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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!

  • confirmed

    Discover the Ionian Islands from Zante on a beautiful Caicco - Breakfast and lunch included

    from 6 May - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    747€ Per person
  • 3 reviews
    3 discounted
    spots

    Sailing cruise in the Greek Islands - Saronic

    from 6 May - 7 nights
    Saronic Islands and Athens area Greece
    2 people interested
    in this holiday
    530 508€ Per person
  • 18 reviews
    3 discounted
    spots

    Gone with the wind, Termoli-Lefkada 3rd step Corfu-Lefkada

    from 6 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    416 400€ Per person
  • 5 reviews
    4 discounted
    spots

    Didactic week on a sailing boat Ionian Greece

    from 7 May - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    901 863€ Per person
  • 1 review
    confirmed

    A week of sailing in the Cyclades on an exceptional sailboat

    from 10 May - 7 nights
    Cyclades Greece
    2 people
    are onboard
    1.108€ Per person
  • 2 discounted
    spots

    Sailing trip in Greece: from the Cyclades to the Peloponnese and to the Island of Kythera

    from 12 May - 9 nights
    Peloponnese Greece
    Join in on this experience!
    901 848€ Per person
  • 5 reviews

    Sailing to Sporades with the Amazing Hanse 54e and local Skipper

    from 13 May - 7 nights
    Sporades Greece
    Join in on this experience!
    851€ Per person
  • 22 reviews
    almost
    confirmed

    Cruise to LEFKADA, ITHAKI, MEGANISI, KALAMOS and ATOKOS

    from 13 May - 6 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    583€ Per person
  • 2 reviews
    confirmed

    7 days of SAILING/YOGA & SUP in CYCLADES GREECE

    from 13 May - 7 nights
    Cyclades Greece
    2 people interested
    in this holiday
    790€ Per person
  • 29 reviews
    almost
    confirmed

    Ready to set sail? Magical places await you! - HOSTESSES on board

    from 13 May - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    550€ Per person
  • Sporades Islands: Sailing holidays are more than just holidays!

    from 13 May - 7 nights
    Sporades Greece
    Join in on this experience!
    880€ Per person
  • 32 reviews
    almost
    confirmed

    Sailing Didactic Course in the Dodecanese

    from 13 May - 7 nights
    Dodecanese Greece
    Join in on this experience!
    769€ Per person
  • 1
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Reviews - Yacht sailing holidays & skippered tours in Greece

1416 reviews
20 / 10
Patrick M.

Patrick M.

review about Sailing cruise in the Greek Islands - Saronic August 2022

10 / 10
If you are looking for a dream cruise, on a high-performance and very well maintained boat, with a nice skipper, pedagogue and full of humor (and not only Belgian), who knows how to create a link in the crew, find the right little restaurants in the ports, accompany you on hikes to see the sunset, do not hesitate, Bertrand's cruises are for you. And I tell him see you soon for a new adventure. Patrick
Ugo P.

Ugo P.

review about 7 days of sailing SUP & snorkeling in Cyclades Greece August 2022

10 / 10
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.
Guido  V.

Guido V.

review about The route of the Gods July 2022

8 / 10
Beautiful experience, with Marco you will be in expert and safe hands as well as being an absolutely pleasant travel companion. Highly recommend.
Anna G.

Anna G.

review about LAST MINUTE! CRAZYSAIL GREECE - 7 boats to the Saronic Islands - LAST PLACES FOR WOMEN August 2022

10 / 10
Agata was the skipper of my first sailing holiday and I couldn't get better, passionate, professional and full of energy, a wonderful soul!
Matteo Q.

Matteo Q.

review about LAST MINUTE OFFER! - CRAZYSAIL GREECE - 4 boats to the Saronic islands August 2022

10 / 10
I had sensed Luca's potential as a skipper already at the Academy and the first week of the CrazySail Greece sailing experience was the confirmation I was waiting for. I am extremely proud to be part of the path luca has made and the results he has achieved. Despite various difficulties that he had to face, starting from the aftermath of Meltemi, up to the broken anchor sail, he managed not only to get out of it with his head held high at a technical level, but also not to make his crew weigh the unexpected situations, keeping morale high, the smile on everyone's lips and a strong desire to sail and party. Luca deserves a special mention for landing in Hydra, a very busy and difficult port, which often even the most prepared skippers avoid like the plague. He managed the mooring masterfully, giving his crew the opportunity to enjoy a fantastic day on the island. Great job, Luca and good wind for the future!
Matteo Q.

