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Ocean sailing between the Atlantic Islands: Madeira – Azores

Ocean sailing between the Atlantic Islands: Madeira – Azores

Offshore & ocean sailing




Ocean sailing holiday: Madeira - 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. Sailing between the Portuguese island of Madeira and the the volcanic archipelago of the Azores, there is over 700nm of Atlantic Ocean between you and your destination. 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 glorious open ocean sailing (A Yachtmaster Ocean qualifying passage for watch leaders).

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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: May 30 2022. Quinta Da Lorde, Madeira
  • End date / place: June 10 2022. Horta, Azores
  • Full price: £1,899
  • Deposit: £475


  • Start date / place: August 28, 2023. Quinta Da Lorde, Madeira
  • End date / place: September 08, 2023. Horta, Azores
  • Full price: £1,899
  • Deposit: £475


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.

Day 1: Joining day

Join the boat at 0900hrs on th first day. 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 at 0900 hrs on the start date. (Watch leaders see below). 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 anyone aged 18 – 70 years. Although this trip is open to beginners, we recommend that you have some sailing experience before, even if it is just an introductory weekend. This will enable you to be confident that a prolonged passage at sea is something that you will enjoy.


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.


  • 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