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      • WWF Sailing Cruises
      • Whole boat with skipper
      • All inclusive
      • Crewed
      • Catamaran
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Yacht sailing holidays & skippered tours in Greece

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!

  • Sailing Holidays
  • Greece

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 39 reviews
    confirmed

    Cyclades and Microcicladi on a magnificent 15-meter boat

    from 4 June - 7 nights
    Cyclades Greece
    2 people interested
    in this holiday
    636€ Per person
  • 41 reviews
    confirmed

    From Lavrion to Mykonos. The Western Cyclades seen in the most beautiful period

    from 4 June - 7 nights
    Cyclades Greece
    4 people
    are onboard
    777€ Per person
  • 20 reviews
    confirmed

    Ready to set sail? ... prepare your bags and we'll take care of everything else! .. Magical places await you - Hostess on board

    from 4 June - 7 nights
    Ionian Islands Greece
    3 people
    are onboard
    667€ Per person
  • 1 review
    almost
    confirmed

    Are you a lover of nature and crystalline seas? This is the perfect relaxing holiday

    from 4 June - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    545€ Per person
  • 17 reviews
    almost
    confirmed

    By sailboat to discover the Dodecanese

    from 4 June - 7 nights
    Dodecanese Greece
    Join in on this experience!
    583 530€ Per person
  • 33 reviews
    almost
    confirmed

    Sailing holiday between the Saronic islands

    from 4 June - 7 nights
    Saronic Islands and Athens area Greece
    1 person interested
    in this holiday
    732€ Per person
  • confirmed

    Set off to discover the Ionian islands with the gastronomy of Davide, your skipper cook!

    from 4 June - 7 nights
    Ionian Islands Greece
    1 person
    is on board
    636€ Per person
  • 21 reviews
    confirmed

    Cruise in the Cyclades: from Milos to Mykonos

    from 4 June - 7 nights
    Cyclades Greece
    4 people
    are onboard
    499€ Per person
  • 18 reviews
    almost
    confirmed

    Sail with us under the Greek sun in its paradise islands

    from 4 June - 6 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    583 530€ Per person
  • 4 discounted
    spots

    Active Sailing Week around Cyclades

    from 5 June - 7 nights
    Cyclades Greece
    2 people interested
    in this holiday
    580 521€ Per person
  • almost
    confirmed

    Zante - Milos

    from 6 June - 13 nights
    Cyclades Greece
    2 people interested
    in this holiday
    1.166 1.134€ Per person
  • 32 reviews
    confirmed

    All Inclusive cruise to the Ionian Islands with hostess. Relax, we'll take care of the rest!

    from 6 June - 6 nights
    Ionian Islands Greece
    2 people
    are onboard
    810€ Per person
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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 Greece

1229 reviews
20 / 10
Eeva V.

Eeva V.

review about May Bank Holiday from Corfu to Sicily, sea, sun and wind all for you! April 2022

10 / 10
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!
Norbert M.

Norbert M.

review about Are you a lover of nature and crystalline seas? This is the perfect relaxing holiday April 2022

10 / 10
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.
Caterina G.

Caterina G.

review about Sun & Fun Marmaglia Flotilla - 5 Boats in Ionian Greece August 2021

10 / 10
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.
Leo L.

Leo L.

review about In the sea of Ulysses with the sport you want! August 2021

10 / 10
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.
Pietro P.

Pietro P.

review about Stroll around the Dodecanese on a 15m boat - boarding in Kos or Leros September 2021

10 / 10
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.
Silvia A.

Silvia A.

review about Sailing in the footsteps of Ulysses! 7 days to discover the Ionian islands with hostess on board September 2021

8 / 10
Great nice holiday! Splendid itinerary with stops in quiet coves and crystal clear sea. Relaxing holiday on a large and very comfortable boat!
Jacques-Daniel B.

Jacques-Daniel B.

review about 10 days of pure relaxation and comfort in the Dodecanese (1st Round) August 2021

10 / 10
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 :) :) :)
Sveva C.

Sveva C.

review about On the route of Ulysses sailing! Ithaca, Zakynthos, Kefalonia in a splendid Oceanis 46.1 of 2020 !! August 2021

10 / 10
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
Luca F.

Luca F.

review about CRAZYSAIL GREECE - 4 boats to the Saronic islands August 2021

10 / 10
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.
Antoine P.

Antoine P.

review about Surf live east! Galley included on board! August 2021

6 / 10
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.
Aleksandra K.

Aleksandra K.

review about By catamaran in the heart of the Ionian Islands July 2021

10 / 10
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!!!
Roberta C.

Roberta C.

review about Visit the islands of Greece with a beautiful boat and the experience of those who have lived there for years! July 2021

10 / 10
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
Claudio P.

