Yacht sailing holidays & skippered tours in Greece
The Greek Archipelago has over 16,000 km of coastline, with many
beaches that run for kilometres, a host of secluded bays and coves,
and a rich variety of wildlife. Some say the best sailing waters in
the world can be found in Greece!
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Reviews - Yacht sailing holidays & skippered tours in Greece
Matteo is a super Skipper! He is very prepared, he loves his work and is able to communicate this love to the crew, towards whom he is generous with teachings! But that's not all! Matteo is also a beautiful soul! Solar, communicative, chatty at the right time, silent when the sea asks for listening, able to relate to the crew! Last but not least: Matteo gets involved together with his crew, while maintaining his fundamental role and ... Opens the prosecco sabre! In short... Matthew wins!
Andrea and Kikka made our cruise unforgettable! Andrea is a great commander and with his thirty years of experience he entertained us with the stories of his many crossings and gave us a navigation with many sailings always in maximum safety making our experience exciting.
Kikka pampered us with the onboard kitchen. Thanks to his expertise he taught us the rudiments of sailing and gently complied with our every need. I will definitely do other cruises with them.
Our week aboard Mattia46 was beautiful. Umberto guided us with competence and sympathy to discover corners of the Dodecanese where we could do everything that was in our expectations: long swims, beautiful walks and delicious eats! Elisa spoiled us with a healthy and tasty cuisine, Nicholas tomatoes for us have become legend. The boat is very comfortable and is equipped with practically every comfort, we have experienced all the beauty of sailing without being forced into narrow spaces. The desalinator was then a real gem. All this was combined with extraordinary travel companions, with whom we immediately formed (and until the end) a compact and cheerful crew.
Great and skilled skipper who is focussed on teaching sailing, building group confidence and communication and experiencing nature. A great alternative to party tourism and luxury cruises - we stayed in wild bays for 6 nights which was extremely relaxing! I started from a level of no experience whatsoever and learned a lot while enjoying the stunning landscape of the Ionian Islands. Emmanuelle was very attentive and flexible to our needs and ideas for the route and also a great company for the trip! It was also particularly amazing as a non-male person to travel with a female skipper of whom there are too few! Highly recommended, already looking forward to our next trip.
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.
Excellent stay with Sabine and Patrick around the Ionian Islands.
They are very accommodating and will do their best to make you have the best possible stay according to your desires.
Go there with your eyes closed!
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!
ON HOLIDAY WITH A SPECIAL PERSON
My holiday with Davide was a nice holiday.
The boat is wide and comfortable. The skipper a special person, sailor, chef, man of the world, a friend...
The cruise was pleasant even if there was little wind in the area so mainly motorized. The places, especially PAXOS and ANTIPAXOS very nice. We traveled in a group of three boats for which the company was not lacking. Every day for lunch a Greek or Neapolitan dish cooked with skill.
What can I say? I recommend it.
There would be so much to say but I will be short and engraved: the captain the skipper indeed both multipurpose 2Shores careful you have needs and the protection of the crew.
2 excellent cooks other than to be 2 cultured and very pleasant people . Thanks hard not to get attached .
Silvia
We had a fantastic sailing week exploring the Northern Sicily and Eolian Islands Lipari and Volcano with Frizzante. Mark is a competent and professional skipper. The ambience in the shipshape boat is forthcoming and relaxed. We enjoyed good food, music and sailing. Happily recommended!
Hello
We had the pleasure of sailing with Alessandro. He is a very friendly boy who was very caring for us. Always wondering if everything was okay and if we needed anything. He knows the island of Corfu and its history very well. The meals prepared by himself, of local types were delicious. In addition we had the chance to be accompanied by his brother Andrea who usually pilots another boat and who is older and just as pleasant as his brother. We spent a very nice week in their company and are thinking of renewing the experience at a more summer time to enjoy swimming. I highly recommend this mini cruise especially with these two young people in love with nature, the sea and their job as sailors because we feel that it is really a passion for them.
