Yacht sailing holidays & skippered tours in the Cyclades
Discover the treasures of the Aegean Sea - a collection of islands
with their own unique charm, landscapes, and coastlines. The
Cycladic Islands act as a brilliant destination to unwind, relax,
and connect with some of the most stunning natural beauty. Explore
the stunning Santorini, Mykonos, and Ios with a passionate, local
skipper.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Yacht sailing holidays & skippered tours in the Cyclades
Manuele is the talented skipper of Mogwli a beautiful and very well kept Kufner 54. After sailing for more than 200 miles together, he is undoubtedly a 5 out of 5. Not only He is a very experienced skipper but surprisingly also an amazing chef, just give him 10 and a sharp knife. His life approach and positive energy will blow you away. He is very communicative, funny and rather clear when delivering instructions to the crew both in Italian and English. We didn't test his Spanish ;) His attitude towards sailing and the crew has been all the way outstanding. He is able to share his knowledge without falling into a classical teaching approach. He is able to stimulate and encourage a very important side of learning: intrinsic motivation. He challenges constantly your awareness about the boat, weather conditions and surroundings stimulating inner reflection. Extremely respectful about the crew members, environment and the sea. As he usually says at the end of a long sailing day: "Super!"
Elias is a quiet, unobtrusive skipper, who leaves great freedom to the passengers and supports them. It does not impose its own presence, as many often do.
A beautiful experience that I recommend to everyone.
Mike immediately proved to be a quiet captain and available to our needs or requests. Making us spend five days of relaxation and fun in the middle of the sea.
I was also lucky enough to find some wonderful travel companions who allowed this experience to prove to be even more enjoyable.
The boat, in addition, offers all the comforts you need to enjoy your holiday.
I invite anyone who is looking for a different way to travel to jump in and try. Because you will have the opportunity to see different places, unforgettable sunsets, endless stars and a crystal clear sea. With the possibility of meeting new people.
To be redone absolutely!!!
Tommaso and Laura are two very pleasant and welcoming people. and caring. They have a great passion for the sea. Skipper very attentive and prepared. Excellent their vegan cuisine, which they made us discover with simple but tasty and very varied recipes. On days of bad weather, when unfortunately we were forced to stand still in port, they organized tours by rental car. All great and highly recommended.
Giovanni and Stefania were amazing. Nice and super professional they made us safely discover the wonders of the Cyclades with a meltemi that did not give up on us for the whole week. Sailing, the real one!
claudio and his partner have created a very special format based on attention to detail and services (kitchen). For some it could be very interesting since there is no galley to do or dinners to prepare, his partner is an excellent chef. If you are looking for a sharing experience, some typical features of the sailboat are a little less. It's a bit like cruising on a sailboat.
George is the owner of the sail boats and he has at least 2 skippers that he works with (Eric & Georgios), so your experience can differ really depending on which skipper you get. George is a really cool guy with lots of great tips and local insider tips for taverns, caves and beaches, however, he is not the skipper. Our skipper was Eric.
Eric is a polite person, we felt safe with him as he is a experienced sailor. Unfortunately, he preferred speaking French on the boat, which wasn’t so nice for the international crowd. My boyfriend was really curious to learn about sailing, but the English communication was an issue for that. I’d recommend the trip for French speaking tourists.
He is also a bit introverted, so if you want to have someone entertaining the crowd, giving proactive advise, then this is not the skipper for you.
However, overall Eric is a great person with a good heart. He brought us to some hidden gems for swimming and knows a few nice taverns in the area.
I didn’t know Andrea and I trusted about his previous references. To be frank he is a great sailor and (maybe much more important) a very honest and nice person. I really enjoyed my time on board and w the crew. I really hope to be in touch w him and I m looking forward to have an other sail trip on his boat!
We had a blast - most relaxing vacations I had in a lobg time. Adriana and Radu are super cool, friendly and went out of their way to nake us feel comfortable on board and to gove us the best greek experience as possible. On each island we were equipped with local insider tipps what to go and see. The boat was super clean, sheets were even changed in the midtime of our trip. We had an amazing trip and would go sailing with them again tomorrow.
Where to begin...
Spiros is without a doubt one of the most attentive, relaxed, talented people we have met- sailing aside. In regards to sailing, Spiros was an absolute wonder to have as a skipper. We had some days with a lot of wind (meltemi) and waves but he was both re-assuring, fun and made the experience exhilarating.
We not only had a wonderful holiday visiting wonderful places but we also made a friend in him. We will be back.
