cuba.

Day 5

We’ll aim to spend a whole day in Santiago to give everyone time to wander the streets, visit museums and sip a few mojitos. There is so much to do here but an evening of music and dancing is not to be missed.

Day 6

After stocking up on food in the local markets (which is an experience you won’t forget in a hurry) we sail towards the beautiful coral islands of the Jardines de la Reine. It’s an overnight passage and by now everyone will have learnt the basics of chart work and be confident at putting together a passage plan.

Day 7

After a 24-hour passage we arrive in a beautiful chain of islands. We’ll find somewhere sheltered to drop the anchor such as Cayo Coco, and it won’t take long before everyone has jumped over the side for a swim in the crystal clear water.

Days 8-10

The trip changes pace here as we’ve done most of the miles we need to cover so we spend a few days relaxing, snorkelling and swimming in the pristine waters of the Jardines de la Reine. There are no settlements and few other boats apart from the odd fisherman selling fresh lobster. You’ll soon know how to pilot your way through gaps in the coral reef, reading the colour of the water to know the depth and navigating safely into uncharted territory. Each cay brings with it the opportunity to go and discover the best spot for snorkelling or relax on an unnamed beach. Don’t rely on the guide books here, this is well off the beaten track!

Day 11

Time to return to civilisation, and we do it in style: after anchoring in the Bay of Casilda we’ll take a taxi inland to the town of Trinidad. Don’t be surprised if your taxi is a pink Chevy from the 50s! Trinidad is a UNESCO world heritage site and much loved by Cubans and tourists alike. With it’s brightly coloured houses and charming colonial architecture you can easily spend a day in this time warp where a horse and cart are still a common sight.

Day 12

For our penultimate night on board we anchor off the pretty Cayo Blanco de Casilda. It’s a great snorkelling spot and wonderful place to watch the sun set with a mojito, reflecting on the past two weeks.

Day 13

An early start sees us set sail for Cienfuegos. If the trade winds are in full swing it will be a down wind blast with the mountainous coastline to starboard and we might be able to get the spinnaker up. The approach to Cienfuegos is a fun final pilotage exercise, with a narrow entrance to a big inland sea and complex buoyed channels. It’s the perfect way to put everything you’ve learnt into practise. Once we’re checked in to the marina we’ll celebrate the end of an incredible trip in a roof top bar with a live band (compulsory) and perhaps some singing and dancing (optional).

Day 14

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


You join the boat in Port Antonio, Jamaica, after 1200 hrs on the start 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 Cienfuegos, Cuba at 1200 hrs on the last day.

Fly in to Norman Manley International Airport in Kingston (IATA Code: KIN). You will fly out of Havana (IATA code: HAV) There are buses that go to Port Antonio, leaving as soon as they are full and costing as little as £5. It is a beautiful journey through the mountains and takes about three hours. You can take a taxi but there is no need to and it can cost close to £100.


The buses usually run three times a day and cost about £20. They are operated by Viazul and you can see the schedules here


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.



It is your responsibility to ensure you have any necessary visas or tourist cards to visit Cuba. This should not be an issue for most people, but if your are a US citizen there may be restrictions on whether you can go. Rubicon 3 take no responsibility for securing your visa and cannot refund your trip if you subsequently fail to obtain a visa or tourist card. The following company is very helpful and can usually sort you a visa /tourist card very fast



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.


Mostly day sailing, but off the beaten track with fewer facilities and an adventurous mindset required!


  • 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