Raffa is the perfect skipper! Calm, never too intrusive or over the top, in short, in the meantime it transmits tranquility and confidence, which on the boat - especially for those who are at the first experience - is important. As soon as I saw it seemed to me the dj Luca Agnelli, oh well just a little lower ????. He is a sunny and sociable person, with whom you can talk about everything and it was nice to enter his world. He never shied away from partying with the crew at any time, with the excuse that he went out of his way to keep us entertained. Raffa, made us discover some wonderful coves. In short, I recommend him, for that calm madness of his.
Expert skipper, great historical, political and social culture of Greece. He knows all the excellences present in the territory, a great connoisseur of wines and typical foods. Great cook and organizer. He was a great colleague for organizing holidays out of standard.
In mid-September, organized last minut, Agata and I embarked on a Bari-Kos and after three days spent knowing the most beautiful places in Kos, on Sailsquare we found the opportunity to embark with Stefano in Patmos. Taken the first fast catamaran from Kos in a couple of hours we were in Patmos embarked with Stefano. We spent four days between Ptmos, Arckì, Lipso and Leros, almost always sailing in the most beautiful places and beaches thanks to Stefano with his experience as a skipper and life on his 15 meters of 1989 but in perfect condition.
On the boat there were only three of us, Stefano and the two of us and when we had to disembark to reach Kos by ferry and not sailing because of a wind at 30 knots and not quiet sea a tear united us in the greetings.
Thank you Stefano for giving us these 4 unforgettable days, with your tranquility and availability as if we were friends forever.
We will come back very soon.
If you are looking for a holiday that combines fun, adventure, relaxation and new friendships you have found what is right for you! My girlfriend and I boarded without knowing anyone from the crew and it was amazing. We got to make some great friends and have a lot of fun. The skipper was great! He took us to heavenly places and proved to be extremely helpful in all kinds of situations. During the day we moved to different places to swim and visit beautiful islands, while in the evening we usually ate in very special taverns. Good food and company made the evenings magnificent! I honestly recommend everyone to try such an experience! You will probably stop spending your holidays on crowded beaches to prefer the boat even in the following years. As already mentioned, the skipper was amazing and contributed a lot to making the holiday perfect! Thank you very much :) :) :)
Mattia is the best skipper with whom I have ever sailed: always very attentive and scrupulous with a great sense of responsibility and passion for sailing, despite there have been moments of sea and strong wind I have always felt calm. He is always in a good mood (amazing) and working to plan the perfect day for everyone
Beautiful experience, our flotilla was made up of beautiful people, I have made a lot of connection with my boat, an experience that I will definitely do again. I left my comfort areas behind and spent 7 days of adventure, sharing and team spirit. A special thanks to Nicola who was a friend, a brother and a great captain for this week.
Renato is doing his best but at his age it's not that easy anymore (I sincerely think he's - a lot - over 62). The boat is comfortable but would need a facelift, like its captain! help with maneuvers is not easy if you do not understand Italian, because English is succinct. Otherwise nice navigation and meals, nice corners and favorite for Alakka.
Our week on Vincent's catamaran was great!
Vincent is really good captain, with a lot of experience, you can learn a lot if you want - do things on the boat - or not, depends from you. He will explain everything (he also has a groups for sail training). Apart from this, he is a really interesting person with many great stories from his life, really easy going and with good recommendation always. Normally at night you can have a dinner in a restaurant, on your own or go with the captain and the rest of the crew, we always chose the second option, as dinner with them was great and the selection of the place perfect!
Melanie, his partner, was helpful, and funny! You just have great time with her! And a lot of ice-creams :)
The boat is comfortable, and they do not take more than 4 people although there is one cabin unocupied so the group is more comfortable.
The area of Ionian Islands was above our expectations. Wonderful views, really beautiful places with clear water.
I recommend it!!!
