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Yacht sailing holidays & skippered tours in the Sporades

Discover the magic of sailing holidays in the Sporades! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

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Reviews - Yacht sailing holidays & skippered tours in the Sporades

77 reviews

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The Sporades Islands: A Hidden Paradise of Greece

07/27/2026

Clara P.

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IT

As a first boat holiday experience and overall it was positive; Andrea is a very good skipper and has a good character. The only flaw is the somewhat reduced space, I think the boat is suitable for a group of up to 6 people so that you can move around more easily, and I would have preferred a slightly more organized management of meals. We have seen wonderful posts and I hope to be able to repeat the experience.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

07/21/2026

Giulio M.

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IT

My wife and I have just spent an unforgettable week in the Sporades islands on a beautiful, extremely comfortable and welcoming sailboat. Skipper Gianfranco proved to be an exemplary professional, very prepared and always attentive to everyone's safety. Thanks to his knowledge of the area, he took us to coves sheltered from the wind, making us discover real corners of paradise In addition to his technical skills, he was able to create, right from the start, a relaxed and fun atmosphere on board; He has always been very helpful in explaining sailing techniques, advising things to see on land, showing us the best places to taste local delicacies or simply having a chat in front of a sunset. A big thank you to Gianfranco.
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The Sporades Islands: A Hidden Paradise of Greece

07/15/2026

Valerio R.

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IT

Fantastic experience
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Sporades Experience: Freedom, Turquoise Sea and Greek Magic

06/28/2026

Raffaele S.

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IT

I have taken several sailing holidays, some of them with Sailsquare. Gianfranco is certainly a man of the sea. Unfortunately, my experience was not positive. The atmosphere on board has always been very tense, linked to the fact that it makes you feel like you are an (unwanted) guest in his home. On several occasions he addressed other members of the group in a rude and rude way, if not to me. In a week he has never used the tender nor allowed anyone to use it. Finally, I did not find the economic requests transparent: on the site a sum of 50 euros is specified as a starter pack (in addition to the common fund) while the day before leaving he sent a sort of personal vademecum in which he requested a total of 500 euros from the 8 participants, as well as requesting, before returning to port, an additional 50 euros. Ultimately, beyond the economic aspect which is not very relevant to me, I did not spend a relaxing week off work but in a very heavy and negative climate. I am very respectful of others and it would be correct to receive the same... especially if they pay you.

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6 reasons to choose the Sporades for your next sailboat or catamaran holiday:

  • Beautiful vegetation - the Sporades are a Garden of Eden dotted with olive groves and fragrant fruits trees.
  • Enjoy the paradise of Greece, minus the crowds.
  • Explore Skopelos, the famous island that was the setting for the film Mamma Mia.
  • Swim in the waters of Alonissos, a popular area with travellers and with dolphins.
  • Taste a skopelitiki tiropita, greek cheese pie, a specialty of the Feta region.
  • To discover the Koukounaries, a special beach destination of Skiathos, one of the most glittering islands of Greece, with 1,200 meters of gold, silky sand.

The best destinations to visit the Sporades during a sailing holiday with a skipper

Located approximately 120km north of Athens, off the eastern coast of Greece, the Sporades archipelago is one of the lesser known of the Mediterranean. Luxuriously green, with a multitude of beautiful beaches, and irresistible blue waters, the Sporades are a great destination for nature lovers. Only four of the 24 islands - Skiathos, Skopelos, Alonissos and Skyros - are inhabited, and the further you go from the mainland, the more private the islands become.

Sailing holidays in Skopelos

People claim that Skopelos is the greenest island in the Aegean, and they may be right. A paradise for nature lovers, Skopelos is home to a wide variety of wildlife thanks to its vast forests and magnificent coastline. The island, once a Cretan colony, has a number of archaeological sites as well as 360 ​​churches, monasteries, and convents. There is a vibrant nightlife and the islanders are very proud of their cuisine. Its ideal setting and unspoiled charm makes Skopelos a popular holiday destination, especially for families and couples. Skopelos became famous thanks to the Hollywood film Mamma Mia. The picturesque church of Agios Ioannis Kastri, where the film's wedding scenes were filmed, is known as the Mamma Mia Church! The two main villages of Skopelos are Skopelos Town and Glossa. Perched on top of hills, these two villages offer a breathtaking view of the Aegean Sea. From your sailboat you will take pleasure in discovering the sublime beaches of Skopelos.

Sailing holidays in Skiathos

Skiathos is the most visited island, part due to the fact that it is the home of the major international airport, part due to its famous sandy beaches. Here, everyday between sailing, you can alternate tavern as you take some time to cool off. Away from the coast, there are isolated hiking trails and Byzantine monasteries. The monastery of Kounistra, built in the 17th century, has survived until today in its original form. One of the impressive symbolic locations of the island.

Sailing holidays in Alonissos

Alonissos, a more rugged island, lies in the middle of a marine park and is surrounded by a group of uninhabited satellite islands. Off the beaten track, by boat is one of the best ways to get to this island. Perfect for those who love remote places, and nature lovers, as it is a great place for hiking. There are many different plants and animals, including rare seals.

Tips to help you to better plan for your next sailing holidays in the Sporades:

All you need to know about your next cruise in the Sporades aboard a sailboat.

When to go to the Sporades for a sailing holiday

  • The region enjoys a warm climate for a large part of the year, however, it is recommended to sail in the Sporades between early April and late October.
  • Holiday prices

  • You can find experiences for a week in the Sporades with a skipper from €500 per person. This figure excludes roundtrip transportation. It is important to remember that prices may vary depending on the month of travel and the style of boat.
  • Transport options to and from your holiday

  • The main airport is located in Skiathos. However, we advise you to contact the skipper organising the trip to understand more precisely the most appropriate transportation options.
  • Sailing in the Sporades solo, as a couple, or with friends and family

    Whether you’re looking for options for couples, a whole boat booking for families and groups of friends, or options for solo travellers there are different experiences to suit you. Be it a trip aboard a sailboat or catamaran, you can book one or multiple spots onboard without having to form your own group of travellers. Find like-minded people and return home with new friends!

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