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      • All Greece
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      • French Riviera and Porquerolles
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      • Split Archipelago
      • Kornati Islands
      • Turkey
      • French Polynesia
      • Norway
      • Adventure
      • Courses & regatta
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      • Flotilla
      • Offshore
      • Sport & wellness
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      • Whole boat with skipper
      • All inclusive
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Crewed yacht sailing holidays & tours in Greece

Crewed yacht sailing holidays & tours in Greece

Get on board on a crewed sailing holiday in Greece for the most relaxed time ever.

  • Sailing Holidays
  • Greece
  • Crewed

FLEXIBLE CANCELLATION.

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

  • 34 reviews
    4 discounted
    spots

    Sailing holiday from Lefkas to Kefalonia, Zante and Itaca - on maxiyacht with Chef

    from 4 March - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    1.039 986€ Per person
  • 9 reviews
    almost
    confirmed

    Pack your suitcase and we'll take care of the rest! Steward aboard!

    from 1 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    451€ Per person
  • 29 reviews
    almost
    confirmed

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

    from 1 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    451€ Per person
  • 9 reviews
    almost
    confirmed

    Pack your suitcase and we'll take care of the rest! Stewart aboard!

    from 8 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    462€ Per person
  • 29 reviews
    almost
    confirmed

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

    from 8 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    462€ Per person
  • 34 reviews
    5 discounted
    spots

    Cabin charter Cicladi, From SANTORINI to MILOS E SIFNOS SU UN MAXIYACHT - Chef a bord

    from 8 April - 7 nights
    Cyclades Greece
    Join in on this experience!
    1.219 1.166€ Per person
  • 9 reviews
    almost
    confirmed

    Pack your suitcase and we'll take care of the rest! Stewards on board!

    from 15 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    483€ Per person
  • 29 reviews
    almost
    confirmed

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

    from 15 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    483€ Per person
  • 9 reviews
    almost
    confirmed

    Pack your suitcase and we'll take care of the rest! steward on board!

    from 22 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    462€ Per person
  • 29 reviews
    almost
    confirmed

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

    from 22 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    493€ Per person
  • 9 reviews
    almost
    confirmed

    Pack your suitcase and we'll take care of the rest! steward on board!

    from 29 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    488€ Per person
  • 29 reviews
    almost
    confirmed

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

    from 29 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    483€ 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 - Crewed yacht sailing holidays & tours in Greece

102 reviews
20 / 10
Carla A.

Carla A.

review about Exploring Ionian Greece and Salento - Hostess on board - Embarkation and disembarkation in LEUCA August 2022

10 / 10
I have just returned from my holiday with Gianni to the Ionian islands of Greece. What can I say? He and Giovanna were wonderful. Gianni is a true connoisseur of the sea. Together with my travel companions we lived an experience of joy and safety. He made us discover lovely places with joy and availability. He and Giovanna cooked for us, accompanied us on excursions and we also learned a few more secrets about the winds and navigation. Giovanna amazing! Goliardic and playful climate always. I recommend to everyone!
Lorena S.

Lorena S.

review about Ready to set sail? ... prepare your bags and we'll take care of everything else! .. Magical places await you - Hostess on board June 2022

10 / 10
With Andrea in first place, competence and safety at sea. From a human point of view a very special person for the attention he has towards his guests and the ability to better cope with any situation or request. A beautiful week of carefree and fun. Thanks to him and his collaborators, Alessandro and Susanna, see you soon guys!!
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
Sébastien R.

Sébastien R.

review about One way Cyclades with experienced captain and amazing food :) September 2021

10 / 10
A week spent aborad the ZORBA with Captain Greg & Aga... and what a week ! :-) A warm welcome, a cruise oriented customer satisfaction while being responsive to the weather forecast while ensuring safety, a professionalism to explain the conditions of navigation, guides to discover the best spots of the Cyclades and typical local restaurants. But especially two people TOP! Two apathic people, playful, plaisant, patient and who take the time for each one. A week with 10 polish people who have all made the effort to speak english to integrate me in their discussions and create a real exchange on board. I can only recommend Greg & Aga! :-)
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!
Tiberghien T.