The most relaxing trip of my life. If you really need to unplug, without getting bored, a week on a sailboat is for you. Relaxation, rest, contact with nature, music, wind, water, silence, music, colors, adrenaline, good food, sharing, new experiences: find everything. Fabio is an experienced skipper, he knows the area well, he integrates into the group being a very easy-going and nice person; knows how to create beautiful atmospheres. I really think that next year another sailing tour will not hurt me :D
For us it was the first sailing experience. We never expected to live such an intense and unforgettable adventure. In the amazing setting of Ionian Greece we spent an intense and at the same time relaxing holiday between dream beaches and unspoiled islands. Pino was absolutely fabulous, making the experience even more incredible with his sympathy and with his knowledge of the most evocative and fascinating places. He is a person who accompanies us on a journey to discover unknown and mysterious landscapes, flavors and smells.
A superb cruise and a beautiful boat.
A huge thank you especially to Fotis, our skipper for his efficiency, his kindness and his constant efforts to make the whole family spend an exceptional week.
8 reasons to choose Greece for your next sailing holidays:
Excellent sailing conditions throughout the year, with calmer areas and areas for more advanced sailing
Thousands of unique islands to explore, including some of the world’s most beautiful
Delicious local specialties, such as: tzatziki, tarama, moussaka, dolmades, the famous Gyros, and of some of the traditional Greek liquor Ouzo and Raki
Home to some of the most spectacular beauty in the Greek Isles in Santorini, Mykonos, and Ios
Endless sailing itineraries to be designed with your skipper
Immerse yourself in the regions iconic white, cubic architecture and charming fishing villages
Discover some of the world’s most charming coves and lagoons
Learn the special sirtaki dance in the area’s street festivals
The best places & specific destinations to visit during your sailing holiday in Greece:
Famous sailing areas include the Cyclades, the Saronic islands, Ionian islands, Dodecanese, Sporades, and Crete - however, there are an estimated 5,000-6,000 islands in Greece. Travelling the Greek isles by sailboat allows for full exploration of the areas treasures, that would otherwise be inaccessible. Whether you are planning to travel solo, as a couple, with friends or family, and whether you are looking for a sailboat or catamaran experience, there are numerous areas of Greece that make for perfect holidaying destinations.
The variety of sailing in Corfu between coastal town hopping and more open water routes, make it a great destination to gather a well-rounded sailing experience. Surrounding Corfu are some smaller Ionian Islands, with striking beauty and unique wildlife ecosystems - along with the coast of Albania to the north, there is much surrounding the region to explore.
The area is named after the grandson of Greek god Apollo - god of music, art, and the sun - Mykonos is often described as the heart of the Cyclades, and an excellent place to observe some of the richest history and tradition in Greece. Alefkántra or 'Little Venice' in Mykonos' capital town Hóra, is a beautiful example of such history - the 18th district of the town is recognised for its unique architecture, and its relationship with the sea it is perched above.
As a precious jewel of the Aegean, and a place of striking natural beauty, Santorini has become one of the most sort after destinations in Greece. The island is the byproduct of a volcano eruption, which explains the incredibly dramatic views over Oia town, which at sunset is a truly iconic sight to behold. With a collection of golden and red beaches, and natural springs surround the island, exploring the area by island is the only way to truly experience it.
Tips to help you to better plan for your next sailing holidays in Greece:
All you need to know about your next cruise in Greece aboard a sailboat.
When to go to Greece for a sailing holiday
Greece has a pleasant Mediterranean climate throughout the year. The temperatures become particularly pleasant from April until the end of November. The periods of July and August are relatively busy, and travellers may find that in May, June, September and October trip are particularly enjoyable for boarding a sailing or catamaran holiday. The wind is moderate, therefore, you can calmly enjoy the beauty of the islands. If you decide to travel at a busier time of the year, your localised skipper will be able to take you to places tucked away from the masses.
How long should a sailing holiday in Greece be?