Claudio P.

review about The Greece of the myth on a sailing boat. July 2021

10 / 10
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.
Stéphane T.

Stéphane T.

review about SHARE & SAIL: explore Cyclades with new friends July 2021

10 / 10
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.
Luc B.

Luc B.

review about Unique Sailing Vacation September 2020

10 / 10
Excellent navigator and sailor knowing the area perfectly. From +, he spoke good English. Good boat very clean and comfortable despite the small size of the cabin. He always offered us great little restaurants and helped us visit the islands of Skiathos and Skopelos We plan to return to Greece and sail with Lambros.
Aleksander D.

Aleksander D.

review about Where the Meltemi blows. The charm of Patmos, Leros, Lispi, Levita and Kalimnos. August 2020

10 / 10
Guido is an experienced skipper that leaves no room for surprises. He's fully proficient using sailing apps for navigation and weather forecast to plan routes and happy to share its knowledge with the crew. He's keeping the boat in immaculate condition for the crew to fully enjoy the time onboard and the sailing experience. I'm happy to have met Guido and the rest of the crew on this occasion and would be more than happy to book sailing with him again.
Federico G.

Federico G.

review about In the footsteps of Ulysses ... August 2020

10 / 10
Exceptional holiday! We visited everything you could see, the boat is very comfortable and has everything you need. Stéphane was very kind, very nice and with a great knowledge of the place. I particularly enjoyed the formula with breakfast and lunch included. The price was a bargain.
Lydia M.

Lydia M.

review about 4 day sailing adventure! Max 6 guests in 8 berths.This year travel in comfort & avoid the crowds August 2020

10 / 10
Adrianna and Radu are the hardest working team on the islands and their goal is to figure out exactly what you want from your sailing vacation and provide it. They were sensitive to what we were looking for- local/ insider sights, some nightlife, the best spots for snorkeling and paddle-boarding, and have great recommendations about what to do and see at each port. Quad biking on Kythnos is a must! They were super informative and helpful from my first enquiries until the day we left. I and my travel buddy will be back for sure!
Claudia G.

Claudia G.

review about By boat between Kefalonia Ithaca and Zakynthos August 2020

10 / 10
What can I say? Gianfranco is an exceptional captain with great experience, a real sea wolf, an excellent skipper, a perfect chef and a good Romagna jovial and very hospitable person. His boat is absolutely comfortable, spacious and well maintained...... and then there is the crystal clear sea that is the master. Good wind!!!
Devon C.

Devon C.

review about Premium one way sailing trip - taste BOTH the Saronic AND Cyclades islands. From Paros to Athens August 2020

10 / 10
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
Luca P.

Luca P.

review about Ulysses' course, August 2020

10 / 10
Skipper and catamaran Top, equipped with every good of god... Sup, canoe, diving equipment etc ... Fabio in addition to an excellent preparation is very good at teaching a little sailing to those interested, it seems strange, but in Charter it is a rare thing. Recommended for those who want to spend a week of relaxation in the name of sea sailing and lots of nature. Do not forget the cute Jack, the delicious sailor dog, always looking to be pampered by everyone, the mascot of the boat!
Maurizio M.

Maurizio M.

review about Are you a lover of nature and crystal clear seas? JOIN US !!! ZERO STRESS, INCLUDED HOSTESS July 2020

10 / 10
Susanna Andrea a perfect copy . Great service and hospitality.... magnificent places
Laurence H.

Laurence H.

review about Sailing course in the Cyclades July 2020

10 / 10
Sylvain is an excellent Skipper always in a good mood and sovereign who has sailed around the world for 4 years and 1/2. So everything seems easy acec him. Even brave the Meltemi. Genial with teens. My 15-year-old son loves to steer, work with sails and go outboarding. A magnificent experience in landscapes of dreams.
Brigitte S.

Brigitte S.

review about Relaxing Cruise sailing from Milos volcanic to beautiful Cyclades Minor September 2019

10 / 10
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.
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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.

Sailing holidays in Corfu

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.

Sailing holidays in Mykonos

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.

Sailing holidays in Santorini

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.

Greece: the most beautiful places to sail

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Greece: next departures

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Greece: best travel ideas

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  • France
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  • Croatia
  • Spain
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  • The Balearic Islands
  • Gulf of Naples
  • Split Archipelago
  • Southern Sardinia
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  • French Riviera and Porquerolles
  • Saronic Islands and Athens area
  • Amalfi Coast
  • Corsica
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  • Grenadines & Martinique
  • Canary Islands
  • Brittany and Normandy
  • Sicily
  • Venice and the Gulf of Trieste
  • Guadeloupe
  • The Maldives

Top Travel Ideas

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  • All inclusive
  • Crewed
  • WWF Sailing Cruises
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