Classic Sail Charters

With our Tall Ship Maybe

This Autumn and Winter, we are offering a unique opportunity to charter your own tall ship, Maybe, and sail along the beautiful Algarve coast. This is a once in a lifetime experience for your friends and family and will give you the chance to experience something truly memorable with your loved ones. You don’t need any previous sailing experience and there are no minimum age limits as there will be full crew on board. By chartering the entire boat for your sailing holiday, you will have the opportunity to customise the experience for your family or friends.

Our tall ship maybe is only in the algarve area during the
winter / spring. Don’t miss your opportunity to sail with her!

Maybe is a classic sailing ketch with 7 sails. In a normal sailing season, Maybe can be found racing around Europe participating in the Tall Ships Races and travelling around the UK and Europe. But due to Coronavirus COVID-19 restrictions, the boat will be spending the next few months near to Portimão. She is currently located on the beautiful Algarve coastline, in the port of Ferragudo Portimão on the southern edge of Portugal. Over the winter, where most of Europe is cold, the Algarve holds its warm temperatures offering great winter-sun family sailing experiences.

As well as the exhilarating sailing, you will also get the opportunity to explore the coastline using the kayaks and paddleboards that we have available to our guests.

For someone who has never been sailing before, I was very apprehensive but still excited about the whole experience. It really surpassed my expectations. The team, the food, the spontaneity of sailing and learning the ropes was an amazing and one of a kind experience.

The crew were lively and really entertaining, great with children and because of having to work in a team, a close bond formed very quickly with everyone onboard. When asked by the captain at the end, what I thought of the experience, only one word came to mind, ‘phenomenal’ – it really was!

Marley, aged 10.


Marley J - TS Maybe August 2020

My family and I recently had an amazing opportunity to spend time onboard the Tall Ship Maybe. I was a little apprehensive about it at first as we have two young children aged three and one. However, a quick visit to Maybe soon reassured us that we were making the right decision as she is a very spacious, sturdy boat, with great Family sized cabins and all the necessary safety equipment for children.

Maybe is incredible in every way. She is a beautiful boat and coupled with her outstanding crew is a dream to sail for both the experienced and inexperienced. As well as having exceptional knowledge and control of the boat, the good-humoured and approachable crew also provided magnificent food, and were fantastic with the children. They involved them whilst sailing, giving each of them little jobs and tasks, and once anchored played games with them and even had them baking bread and pizza. They all worked tirelessly to ensure everyone was happy every minute of the day.

Our trip was extremely well planned with the perfect balance of sailing and stop off points for adventure activities like kayaking, paddle boarding, and snorkelling. There was nothing better than having drinks on deck in the evening beneath the stars whilst the children were close by, fast asleep in their bunks. Then, after an action-packed day of sailing it was so nice to retreat to your bunk and be rocked gently to sleep by the Ocean.

The trip left us with amazing memories and a burning desire to get back on board as soon as possible.

Christina S – TS Maybe – August 2020

Find Our More

If you are interested in finding out more about our exciting Winter Sail Charters, please fill out the following form:

  • If you are from another country, please give the country code too.
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