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Madeira sailing holiday

Madeira sailing holiday


21 – 28 February 2021 (£999)

20 – 27 November 2021 (£999)




Explore the Portuguese island of Madeira

A wonderful coastal sailing holiday in the winter sun that gives you the chance to sail around this fascinating island, stopping in somewhere new every day. From the capital Funchal to the extraordinary Islas de Desrthas, Madeira is blessed with great wind, a warm climate and some truly gorgeous anchorages, harbours, towns and nature. For a gentle winter sun sailing holiday, this will always be hard to beat.
Sailing location image
Route Map Image

Far out in the North Atlantic is the stunning Madeira archipelago. Comprised of the main island of Madeira, the neighbouring Porto Santo and the Islas Desertas national park there is so much to explore. Once part of the trade routes Madeira is a half way house between Europe and the Caribbean: it’s sub-tropical climate, banana plantations and infamous Rum Poncha make it a great place for a winter sailing get-away. There’s no overnight sailing on this trip, so it’s perfect for those wanting to build sailing skills and have plenty of time to explore ashore on a fun, relaxed voyage.

Day 1 – Joining day

Meet your fellow crew members and Hummingbird, your home for the next week in the lovely marina of Quinta do Lorde. It is a spectacular setting beneath high red cliffs. With a salt water swimming pool hewn from the bedrock and filled up each high tide by the mighty Atlantic it’s a great place to start the voyage. Today is all about getting settled in, meeting the skipper and mate and easing into life on board a 60’ expedition yacht.

Day 2 – Learning the ropes – literally!

After a morning of briefing alongside the dock we’ll head out to sea, hoist the sails and coach you through the different techniques required to handle a powerful 60’ sailing yacht. It’s a fun and exhilarating day where we introduce all the key concepts that you’ll be using throughout the week ahead. Anchor in a secluded bay next to the beautiful point of Sao Lourenco for the evening to watch the sun go down, and maybe even take an evening dip.

Day 3 – Sail Madeira’s south coast

Funchal lies 30 nautical miles west of Sao Lourenco. It’s a fantastic six hour sail down the coast and chance to build on the lessons of the day before. If we’re lucky we might be joined by a pod of inquisitive pilot whales as we sail past high peaks and forested gullies of the volcanic coastline.

Day 4 – Explore Funchal

With a full day to explore Funchal it’s time to head ashore and explore the cobbled streets, vibrant markets and historic centre of this lovely old city. Take a bone-rattling and nerve-jangling toboggan ride down the narrow lanes of the Monte and sample some of the local run Poncha. There’s also time for navigation lessons from our top instructors who will train you how to make a passage plan, enter unfamiliar harbours and research a route.

Day 5 – Wild islands of Ihlas Desertas

25 miles south east of Funchal are the aptly named Ihlas Desertas. This group of three rugged islands are a National Park on account of the rare sea lion colony. They are guarded by rangers so we will need to gain an access permit before departing Funchal. Under way you’ll be putting the navigation training into practise and building on the sailing skills of the previous days under the careful guidance of the skipper and mate.

Day 6 – Fantastic upwind sailing

After a hike ashore in the Ilhas Desertas we’ll head off to the Porto Santo, Madeira’s diminutive younger sibling forty miles to the north east. If the trade winds are playing ball this should be a fantastic upwind sail. We’ll put the Clipper 60 through her paces and enjoy the experience of offshore sailing on such a powerful and capable yacht.

Day 7 – Porto Santo

Porto Santo is famous for its mile long golden beach which is right next to the harbour so it’s a great place for a bit of RnR. We’ll also run some navigation workshops for those wanting to pick up the key navigation techniques our expedition skippers use, anchoring techniques and weather forecasts.

Day 8 – Home run

The final sail is a downwind dash back to Quinta do Lorde. With the North Atlantic trades behind us we’ll fly along, surfing the Atlantic swell and grinning as the boat charges through the waves. Warning: this type of sailing can become addictive! We’ll be back in the marina by 1600, just in time for a quick scrub up before a fun crew meal ashore. There’s wonderful seafood available with freshly caught octopus and tuna often on the menu.

Day 9 – Goodbyes

The end comes all too soon and, after putting the boat back to how we found her, swapping emails and photos it’s time to say farewell until the next adventure! You’ll be able to disembark by mid morning in order to catch flights home at midday.

You should join the boat in Quinta Da Lorde any time after 1200 hrs on the start day. You will disembark the boat in  Quinta Da Lorde from 0800 hrs on the last day.


Fly into and out of Funchal (IATA code: FNC), and from there it is a short taxi ride to the south east corner of Madeira and Quinta Da Lorde.


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 medial issues.
  • For our latest guidance on travel insurance, please read here.


Mostly day sailing, shorter mileage and more time to head ashore and explore. However you must be aware that in this region the weather can turn quickly and we may encounter rougher seas


  • 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