Age range


Start port

Cascais, Portugal

End port

Santa Cruz, Tenerife






Competent Crew

Voyage code



Up to £300 (under 25s)

Voyage highlights

Sail from Cascais to Santa Cruz for some winter sun, sea and thrills!
Combine adventurous offshore passage sailing with relaxed island exploration
Learn elements of passage planning and practise your celestial navigation
Previous sailing experience will help to get the most out of the adventure
Your participation will directly benefit our vital youth work

This voyage from Cascais, Portugal to Santa Cruz de Tenerife is a great introduction to offshore passage sailing for the novice or leisure sailor who wants to widen their sailing experience while enjoying some winter sun.

On this voyage starting in Portugal’s Cascais, you’ll cover around 1,000 nautical miles and spend multiple days at sea, working in a watch system from the outset, before cruising the Canary Islands to Santa Cruz de Tenerife. The weather is likely to turn increasingly favourable the further south we go, and you should be in shorts and t-shirts by the time we reach Tenerife!

Onboard, you’ll meet like-minded individuals, aged from 18–65, who you’ll work together with to form one crew.

Our crews come from a wide range of backgrounds and have varying levels of experience, but they all have one thing in common – the motivation to step outside of their comfort zones and sail our iconic yachts to exciting destinations.

Our Challengers are 72ft ocean-going steel yachts, constructed to withstand the Southern Ocean. Launched in 2000, they raced round the world in two editions of the BT Global Challenge, the route taking them against prevailing winds and currents, through some of the most challenging sailing conditions on the planet.

This means that our Challengers are the perfect vessel for this type of voyage and will make it an exhilarating and memorable experience!

Since 2008 our four Challenger yachts have provided TSYT with a unique and positively challenging platform for our Youth Development and Outdoor Learning programme, which is supported by our adventure voyages for adults.

Previous sailing experience is preferred for this voyage. Please do not hesitate to call us on 02392 832055 if you would like to discuss whether this is the right voyage for you.

Post your departure in Santa Cruz de Tenerife, the boat will undergo safety checks and preparation in readiness for our next Canary Islands adventure, starting on Monday 4 December. For more details on this, click here.

If you’re interested in more than one Canary Islands voyage, you can take advantage of our exclusive bundle offering. Contact our Reservations Team for more information:

Places you'll visit

After your departure from Cascais and initial yacht familiarisation and safety training, your sailing route will be governed by the wind direction.

The first potential stopover is Madeira (after approximately three days of sailing), where, if you’ve made good time, you may have a day off to soak up the sunshine on one its beautiful golden beaches or explore the island via its unique rocky formation trail walks.

Alternatively, if the breeze is unfavourable for Madeira, you might push on to Lanzarote and cruise the dramatic volcanic coastline of the north-eastern Canary Islands, before arriving in the vibrant port of Santa Cruz de Tenerife, with its great tapas bars, restaurants and lively indoor market.

Takeaways from your sailing adventure

New skills. Increased confidence. New friendships. Winter sun!

There will be plenty of photograph opportunities to ensure your memories are lifelong, so be sure to pack your camera! In addition to the stunning landscapes, you may also spot marine wildlife such as, dolphins, seals and fin whales.

Over the course of the trip, you’ll learn how to helm a large, powerful yacht offshore, experience the challenge of sail changing at sea, and brush up on your navigation, chartwork and knot tying.

There is a sextant onboard, along with the sight-reduction tables in case you fancy taking some sun or star sights on passage. This voyage provides the ideal opportunity to learn the basics of passage planning and celestial navigation.

Our adventure sailing voyages are fully participative. Over the course of the trip, you’ll experience steering the yacht, sail handling and ropework, as well as learning how to keep safe onboard.

Our crews get involved in every aspect of running the vessel, so expect to be working in a watch system for much of the voyage, and taking your turn at helming, sail handling, cooking and cleaning.

Further information

Once we receive your booking, we’ll need to review all of the information you’ve provided including your medical history, and so your voyage will not be confirmed until you’ve received an email accepting your booking. Please do not book any travel for the trip prior to receiving this email.

The Skipper will determine the final route depending on the weather and other variables.

For this voyage, we recommend you pack shorts and t-shirts as well as warmer clothes.

If you share our values and are keen to do more, you may be able to support our mission further by joining the TSYT Volunteer Crew.

Your Skipper can recommend you for our Watch Leader Training programme if they feel you have the skills and attributes that we’re looking for.

All meals onboard are included.


You’ll hopefully get the chance to complete the RYA Competent Crew course while you’re onboard.

The cost of your RYA certificate is included in the price.

RYA logbooks are available for purchase onboard at a cost of £6 (Skippers are only able to take cash for this).

Duke of Edinburgh's Award

All our voyages of four nights or more qualify for the residential section of the DofE Gold Award.

Please let our Reservations Team know before sailing if you want to use the voyage for this.​​​


You’ll be asked to enter your passport details as part of the booking process. If you don’t have these to hand, please contact us as soon as possible after submitting your booking form to let us know your details, as we cannot accept your booking without this information.

You will also need to present your valid passport to the Skipper at the start of the voyage.

TS Challenger Current Navy 1



Vessel Details

handbook challenger


Challenger Handbook


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