Cheap sailing holidays: Mediterranean and Greece

April 1, 2019

Cheap sailing holidays: the Mediterranean, and Greece


Are you looking for cheap sailing holidays? With Sailsquare, your sailing holiday opportunities are almost limitless! Many see sailing holidays as a luxury reserved only for the rich or well-connected, our aim is to make sailing holidays accessible to all.

Our platform, based on sharing economy principles, is able to put the needs of travellers first – by offering sailing experiences, at a fair price. Sailsquare’s unique, one berth booking, enables a number of individuals, couples, or small groups to come together, and contribute collectively for the cost of a whole sailboat or catamaran.

Currently, there are skippers in 95 destinations around the world using Sailsquare. All of this means you can find the trip that is right for you, in your dream destination, and at the right price.



Cheap sailing holidays: the Amalfi Coast, or the Greek Isles?

Through our wide offer of experiences, you can find cheap holidays in Italy and Greece, throughout the Mediterranean, Ionian, Aeolian, Cyclades, and Dodecanese isles – and much more. For anyone still having doubts about sailing holiday prices being too high – in fact, in Greece and Italy, you can find holidays from €400 per week! 

Cheap sailing holidays: an amazing adventure

The concept of cheap sailing holidays are no longer just a dream! Now, you can start planning for that truly unique, bucket list travel experience – whether that’s exploring wilderness in a remote destination, or cruising along the coast of a picturesque coastline – you can find it all here. Both of Italy and Greece are luxury travel destinations, and home to some of the world’s most famous waters. Greece, for example, has almost 3,000 different islands, each with their own story, and charm to be explored.

  • Find out more about the treasures of Italy, including the Amalfi Coast, Sardinia, Lake Garda, and the Aeolian Islands: here.


  • Learn more about the most beautiful destinations in Greece, including Corfu, Mykonos, and Santorini: here.

Flotilla sailing holidays: the more, the merrier

A flotilla holiday is a group of travellers, coming together to share their sailing experience with each other. This means between 2 and 10 sailboats sailing together, and exploring the destinations waters and hidden treasures all together! The Mediterranean is one of the best areas in the world for flotilla experiences, and this is because there are so many different destinations within and in the surrounding waters. The same can be said throughout Greece, where island hopping from coast to coast has become a popular, and unique way of seeing more of the Greek Isles than would be possible by land.

  • Learn more about what a flotilla holiday actually is, and browse our current listings: here.