Matteo Q.

review about LAST MINUTE OFFER! - CRAZYSAIL GREECE - 4 boats to the Saronic islands August 2022

10 / 10
Isa is definitely the skipper for whom I have the most esteem and admiration of the whole CrazySail flotilla. She had already distinguished herself during the Academy, but it was during the first week of CrazySail Greece that she really showed her qualities. Despite my young age, I don't know any other person I would blindly rely on for technical skills and crew management. He led his crew during a week-long sailing experience in the Saronic Islands, with Meltemi aftermath, wind at 28-30 knots, gusty 35. Impeccable both in sailing and in port and raft maneuvers, having Isa as a skipper is an opportunity for all those who want to approach sailing and also for those more experienced. I am obliged to a special mention for how he managed the mooring in the port of Hydra, a well-known marina very busy and very difficult to approach, which many skippers even with more experience, avoid like the plague. Good wind, Isa!
Matteo Q.

Matteo Q.

review about LAST MINUTE! CRAZYSAIL GREECE - 7 boats to the Saronic Islands - LAST PLACES FOR WOMEN August 2022

10 / 10
I met Simone on a sailing boat and immediately there was a great understanding between us, which led us to consolidate a strong friendship, born from the common passion for the sea and sailing, as well as from the sharing of the same ideals. Simone is an excellent skipper, capable both at a technical level and at the level of crew management. You spend completely to give your crew strong emotions, as only sailing can do. In navigation with him you will feel safe in all weather and even where many skippers tend to "slip", that is, the maneuvers in port, Simone knows how to face them calmly and lucidly, thanks to the years of experience gained. I would like to recommend it to the entire Sailsquare Community; having him as a skipper will be an honor and a privilege and you will not regret it.
Andrea D.

Andrea D.

review about From Kos to Patmos to discover the Dodecanese islands August 2022

10 / 10
Max is a fantastic captain: among his qualities immediately stand out an extreme kindness and the willingness to meet all the requests of the crew, finding those solutions that make everyone agree and allow you to navigate in complete safety. Recommended for those looking for a holiday full of exploration and fun: his knowledge of the coves in which to dive and his ability to involve everyone in the evenings of celebration are exceptional, such as to make me return home really happy for the moments lived on vacation and with a phrase perhaps pronounced too low in a voice when I greeted him on the day of departure: THANKS MAX!
Gabriella D.

Gabriella D.

review about LAST MINUTE OFFER! - CRAZYSAIL GREECE - 4 boats to the Saronic islands August 2022

10 / 10
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!
Stefania A.

Stefania A.

review about Sailing cruise to the Ionian Islands August 2022

10 / 10
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.
Angelo D.

Angelo D.

review about Coastal navigation suitable for all those who are eager to experience sailing. July 2022

10 / 10
Our week aboard Umberto's boat 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.
Germano A.

Germano A.

review about Ionian Greece sailing in absolute relaxation with all comforts July 2022

8 / 10
I would say it was a beautiful holiday, all expectations were met. Maurizio is definitely a great example of Skipper!
Isabel B.

Isabel B.

review about Sailing course and discovery of Ulysses' Greece - Ionian Islands July 2022

10 / 10
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.
Silvia C.

Silvia C.

review about Adventurous Pirates exploring the Cyclades Islands! July 2022

10 / 10
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.
Pierre S.

Pierre S.

review about Sail with us under the Greek sun in its paradise islands July 2022

10 / 10
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!
Giovanna C.

Giovanna C.

review about Paros-Small Cyclades-Amorgos June 2022

10 / 10
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!
Stefano S.

Stefano S.

review about Set off to discover the Ionian islands with the gastronomy of Davide, your skipper cook! June 2022

8 / 10
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.
Silvia V.

Silvia V.

review about All Inclusive cruise to the Ionian Islands with hostess. Relax, we'll take care of the rest! June 2022

10 / 10
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
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. 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.
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!
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.
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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: best travel ideas

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  • The Balearic Islands
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  • Sicily
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  • Split Archipelago
  • Grenadines & Martinique
  • French Polynesia
  • Dodecanese
  • Brittany and Normandy
  • The Maldives
  • Saronic Islands and Athens area
  • Guadeloupe
  • Corsica
  • Canary Islands

Top Travel Ideas

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  • Monohull
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  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
  • Crewed
  • WWF Sailing Cruises
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