Tiberghien T.

review about The enchanted sea of the Ionian Islands - Hostess on board July 2021

10 / 10
a wonderful week in excellent company, thank youIiii Omar and Erinca always taking care of us, on a perfectly maintained boat. And their desire to make us discover wonderful places, accompanied by excellent Italian recipes. A constant good mood. La Bella Vita :) We all loved it. Again Merciiii Captain and his wonderful Cambusiere Clotilde , Thomas , Jules , Baptiste and Sébastien-Martin
Africa S.

Africa S.

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

10 / 10
Perfect holidays! :) We had a great time! Thanks to capitain Georgis & George for this awesome experience. It was a very well organized trip, the best way to explore the Cycladas islands sharing with a great group of people. We felt very safe with Georgis, our capitain (the best one!) was always looking for the wellbeing of the group and he was adapting our stops depending on the weather to make the most of every single place. We loved and enjoyed all the places he suggested. We will repeat for sure! Thanks again!
Marino S.

Marino S.

review about Circumnavigating Corfu on the Feaci routes - Hostess on board! August 2020

10 / 10
we did not leave for the holiday (by our choice) by virtue of all the uncertainties related above all to the procedures of return from Greece for covid, but a review on Hansel I would like to do anyway: correct, courteous and available from the beginning to look for and propose solutions that could facilitate the holiday despite the climate of uncertainty. He is a person who makes you feel calm from before departure. Something to complain about Sailsquare and its policies that are too strict in a situation like this.
Céline V.

Céline V.

review about From Mikonos to Poros aboard a Lagoon 400 catamaran August 2020

10 / 10
It was a real pleasure to sail with François and Isabelle! Super nice couple, very good atmosphere on the boat. François was able to adapt to our pace without worries, offering great coves and itineraries every day. Idyllic holiday setting, super comfortable catamaran. To do again next summer!!
Debora C.

Debora C.

review about All inclusive! Embark and enjoy the Ionian islands .... we'll take care of the rest! August 2020

10 / 10
They are two fantastic characters! Their kindness and sympathy is beyond imagination... what about the boat a dream that sails!!!!
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
Paul D.

Paul D.

review about Relaxing Cruise sailing from Milos volcanic to beautiful Cyclades Minor July 2020

10 / 10
We had an amazing time with Nikos and his sister who joined for this trip, both were very experienced skippers and extremely attentive as well as being very knowledgeable about the places we visited. The schedule was flexible and adjusted to the according to our interests. The 4 day trip was very relaxing and highly recommended for anyone who wants to cruise the Cyclades. The yacht is well equipped and comfortable and the food being served was delicious! We have such great memories which we will cherish forever!
Fiorella C.

Fiorella C.

review about Discovering the island of Kefalonia and Zakynthos in total relaxation - hostess on board August 2019

10 / 10
Wonderful holiday! Roberto, experienced skipper, as well as excellent host, always attentive and helpful, gave us fantastic moments. Together with him and the wonderful Romina we spent beautiful days, discovering spectacular places: beautiful sea, beautiful coves .... in short, everything superlative! Experience to be repeated as soon as possible!!!!
Daniele R.

Daniele R.

review about 7 islands in 7 days sailing between the Ionian islands August 2019

10 / 10
Massimo is a great skipper. Prepared and attentive, it instills safety in the crew members in every situation and condition of navigation. A great connoisseur of the sea, he has as his strong point a deep and sincere passion for what he does. passion that inevitably transfers to the crew members making sure that the holiday goes far beyond navigation. With Massimo you can appreciate the wonders of the sailboat lulled by the waves and pushed by the wind. When it comes to eating and having fun, Massimo is able to meet everyone's needs by offering typical cuisine on board, aperitifs at sunset, dinners in typical restaurants or more mundane evenings. Thank you very much Massimo, I hope we will sail together again.
Marco P.

