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Yacht sailing holidays & skippered tours in Dodecanese

Yacht sailing holidays & skippered tours in Dodecanese

Discover hundreds of sailing holidays in the Dodecanese Islands. Book a spot onboard and live a unique experience with a local skipper. Starting at €400 a week.

  • Sailing Holidays
  • Greece
  • Dodecanese

FLEXIBLE CANCELLATION.

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

  • 32 reviews
    almost
    confirmed

    Kufner 54, the alternative to the Catamaran - boarding in Rhodes

    from 5 May - 7 nights
    Dodecanese Greece
    Join in on this experience!
    769€ Per person
  • 32 reviews
    almost
    confirmed

    Kufner 54, the alternative to the Catamaran - boarding in Rhodes

    from 13 May - 7 nights
    Dodecanese Greece
    Join in on this experience!
    769€ Per person
  • 7 reviews
    confirmed

    Sailing for the Dodecanese: from Rhodes to Rhodes to discover Karpathos

    from 18 May - 10 nights
    Dodecanese Greece
    3 people
    are onboard
    689€ Per person
  • 32 reviews
    almost
    confirmed

    Kufner 54, the alternative to the Catamaran - boarding in Rhodes

    from 20 May - 7 nights
    Dodecanese Greece
    Join in on this experience!
    769€ Per person
  • 7 reviews
    confirmed

    Sailing for the Dodecanese: from Rhodes to Kos

    from 28 May - 7 nights
    Dodecanese Greece
    6 people
    are onboard
    636€ Per person
  • 29 reviews
    confirmed

    From the Dodecanese to the Cyclades, from Kos to Milos in 10 days

    from 14 June - 10 nights
    Dodecanese Greece
    1 person interested
    in this holiday
    696€ Per person
  • confirmed
    whole boat only

    On a catamaran in authentic Greece away from mass tourism

    from 29 July - 7 nights
    Dodecanese Greece
    Reserve this boat!
    (7 spots available)
    930€ Per person
  • 34 reviews
    almost
    confirmed

    Cabin boarding, From the Dodecanese to Turkey, away from the crowds - Hostess / Chef on board

    from 29 July - 7 nights
    Dodecanese Greece
    1 person
    is on board
    1.378 1.325€ Per person
  • 32 reviews
    almost
    confirmed

    Kufner 54, the alternative to the Catamaran - ALL INCLUSIVE

    from 30 July - 7 nights
    Dodecanese Greece
    Join in on this experience!
    1.590€ Per person
  • 34 reviews
    almost
    confirmed

    Sailing cruise on luxury 17m.boat from KOS to the Dodecanese NORTH - Chef on board / hostess

    from 5 August - 7 nights
    Dodecanese Greece
    4 people interested
    in this holiday
    1.590 1.537€ Per person
  • 32 reviews
    almost
    confirmed

    Kufner 54, the alternative to the Catamaran - ALL INCLUSIVE

    from 6 August - 7 nights
    Dodecanese Greece
    1 person interested
    in this holiday
    1.590€ Per person
  • 34 reviews
    almost
    confirmed

    LUXURY SAILING HOLIDAY, From KOS, South Dodecanese and Turkey with CHEF

    from 12 August - 7 nights
    Dodecanese Greece
    Join in on this experience!
    1.908 1.855€ Per person
  • 1
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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 Dodecanese

139 reviews
18 / 10
Carlo S.

Carlo S.

review about Patmos, Lipsi and Leros on a luxury fast Catamaran, year 2021 with private bathroom August 2022

10 / 10
We harnessed ourselves on August 6th in Samos and disembarked on the 21st in Leros. Spectacular holiday . Katapliktiko! Exceptional professionalism of the skippers Daniele and Elline, in all the roles they have covered. Great technical preparation and maximum commitment to the choice of the most beautiful and significant places ... nothing left to chance , even with alternative options! Every day new places, carefully selected. Challenging sailing without reservations, special people for a special and unforgettable holiday, very technical fast cat, with spacious cabins. Thanks Daniele and Elline 10 laude
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!
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.
Leo L.