The Greek archipelago is vast and it is important to choose the destination according to the available amount of time, so you can fully enjoy the experience without hurry. We recommend a minimum of two weeks to discover the Cyclades and the Dodecanese. If you have less time, we recommend looking at holidays in the Ionian, Saronic, Sporades and Crete.
Transport options to and from your holiday
Greece has many international airports including Athens, Corfu, Kos, and Kefalonia where there are budget airline options. Prices can increase significantly during school holiday periods, mainly summer in July and August. We would recommend going slightly outside of the main season in May, June, September, and October. Greece has a highly developed ferry network that connects the main islands with each other, it might be required that you use one of these ferry routes in order to reach your skipper. Your skipper will be able to advise you on the best flights and additional ferry services that might be necessary.
Sailing holidays in Greece with a family
There are some sailing destinations that are particularly suitable for family holidaying. Greece is one of these destinations. The sailing conditions are ideal and the mooring opportunities are numerous. You will easily find a deserted cove where you can find an anchor spot for the kids to have fun on the beach or shallow waters. Sailing holidays are fun for both young and old!
Sailing holidays in Greece - why you should travel with a local skipper
If you want to fully enjoy your sailing holiday in Greece in the best conditions, we recommend that you go choose a trip with a local skipper. Travelling with a skipper who has insider knowledge on the area, allows travellers to fully immerse in the pleasure and relaxation of the holiday. Where individuals on the trip wish to learn or practice their sailing skills, skippers will be there to integrate travellers into the responsibilities onboard.
The best sailing itineraries for your next holiday with a skipper in Greece
The big Cycladic Tour: For this trip two weeks are needed to explore this archipelago from Athens. The first part of the trip will be to explore the islands of the small Cyclades ( Kea, Siros, Tinos, and Kithnos), before heading to the archipelago of the great Cyclades (Naxos, Milos, Ios, Sifnos, and Amorgos) where there is the option to push up to Santorini. The return can be made directly to the port of Piraeus in Athens, or by first making a detour to the Saronic Islands (such as Hydra).
Cruise around the minor Cyclades: a very beautiful adventure, and ideal for a week or more away from the powerful Meltem that can blow during the summer months in the great Cyclades. From Athens, you could then consider exploring the beautiful Kea, Siros, Tinos, Kythnos and Serifos.
Discover the Ionian Islands and the Sea of Ulysses: a wild and untouched archipelago that is ideal for a week of relaxation. Fiscardo, the white cliffs northwest of Ithaca, the beautiful village of Kioni and its beautiful bay, the isolated island of Atokos without forgetting to stop by Kalamos and Kastos. Lefkada is then not too far away with a final well-deserved stopover before arriving to the charming port of Sami in Kefalonia.
The beautiful islands of northern Corfu: get ready for an extraordinary adventure exploring the islands of Mathraki, Erikoussa and Othonoi. Deserted beaches, very few inhabited islands, splendid moorings - a destination perfect for a holiday made of serenity.
The magical journey to Saronic Islands sailing from Athens: a splendid region sheltered from the wind and waves for calm and pleasant island hopping. From Athens, the first step can be Hydra (famously, the island without a car). After a hike ini Leonidio, you can then reach the islands of Dokos for a BBQ on the beach at Poros, and end the voyage with a cultural stopover in Epidaurus.
Exploration of the Sporades: with a week at sea aboard a sailboat, you are sure to uncover some of the wonders of the Sporades. Let yourself be carried by the wind to the islands of Skiathos, Skopelos, Alonissos, Kyra Panagia, and Peristera.
Discovering the Dodecanese: From the island of Rhodes (the largest of the archipelago), embark on a wild sailing holiday with changing sceneries. On the agenda: hopping along the Turkish coast to reach the ruins of Bouzoukale and the charming village of Bosborum, visiting the island of Symi, the Datca Peninsula and the small port of Palamut. Finally, the island of Nisyros and its volcano make for an excellent last stop before heading back to Rhodes.
