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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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The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in the Sporades

64 reviews

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Skiathos Skopelos Alonissos and Surroundings The Fantastic Sporades





Vacanza complessivamente eccezionale Isole bellissime baie frequentate grazie all’ ottimo skipper molto belle complimenti ancora ad alessandro
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Skiathos Skopelos Alonissos and Surroundings The Fantastic Sporades


Rosanna M.



vacanza molto bella e consigliatissima Lo skipper è veramente top !
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Skiathos Skopelos Alonissos and Surroundings The Fantastic Sporades


Rocío M.



La experiencia en el Orpheas ha sido inolvidable, Alessandro encantador, simpático, pendiente de todo y de todos, gran navegante y conocedor de las islas griegas. Las aventuras en motorino incomparables, el grupo excelente, la convivencia buenísima, muchas risas, relax y disfrute total. Deseando repetir
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Alla scoperta delle Sporadi: Skiathos, Skopelos, Alonnisos


Daniele A.



Gentile e morbido Sorridente e allegro Disponibile ed equilibrato Piacevolmente accudente senza esagerare Ottime capacità di semplificazione Fantastiche play list Consigliassimo

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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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