Leo L.

review about Dodecanese Greece on a sailing boat (skipper + staff on board and galley service) July 2022

10 / 10
I can only thank Pierluigi and Nicoletta for the unforgettable experience they made me live in this incredible week. Always smiling, attentive to needs, kind to all participants. Experts both in logistics, making you find the galley already organized, and in programming, constantly monitoring weather conditions and always knowing how to propose engaging alternatives. Given my interest, although totally inexperienced in sailing, they involved me in the maneuvers, patiently explaining how to move and behave in the phases of both navigation and mooring. I observed the special attention paid to the guests as well as the great patience, which comes from the deep passion and love they have for the sea and sailing. I knew it would be a wonderful experience but I couldn't have imagined how much it would remain in my heart. Mine is just a goodbye to these incredible sailors. Strazzabosco
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.
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 :) :) :)
Vincenzo M.

Vincenzo M.

review about Discovering the Dodecanese in total relaxation with hostess on board! August 2021

10 / 10
Unfortunately the program does not allow you to give more than 5 stars, because they would be well deserved! A top week, among wonderful islets, scary backdrops and lots of sea life and sailing! Roberto and Romina have been living on the boat for years, and they welcomed us into their home as very welcome guests! Their professionalism, hospitality and friendliness accompanied us throughout the trip, also Romina is a great cook and Roberto (Capitan Rupi) makes scary cocktails! Being our honeymoon they were also so nice that we found a very welcome gift. We recommend everyone to take advantage of this magnificent week if you are looking for relaxation, sea life and good company!
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.
Ian T.

Ian T.

review about A tasty holiday, the Dodecanese islands September 2019

10 / 10
Unforgettable, amazing experience. One of those events in life that will be talked about for many years to come. Emanuel exceeded our expectations in every way possible and he does it so effortlessly. He is an extremely competent Skipper and even though we had some rough weather whilst sailing... at times winds up to 40 knots, he was always calm and totally understood the situation at hand. He made us feel relaxed at all times. He is an accomplished chef... and I say chef... not cook, the meals he prepared were fabulous. Nothing was too much trouble for him and he always asked if things were ok for us. He is thoughtful, respectful, helpful to all, not only us on the boat, he was constantly helping other boats when they had troubles. He knows all of the secret spots in the Dodecanese which gave us some secluded undisturbed evenings away from others and protected from overnight winds. Emanuels boat is very well equipped for ALL situations .. and I have run out of lines to writ any mor
ELVIRA E.

ELVIRA E.

review about A sailing cruise in the big blue of the Dodecanese July 2019

10 / 10
Wonderful holiday for me and my children (who received the "baptism" of the sea!) to be repeated as soon as possible!! Luigi and his daughter Veronica welcomed us with loving care and impeccable professionalism! Beautiful itinerary, amazing sea, sail in relaxation and much more!
Fabio F.

Fabio F.

review about Flotilla 10-24 August Dodecanese August 2019

10 / 10
Andrea was very kind and professional already at the stage of describing the holiday weeks before leaving, helping me to understand what my first sailing holiday would have been like. Throughout the holiday he even explained to me many notions about sailing and navigation. Definitely a very good skipper. I recommend it!
Eleonora P.

Eleonora P.

review about "Sapori in Bolina" in Dodecanese - ALL INCLUSIVE in Flottiglia - LAST MINUTE DISCOUNT! August 2019

10 / 10
Claudio is a competent and reliable skipper. He also turned out to be a really nice, welcoming and positive person! My holiday went very well and therefore I recommend everyone a holiday with him (and Carmen)! Thanks for everything Claudio! See you soon!
Adalberto G.

Adalberto G.

review about The perfect Mini Flotilla among the wonders of the Dodecanese - In flotilla with Daniele T. - LAST MINUTE OFFER August 2019

10 / 10
I found myself very well with Luca, good people, good skipper and he knew how to better manage difficult situations. I hope to get back on the boat with him . Good ???? wind
Andrea Antonio T.

Andrea Antonio T.

review about Dodecanese 2 - The northern islands - In flotilla with Luca N. August 2019

8 / 10
Daniele is an excellent and prepared skipper. He is also an extremely friendly and engaging person, and knows how to create the right atmosphere on board. It also involves you in maneuvers and does not skimp on explanations. What can I say, absolutely recommended!!
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!
Virginia D.

