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Adventure sailing along the coast of Cuba

Adventure sailing along the coast of Cuba

Coastal Sailing



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Nowhere in the world is quite like Cuba and here's an amazing opportunity to get to know this fascinating country in an adventure sailing holiday unlike any other.

Cuba's unique culture, iconic music, paradise islands and beautiful towns make it one of the most spectacular and exciting sailing grounds in the world. Jump from Hemmingway's haunts to a picture postcard island fringed by coral reefs and home to flocks of flamingoes, with the intoxicating lure of Havana to round off your adventure. Throughout, you’ll be fully involved in the sailing and planning where to go each day, receiving top class training and tuition and constantly building your skills and experience. No previous sailing experience is required to join this once in a lifetime voyage. You can join solo, as many do, or come along with a group of family or friends.
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This is a typical itinerary for the Cuba Explorer. You 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 – Welcome to the team

Jump on board between midday and 1800h and make yourself at home. We’ll be berthed in the harbour of Cienfuegos, a lovely city with colonial era buildings and long waterfront looking out onto the harbour. Today is all about relaxing, starting your sailing holiday and getting to know the boat and your new crew – it never takes long for the laughter to start.

Day 2 – Learning the ropes

Quite literally! Your skipper and mate will guide you through all the basic skills you need to sail a powerful 60’ yacht. We assume no knowledge so that everyone can be fully involved, whatever their experience and, as usual, there’s no such thing as a silly question. You’ll continue building these skills throughout the trip, so don’t worry about getting everything first time. We’ll probably anchor off the pretty Cayo Blanco de Casilda for the night and have a cold beer under the incredible Caribbean starscape.

Days 3 & 4 – Sail to and explore Trinidad, UNESCO world heritage city

After a morning swim or snorkel we sail in to the bay of Casilda, from where we can jump in a taxi (probably a 1950’s Chevy) for the short journey to Trinidad. It’s a time warp with a beautifully preserved old town full of colourful buildings, cobbled streets and markets – a must on any Cuba itinerary and we’ll likely spend a full day here.

Days 5 & 6 – Sail under a carpet of stars to Cayo Largo

An island 90nm west of Trinidad, Cayo Largo is famous for its powder soft beaches and turquoise water. It’s an exhilarating sail and, as the sun sets, we’ll likely have a sky full of constellations as there’s no other light at all. You will never see night skies like this! We’ll navigate our way through the reefs to the marina which comes complete with its own resident crocodile. Cayo Largo is stunningly beautiful and has some of the most beautiful beaches in the world. A perfect place to explore ashore and swim in the warm Carribean sea.

Days 7 & 8 – Exploring the majestic wilderness of the Cuban islands

For the next two days, we will wind our way through these beautiful, remote Cuban islands. Most are far from the beaten track and can seem like deserted islands from old adventure stories. Occasionally fishermen will barter for their catch and we can have a gorgeous fresh seafood dinner. There is wonderful snorkelling here, with coral and reef sharks and huge turtles drifting by. Elsewhere you might see a pink flamingo wandering by. A true sailing and exploring paradise.

Days 9 & 10 – Sailing to the Isla de la Juventud (Island of the Youth)

Continuing west we head on to Siguanea, renowned dive site and rural idyll. It’s a fantastic sail around the southwest tip of the island and up into the bay. We’ll spend a whole day here to give everyone time to explore either above or below the surface. Those staying on dry land should visit the main town of Nuevo Gerona (where you’ll probably be the only tourists) for an encounter with real Cuba whilst those venturing into the deep will discover a mysterious wall of black coral.

Days 11 to 12 – Coral reefs in the western Cayos

There are innumerable islands (Cayos) with sandy beaches and coral reefs between Juventud and Maria La Gorda, our next port of call. Eyeball navigation comes into its own here as we find our own anchorages in between the coral heads and discover this untrammelled cruising ground before relaxing in the tiny dive resort at Maria La Gorda for a night before our big passage to Havana.

Days 13 to 14 – Sailing to Havana

Now we head out into the Gulf Stream for our final 250 mile passage to Havana. We can expect a really exciting 36 hour passage here (possibly with a stop en-route) Rounding the northwest cape is exciting and exhilarating and, as we work our way along the coast, we’re getting ever closer to the reward of Havana, the beating heart of Cuba and a truly special place.

Day 15 – Cleaning, debriefs and goodbyes

The end comes all too soon, but there’s no doubt that you’ll go home with some unforgettable memories and having had a huge amount of fun. After cleaning up, swapping photos and saying goodbye to the boat and the crew, you’ll be free to disembark from 1200h.



You should join the boat in Cienfuegos, Cuba 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 probably fly into Havana and will need to connect from there. The best way is to share a taxi with other crew (about £100 and 2.5 hours) or there’s a fascinating bus ride (£20 and 5.5 hrs). You will disembark the boat in Havana on the last day at 1200hrs. Many crew fly into Havana the day before, stay the night and then get the bus. Air France can be a good option. Please get in touch and we will happily help you with your travel plans.


Havana (IATA code: HAV) is well served by many airlines.
Remember we can often find really cheap long haul flights, so do use our flight finder if you don’t find the flight you want.


The buses usually run three times a day in each direction between Havana and Cienfuegos 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 may have an occasional overnight sail.


  • 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