Devon et Hugues
We have been 1 week in the cruise around cyclades islands, and It has been a beautiful experience. Everything was perfect, the places, where we have been, were so nice, thanks to Istvan who has done this possible, He is so Kind, always telling us some anecdotes. Thanks for this experience!
This cruise with Nikos and Mathilde was our first sailing cruise, and we loved it! The itinerary had to be revised due to the weather conditions and we finally sailed to the Saronic Islands, but the experience remained exceptional. What a feeling that of letting yourself be carried away by the wind. Nikos introduced us to sailing and maneuvering, and thanks to the paddle board and snorkeling equipment, we enjoyed the marine pleasures to the fullest. Nikos and Mathilde immediately put us at ease, knowing how to be very flexible and responsive, eager to satisfy the slightest of our desires, without ever imposing themselves. Mathilde's good dishes are a real plus!!! Greece is a beautiful country, and the Greeks a charming people. We visited different traditional villages and we will never forget the effervescence of this small port of Hydra, where everyone was busy making a small place for our sailboat... THANK YOU.
This was ou first time joining this type of holiday and I have to say that it went beyond expectations.
First of all the communication with Sandrine and Jean-Marc have been very prompt and clear from the beginning.
The boat is exactly (or better) as in the pictures and description provided, very comfortable.
Sandrine and Jean-Marc have been more than just skippers, they have treated us like friends and did their best to accommodate our wishes. I have had few episodes of sea sickness and they adjusted the trip to make sure I wouldn't suffer the sailing time for too long.
The islands they have chosen for the itinerary were not the usual touristic spots, they really took us to beautiful places like Pirates Bay in Milos, unforgettable.
They were very kind by preparing us breakfast and lunch or dinner in case we wanted to stay on the boat.
Also, we didn't lack of privacy at all and we have strongy appreciated that. I will definitely consider to joining them again for another holiday!
vacanza PERFETTA! La barca era spaziosa e dotata di ogni comfort e divertimento ( kayak, musica ecc). Vasilis e suo figlio Panos sono stati super gentili e disponibili con noi esaudendo qualunque nostro desiderio e preparandoci dei pranzi e delle cene meravigliosi!! ( spesso con pesce pescato da loro sul momento). Grazie Vasilis per aver reso questa vacanza INDIMENTICABILE!
Cpt Vasilis and his son Panos Made our trip a Great experience. The boat was very comfortable and equipped with a lot of amenities ( kayak, Music etc..). Vasilis has always been ready to fulfill our requests to have us enjoy the stay. He’s also a great cook , We had great meals with seafood ( fished by him during the very same trip ) and with other greek specialities.
Thanks so much Vasilis to have Made our vacation so memorable!
An Abbraccio for Riccardo, thanks to you a great cruise in the Cyclades, I am amazed, the wind, a beautiful Aegean Sea with Filippo too, all well the navigation, the table, the company. See you soon, I hope.
I lived 2 extraordinary weeks aboard Riccardo's boat, The 1st week we sailed from Mykonos to Santorini, full of stops in fantastic places, whether coves or ports. I left alone but from the 1st day with the Crew I had no problems. Thanks again Riccardo and GOOD WIND:)
An extraordinary week sailing with Christopher and Marie
Nice welcome extra swimming course in beautiful coves
Good music in the evening and delicious meal
What a good time
Adam and Allan took their first sailing course with Captain Christopher
Do not hesitate to embark
Thank you a thousand times
Adam Allan Zena and Patrick
We have just traveled for a week with Captain Vardis on his boat through the islands of the Cyclades. It was one of the most beautiful experiences, both maritime and the meeting with this superb skipper. We shared many moments of joy, laughter, fun, sailing under the Sun of the Aegean Sea. He made us discover Greece like never before, as well as its very good meals. Enthusiastic, professional, connoisseur of the sea, coves where to swim in this sea of a typical blue, we can only highly recommend it! Thank you again Captain and see you soon, I hope!
What a sailors! Vasilis and his son Panos have been amazing in hosting us and guiding us across the Cyclades. They are real sea dog who has sailed the seas for decades. We have been navigating in full security and comfort across 3000 nautical miles even if sometimes wind and current were against us. Vasilis and Panos have always been attentive to our needs and willing to discuss any itinerary decision. They took us to unique islands snorkeling and spearfishing spots, beautiful beaches with natural hot springs, idyllic white villages. All of their three vessels fleet are fully equipped and comfortable for long cruises, including rigid sun protection structure, SUPs, kayaks, fins and masks, spearguns. Furthermore he is great chef: don't miss his Kakavia fish soup! I had such a great sea-life experience that I can only give my best recommendation to this Ikarian crew. I would jump on board of their boats tomorrow!