Marco P.

review about The history of Rhodes, the charm of Chalchi, the life of Simi, the silence of Alimia, Max 4 guests August 2019

10 / 10
Wonderful holiday. The boat is a gem always tidy and clean. Warm and welcoming atmosphere. Giorgio and Viviana impeccable with their immense experience of navigation and knowledge of the Greek islands. Comfortable and relaxing holiday, but at the same time exciting, sailing through these wonderful islands. Perfect itinerary: right mix of unmissable places between pristine bays and coves and isolated marinas. Maximum care and attention to guests for any need or request for navigation, participation in maneuvers, food or other .. Viviana's cuisine is surprising: quality products and it is incredible what she can prepare on the boat. Hospitality, friendliness and hospitality truly unique. Giorgio and Viviana have amused and enchanted with their experiences of travel and navigation in remote places in the world. Perfect formula with few guests on board that allows rhythms and really comfortable spaces. Unforgettable experience. I would start again immediately!
Patrick P.

Patrick P.

review about ALL INCLUSIVE crewed sailing holidays between Nafplion & Poros, both near Athens July 2019

10 / 10
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
Gloria B.

Gloria B.

review about Sailing in the North Cyclades from Lavrio (Athens) September 2018

10 / 10
Unforgettable trip, great places. Lorenzo a very good skipper, always knows what to do in any situation, knows how to make an unexpected a good opportunity, exceptional cook!
Giangiacomo R.

Giangiacomo R.

review about Paros, Milos or the Little Cyclades on a wonderful and new Lucia 40Catamaran July 2018

10 / 10
A wonderful holiday in good company among the Cyclades islands, always accompanied by a sustained Meltemi, but quiet for the safe and prompt governance of the boat by Daniele and his partner Ellina. Thank you, see you soon! :)
Lina C.

Lina C.

review about Catamaran Cruise in Cyclades with Hostess from Athens to Milos August 2018

10 / 10
Christian was very nice... the assistant always kind and helpful! Large spaces in the cabins of the catamaran, comfortable holiday, despite the rough sea in Greece!!! The group very pleasant! It was fun everything, in short! I recommend it!!!
Mariella M.

Mariella M.

review about Offshore sailing on a Swan 65 from Sicily to Patras July 2018

10 / 10
This flight from Syracuse to Kefalonia in just 36 hours is unforgettable! Unforgettable the starry skies of the Mediterranean, the milky way and the moon contemplated in this offshore navigation on the oldest route to Greece. Pieter, own and skipper, proved to be skilled, experienced and as his friend Rob tireless sailors. Pieter has shown surprising resource in managing this navigation that in some moments has turned in a real adventure. And despite the effort required by the shifts of uninterrupted navigation, in my night of seakness, Pieter has found away to nurture me carefully. The boat proved to be an unsurpassable vessel! Enjoy!
Filipa C.

Filipa C.

review about Relax in the comfort of a classic Hallberg-Rassy 49 with skipper and hostess June 2018

10 / 10
We’ve had an amazing week aboard! Super relaxing experience, Pierre and Marion were 100% available and took us to the most amazing spots across the Cycliades. They made sure we were happy all the time and provided for a remarkable week!! HIGHLY RECOMMEND!
Maddalena P.

Maddalena P.

review about This summer I invite you on board for a holiday "Sailing, Fitness, Good Food and Spa" June 2018

10 / 10
Beautiful week between the bays of Corfu, Paxos and Antipaxos, with a couple of stops on the mainland. Manuele is very attentive, patient and available to explain the notions of sailing, as well as involving the crew in all maneuvers. We ate very well, with little he manages to prepare an exquisite lunch. An experience I recommend!!! Thanks Manuele :)
SIDONIE L.

SIDONIE L.

review about Luxury cruise in the small Cyclades with skipper and hostess, All inclusive May 2018

10 / 10
We had the chance to spend a week with Jérôme and Depy for a first cruise in the Cyclades. Our stay was wonderful in every way, a great boat, beautiful scenery, but above all an unforgettable welcome. Jérôme and Depy took the time to make us discover their universe, to explain the principles of sailing, to share with us authentic dishes, to take us to intimate and splendid corners, also to listen to our desires, etc. Between them they conquered us and gave the desire to start the adventure again very quickly! A huge thank you!!! "Good Wind" :) David & Sidonie
Giorgio M.

Giorgio M.

review about ABSOLUTE LUXURY - Two-week flotilla in the Cyclades August 2017

10 / 10
An exciting, dynamic and fun experience. Perhaps, even considering the sea/wind conditions, it would have been better to reduce the stages with longer stops... However, I hope to have the opportunity to repeat this beautiful adventure. Giorgio
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