Virginia D.

review about Sailing on the discovery of the Dodecanese April 2019

10 / 10
Wonderful holiday!!!! Emmanuel is a skipper very experienced in leading his beautiful boat, extremely prepared on the places visited, very caring towards his guests as well as a person of culture with whom it is very pleasant to converse. Not to mention the stages he chose that really leave you breathless. We don't know how to thank for this experience!
Marco G.

Marco G.

review about Sailing around Kos August 2018

10 / 10
Luca is a great skipper. A helpful, smart, fun person to spend a week on the boat with (and a great fork). The holiday is spent in great relaxation. He will pass on the passion for the Aegean Sea that he knows very well. If you want to participate in the maneuvers and / or go for a jog at dawn to dispose of one of the many dinners in the tavern there will be no problem! highly recommended
Marco Paolo R.

Marco Paolo R.

review about Luxury sailing on Swan 65 exploring the Dodecanese August 2018

10 / 10
Pieter is a great skipper and the boat is pretty amazing! You can learn a lot from him about sailing and organization .
Savino D.

Savino D.

review about The best of the Dodecanese on a magnificent Sun Odyssey 49 August 2018

10 / 10
Perfect holiday and navigation with Fabio in the Dodecanese! I appreciated first of all that Fabio keeps the boat tidy, clean and very well organized, and that it welcomes a small number of guests compared to the size, in order to enjoy privacy and adequate spaces. I also really liked the times, with the right mix of navigation and relaxation for baths and dinners. Fabio is a great connoisseur of the Greek islands, so the places he chooses are always the best, and sometimes even out of the loop that other boats normally do. Finally, I would also like to stress the patience with which he explains the technical and navigation aspects; excellent opportunity for some guests who want to refresh or improve their skills. Super-recommended!
Chiara A.

Chiara A.

review about Fun and relaxation on a beautiful sailing boat in Greece Dodecanese July 2018

10 / 10
Very competent, he fulfilled our wishes to visit some islands of the Dodecanese even though the wind was not always on our side. Rather shy but very friendly, he always made us feel comfortable and cooked us good lunches. Also his boat is very well maintained and comfortable. Experience definitely to recommend! Merci milles fois capitain!
Philippe V.

Philippe V.

review about Kos - Kalimnos - Lipsi - Patmos - Leros. Dream week between sailing, sea and (if desired) free c June 2018

8 / 10
We spent a fantastic week with Riccardo who knows his boat very well, finds wonderful spots to spend the night at anchor or clinging to a buoy. Riccardo allowed us to do a lot of maneuvers which completes our nautical training. Security is on the agenda.
Lisa O.

Lisa O.

review about Dodecanese pearls: Kalymnos, Leros, Lipsi, Arki and Patmos - flights to Kos September 2017

10 / 10
I had a wonderful time on Massimo's boat. It was a good mix between chilling and activities, we had perfect weather, good food, we visited great places and we were always in good mood.. what's more?! Massimo ist really a "sea expert" and with him I had the chance to learn a bit more about sailing and about the sea. I recommend this holiday!!
Giuseppe L.

Giuseppe L.

review about NORTH DODECANESE from KOS:Kalimnos,Patmos,Lipsi,Arki on a luxury boat with skipper and hostess/chef July 2017

10 / 10
Sailing with Renato and Luciana was a great experience. The Queen II is a superb boat for a superior category holiday, but ready to bring out the 'sporty' soul when the wind makes itself felt. The skipper does not miss an opportunity to raise the sails and test the guests at the helm. We visited very nice places, away from the confusion. A special mention for Luciana, always smiling, from the musical good morning (what an atmosphere her breakfasts!) to the evening chat. Not forgetting the delicious lunches in the cockpit! And we will never stop thanking her for the celebration on board Bianca :) Renato is an experienced skipper, a safety at sea. But also a beautiful person, who has shown flexibility in modifying the itinerary to meet the needs of his guests. A very nice holiday also for the harmony that was immediately created with the other two couples on board. To Renato and Luciana we say: see you soon! Giuseppe and Bianca
Matteo P.

Matteo P.

review about Wandering in the Dodecanese Archipelago August 2017

10 / 10
Excellent skipper, very prepared and competent and passionate about boats and sea. Well organized holiday with a super crew. Absolutely recommended!!
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