Unforgettable holiday with a skipper of rare experience and sympathy! Massimo made us sail between some islands of breathtaking beauty: a holiday that combined the possibility of seeing beautiful coves with a good dose of fun, laughter and good food.
I recommend Massimo as a skipper especially for those who want to live the sailboat at 360 ° combining the desire for a holiday with that of "learning" to experience the sea from another perspective. Massimo's passion for sailing and the sea has been transmitted to the whole crew since the first crossing.
I would recommend Massimo 200% and we will definitely return aboard his fantastic boat for new adventures and crossings together.
Good wind dear Skipper and thank you very much for the beautiful experience!
A beautiful week on the boat
Beautiful itinerary and prepared to the fullest
Pierluigi was an indisputable captain but also ready to have fun with us
With Nicoletta they made the week very pleasant ... just a flaw: it passed too quickly.
Watching Luigi was watching a master at work. He n is an expert sailor and also as a gernerous caretaker of the guests. He goes beyond to ensure that everyone feels welcome, is enjoying the experience and works tirelessly without letting it show to build camaraderie and good will.
I will always remember the crystal clear waters the rhythm of the waves, the laughter of the new friends. A true gift to be on the Grail.
8 reasons to choose the Cyclades for your next sailing holiday:
Home to some of the most spectacular beauty in the Greek Isles in Santorini, Mykonos, and Ios
Lesser-known treasures of the Cyclades such as Sifnos, Koufonisia, and Amorgos which are regarded by expert skippers as some of the most perfect Greek islands
An ideal climate for sailing from April through to October
Learn the special sirtaki dance in the area’s street festivals
Taste the popular Greek liquor, ouzo, with a meal of local produce
Discover some of the world’s most charming coves and lagoons
Immerse yourself in the regions iconic white, cubic architecture and charming fishing villages
The best places & specific destinations to visit during your sailing holidays in the Cyclades:
Sailing the world renowned landscapes of Mykonos
This island of Mykonos, a favourite holidaying spot, is recognised for the beauty of its hilly landscapes, sandy beaches, and picturesque Cycladic white country chapels. Where as, the crescent-shaped Santorini, or Thira, as it’s otherwise known, is in fact a group of islands in the southern Cyclades.
The volcanic complex of the Santorini Islands has crafted some of the most unique arrangements of rock and ocean - while sunset images from the famous Caldera have become synonymous with romance. Then there is the island of Ios, known as Nios by the locals, and considered by many as one of the most beautiful islands in the Cyclades. The Panayia Gremiótissa church that stands at the highest point of Ios offers a striking view over the town and out onto the open sea.
Exploring the secret beauty of the Cyclades
The best kept secrets of the Cyclades are the islands of Sifnos, Koufonisia, and Amorgos. Sifnos with its red bougainvillea that hugs the white of the buildings, as the gentle Meltemi breeze flows over the hills and onto coastline. Koufonisa is said to compete with the best of Greek islands on all fronts. The port of Koufonisa sits on the islands only village, here some of the most charming blue lagoons are being secluded. Amorgos rises dramatically from the Aegean, creating extremely unique landscapes, and is described by skippers as a charm that you most confront at least once in your life.
The Cyclades, which originates from the Greek word for ring or circle, is in fact made up of around 220 different islands. This variety in island, partnered with the Meltemi winds, make for some of the best conditions for a sailing holiday full of discovery and fun.
Tips to help you to better plan for your next sailing holidays in the Cyclades:
As the region boasts a warm climate for much of the year, sailing the Cyclades is recommended between early April and late October.
You can find experiences for a week in the Cyclades with a skipper from €500 per person. This figure excludes transport to and from the holiday. It is important to remember that depending on the month of travel and style of boat pricing is subject to change.
The two main airports in the area are based in Mykonos and Santorini. If not clear in the holiday listing, reach out to a holiday’s organising skipper to understand more precisely the most suitable transport options.
The best sailing holiday itineraries for your next adventure in the Cyclades with a skipper:
Due to the Cyclades having approximately 220 islands, there are a great number of different sailing holiday itinerary options. Popular itineraries include the exploration of some of the areas most popular islands including - Sifnos, Poliegos, Kimolos, Milos, Paros, Syros, Santorini, and Mykonos.
Such concentration of different islands means that some skippers like to propose visiting a new island each day. If there are shorter holiday time frames available, there are many itineraries that revolve more heavily on the Small (otherwise known as Little, Minor or Lesser) Cyclades.
