Age range


Start port


End port






Voyage code



Up to £300 (under 25s)

Voyage highlights

Set sail to Cascais - the Portuguese Riviera – for some winter sun!
Cross the Bay of Biscay in expert style onboard a world-famous Challenger
Experience some serious offshore sailing
Your participation in this voyage will directly benefit our vital work with young people aged 12-25
Previous sailing experience is preferred but not essential

This voyage from Portsmouth to Cascais is made for the adventure sailor who enjoys a physical challenge, is resilient and used to living in close quarters with their fellow crew!

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

The Bay of Biscay can be tempestuous in November but rest assured you’ll be in safe hands onboard one of our Challengers, and skippered by our very experienced and highly-qualified sailors.

Our Challengers are 72ft long and made of steel. Built in 2000 they have raced twice round the world in the Global Challenge races against prevailing winds and tides and were designed for heavy weather.

The Challenger is the perfect vessel for this type of voyage and will make it a unique and memorable experience!

Plus, you’ll be supporting our life-changing youth development work. Proceeds from our adult voyages support our charity’s vital work with young people aged 12-25.

Places you'll visit

At the start of the outward leg, you may stopover at Cowes or Yarmouth, if the weather is good, or head further west with possible stops in Plymouth, Brixham and Falmouth.

We’ll then turn south to get the most favourable wind angle and to avoid the area of the Bay of Biscay where the depth drops from 100 metres to 4000 metres over just a 10-mile distance!

On the way to Cascais, one of the richest towns in the Iberian Peninsula, it’s possible we may visit A Coruña in northern Spain or Porto in Portugal.

Once the Bay of Biscay is behind us there’ll be plenty of time for relaxing, exploring and recovery.

The Skipper will plan to arrive in Cascais the day before your departure on Friday 25 November.

Post your departure in Cascais the boat will undergo checks and preparation for our next voyage starting on Monday 28 November to Santa Cruz in Tenerife. So, if you fancy an extended stay in the Canaries, click here for more details.

If you’re interested in more than one Canary voyage, you can take advantage of an exclusive price package. Contact our Reservations team for more information:

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 land and seascapes, you may spot dolphins, seals and fin whales.

Over the course of the trip, you’ll experience steering a yacht, sail handling, ropework, as well as learning how to keep safe onboard.

We divide the crew into two teams (watches) – traditionally, known as Port and Starboard. In your watches, you’ll take it in turns to be involved in all aspects of sailing the Challenger from looking after her to cooking and cleaning.

Further information

Once we receive your booking, we’ll arrange a call back from our Reservations team to discuss and check your eligibility for this voyage. Please do not book any travel for this trip prior to this.

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

Once we get south of the Bay of Biscay, the weather generally improves and feels warmer. So, we recommend you pack shorts and t-shirts as well as warmer clothes.

There’s a possibility you could be recommended by the Skipper to come back and volunteer as a Watch Assistant or Watch Leader for future Tall Ships Youth Trust voyages.

Meals onboard are included.

Duke of Edinburgh

All our voyages of four nights or more qualify for the DofE Gold Residential award. Please let our Reservations Team know before sailing if you want to use the voyage for this.

Passport and Covid restrictions


You’ll need to present a valid passport at the start of the voyage.

Covid restrictions

You must adhere to any travel restrictions and meet the stopover and destination countries’ entry requirements in relation to Covid-19 (see links below for full details. These are regularly updated and we strongly advise you check at the time of booking and again before travelling).

Our own Covid-19 sailing processes can be read here. Further information is also included with your joining instructions (sent via email) closer to your voyage date.

Government travel guidance for:



Spain and the Canary Islands

Book with confidence

If you or the person you’re booking for, is unable to take part in this voyage due to any of the following:

  • The area you’re travelling from, or to, has issued a COVID travel ban
  • You test positive for coronavirus (and can supply proof)
  • You’re asked to self-isolate (and can supply proof)

We’ll offer you a credit that can be used as payment, or part payment, for a future reservation booked within six months from the date of cancellation. For more information, please contact:

See our full conditions of booking for our T&Cs.

TS Challenger Current Navy 1



Vessel Details

handbook challenger


Challenger Handbook


Book this voyage