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The Atlantic Islands – Madeira – Azores

The Atlantic Islands – Madeira – Azores

Offshore & ocean sailing




Ocean sailing at its best, from Madeira to the Azores

If you've ever dreamt of what it would be like to be sailing out on the open ocean, hundreds of miles from land, then this is the perfect adventure for you. Starting from the Portuguese island of Madeira, over 700nm of Atlantic Ocean lies between you and your destination, the volcanic archipelago of the Azores. Sailing on one of our incredible 60' ocean going yachts and with two top class instructors to guide you, you will experience life on the high seas in all its majesty. Get ready for two weeks of sailing, training and exploring. Two weeks full of challenges, exhilaration, excitement and wonder. Get ready for open ocean sailing from Madeira to the Azores! (A Yachtmaster Ocean qualifying passage for watch leaders).

Sailing location image
Route Map Image

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.

Day 1: Joining day

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. Madeira is a wonderful place to be in the winter, with a warm climate, lovely coast and some great views and sunsets.

Day 2: Briefings and training on the Madeiran coast

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 may well stop for the night in Funchal, the capital of Madeira.

Day 3: Preparation and planning for the ocean passage.

With over 600nm 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. It’s fantastic training for everyone and we’ll be checking sails, storm sail, drogues and all the other equipment needed for this type of voyage. All the time we’ll also be checking the weather, looking for the ideal window for the passage.

Days 4-8: Passage to the Azores

As soon as the weather is right, we will cast off the lines and turn north west to the Azores. We have around 700nm 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 are whales and dolphins to be spotted, celestial navigation to be tried and there will still plenty of time just to gaze out over the ocean and muse!

Days 9-10: Arrival in the Azores archipelago

Around the end of day 5, we should be pulling into the cluster of volcanic islands that make up the western sector of the Azores archipelago for some very well earned rest and recuperation. We’ll stop for a good 24 hours here to eat ashore, have some beers, and catch up on any sleep.

Days 12-14: Cruising in the Azores

There is some wonderful cruising to take up any remaining time we may have. Pico with its eponymous volcano is not just the highest mountain in Portugal but also the highest elevation of the Mid-Atlantic ridge. It’s a lovely place to hike, take in some spectacular views and just to appreciate just how special the Azores are. São Jorge is one of the most scenically dramatic and friendly islands in the Azores. Its picturesque capital, Velas, is a sleepy harbour town dating from the mid 1400s and has a delightful traditional Azorean bandstand in the main square. Terceira is home to the Azores’ oldest city: UNESCO protected Angra do Heroismo whose cobbled streets, historic architecture and friendly population help give the city a wonderfully relaxing, quiet charm. It’s also a very volcanic landscape, formed by criss-crossing lava flows which have created spectacular cave systems and natural seawater swimming pools to enjoy. Wherever we get to go and explore, on the penultimate day we’ll make the passage south east to the volcanic island of Faial and Horta for our final sail of the trip. Horta is often called the most colourful marina in the world! This is the island’s capital and a fun and lively place. A well-established haven for yachtsmen and whale watchers, you will likely meet other sailors en route across the Atlantic Ocean and you can swap dreams and adventures over a beer or coffee. That night we’ll have a big meal and celebration, no doubt trading memories, laughter and sharing future plans.

Day 15: 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 Quinta Do Lorde, Madeira 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 on the start day, that is fine. We will ask you closer to the time to let us know your travel details.
  • The marina is a 20 minute taxi ride from the airport.
  • You will disembark the boat in Horta, Azores at 1200 hrs on the end date.


  • Madeira airport, known as Funchal  (IATA code: FNC) is well served by British Airways, Easyjet, TAP, TUI and others.
  • Horta (IATA code: HOR) is served by Ryanair, TAP and others.

Airline websites

British Airways






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.


Extended periods of offshore sailing with night watches.


  • To be a watch leader on a Rubicon 3 ocean passage, we require you to have sufficient skills and experience to be able to approach the role meaningfully. This means you should have a minimum of RYA Coastal Skipper practical and theory. We accept international equivalents. After booking, you will be asked to provide evidence of your qualifications.
  • On arrival, we will ask you to complete a short theory test to ensure that you are at the required level. If you are able to complete RYA Yachtmaster Coastal theory questions, you will be fine. If you are not at the required standard, we will downgrade you to a standard crew member.


  • On booking, you will receive a copy of the Rubicon 3 Watch Leader’s training manual. This is an invaluable resource and you should try to read as much of it as you can before joining.
  • You should arrive at the boat the day before the advertised start time, being ready to start studying at 1000 hrs. You will spend a full day learning about passage planning, the yacht and helping prepare the yacht. You will be able to stay on the boat that night
  • There is an additional fee of £150 to cover these extra training costs.


  • 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