header cover
logo

Log in

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.

Why book a holiday with Sailsquare?

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

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

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

88 reviews

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/24/2026

Julie D.

-

NL

I had such an amazing week sailing through the Sporades with Gianfranco. From the moment I arrived, I felt very welcome. The boat is absolutely beautiful, very well looked after and always incredibly clean. What I especially appreciated was how much effort Gianfranco puts into making everyone feel comfortable and at home on board. I really enjoyed learning more about sailing from him and getting some actual sailing experience along the way. And then there is the food! Gianfranco is an amazing cook and prepared some of the best lunches and dinners I’ve had in a long time. One of my favourites was a fish risotto with fresh prawns, squid and other freshly caught seafood for lunch. Eating something that fresh and delicious on the boat, surrounded by the beautiful Sporades, was definitely one of the highlights for me. I also feel very lucky with the people I shared this experience with. I came for a sailing trip and left with new friends, new sailing experience and so many beautiful memories. I had a truly wonderful time and will definitely look back on this trip with a big smile. Thank you Gianfranco for making it so special! ⛵️🇬🇷
avatar image

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/23/2026

Miguel M.

-

ES

[hidden] is a beautiful, safe, comfortable, and extremely well-maintained sailboat. Gianfranco loves sailing and a big smile appears on his face every time the sails are up and the engine is turned off.  No need to say that he is a skillful sailor, but apart from that, he is a fun and kind person, well-organized, and he made easy all the logistics about the trip. The crew was invited to participate in all maneuvers, and I enjoyed that a lot. I highly recommend the experience.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/22/2026

Aida K.

-

BA

I did the Sporades Experience tour and it was fantastic. What I liked the most was the mix of marina nights and sleeping at anchor. Every other night we stayed in a different marina, which gave us time to walk around and discover another island. The other nights we slept at anchor under the stars. Honestly, that was one of my favorite parts of the whole trip. Our captain, Gianfranco, was a great captain and an amazing cook. He enjoyed preparing delicious food for us, and we definitely ate very well. He may not always be the nicest person, but he is the best captain. He has a big heart, although he does get mad when I spill a drink or do not turn off the light. Maybe because he is a perfectionist! The boat was spotless, clean, well organized and very well maintained. You can tell Gianfranco takes a lot of pride in his boat and knows exactly what he is doing. He is well recognized in the sailing community, and after spending a week on his boat, I can understand why. Most importantly, I always felt safe with Gianfranco, and that means a lot to me. I joined this trip by myself, shared a cabin/bed with another female traveler, and ended up making great friends. Seven days later, I left with a lot of great memories, great food, beautiful islands and people I hope to meet again somewhere in the world. Getting on Gianfranco’s boat is a privilege — but don’t expect babysitting! He expects you to be part of the crew, not a passenger waiting to be served. And honestly, that made the experience even better.

From Skiathos to Athens

09/14/2026

Elizabeth B.

-

AR

Beautiful week of sailing. Fantastic places

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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!

    Sporades: the best travel ideas

    Other travel ideas

    Let's talk Sailsquare!

    HuffpostSailing todayYahoo!

    Secure payments

    MastercardVisaGoogle PayApple Pay

    © 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964