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Madeira sailing holiday

Madeira sailing holiday





Sailing holiday: 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.
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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: November 28 2022. Quinta da Lorde, Madeira
  • End date / place: December 02 2022. Quinta da Lorde, Madeira
  • Full price: £699
  • Deposit: £175


Please see ‘TRAVEL – GETTING TO & FROM YOUR TRIP’ tab for advice on start and end points.



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.

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.

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.

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.

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.

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.

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.

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.

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.


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 need to join the boat promptly at 0900hrs on the start day. We will have a cup of tea and get to know each other and the skipper and mate will talk you through what to expect, find you your berth, help you get your kit packed away and issue you with oilskins, lifejacket and immersion/abandon ship survival suit.


The trip ends at 1200 on the last day at which time you will need to disembark.



    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 anyone aged 18 – 70 years. No previous sailing experience is required for this route


    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 you 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.


    • Oilskins
    • 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 can be earned 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 Trip Notes before booking.