Catamaran yacht sailing holidays & tours in Greece
The Greek isles and their vast amount of coastline - of more than
16,000km is home to some of the world’s most beautiful islands and
beaches. Embark on a beautiful sailing adventure aboard a spacious,
comfortable catamaran.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
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Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
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 - Catamaran yacht sailing holidays & tours in Greece
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.
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 :) :) :)
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!!!
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!
Truly bubbly holiday, with crazy travel companions, upwind sails with more than 20 knots of wind, white beaches, swimming in incredible bays, breathtaking sunsets and evenings of joy and fun
Thanks to the group of tireless skippers who organized our stages perfectly, but even more for our skipper Samuele who proved to be very professional, nice and willing to satisfy our whims.
Definitely see you next time.... Good wind to all
I have taken several boat holidays but a skypper like Luca I have never found. Attentive to everything, respectful of the sea and those who live there. Before being a skypper he is a sailor with a genuine and beautiful spirit. One who loves the sea and transmits it..
Perfectly organized trip with an impeccable team behind them. I would start again immediately!
Highly recommended holiday fantastic experience, Giorgio and Connie are two wonderful people, their experience, hospitality and sympathy have allowed us to live a unique "sailing" that we suggest to everyone. A praise also to the rest of the participants with whom a beautiful friendship was born.
Last but not least, a praise also to the Catamaran for the wide spaces and the environment that you breathe on board ...... and as stated on the first day by Giorgio, if you try it you do not abandon it anymore!!!
See you soon
It was an amazing trip.
Max is an excellent skipper, very Nice and take care with the crew.
I really recommande à sail trip with him.
Thank you for everything
See you
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! :)
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!!!
unique experience! nice catamaran, nice baths in Greek waters, our Francois was a great captain, company and sympathy. It can be replicated in the future if there is an opportunity! ;-)
Beautiful holiday aboard Merlin the Wizard. The boat is very comfortable and spacious, spotless. Silvia and Giuliano are two very experienced and extremely professional skippers, with them you always feel safe. Deep connoisseurs of the navigation area, they take you to the most beautiful and less crowded beaches, as far as possible in July in the Ionian Sea...
If you want and are interested, they enchant you with the stories of their adventures in exotic seas, perhaps in front of a glass of rum or a cold beer (depending on the time), in the large and cozy cockpit. . Silvia is an excellent cook and will cook the menus you prefer. I hope to have another holiday aboard Merlin the Wizard soon...
6 reasons to explore Greece on a catamaran for your next sailing holiday:
Discover some of the world’s most beautiful coves and lagoons in the comfort of a catamaran.
Explore the thousands of Greek islands aboard a catamaran with a weak draft, allowing them to venture into shallower waters than a monohull - meaning you can travel with an unrivalled level of freedom!
Board a spacious catamaran, that allows a most comfortable sailing experience possible - especially when travelling as a family or a larger group!
As a catamaran has less movement at sea than a monohull sailboat, it is perfect for first time sailors, reducing any concerns about sea sickness.
Experience all of the treasures of Greece - including the famous isles of Santorini, Mykonos, and Ios as well as the native sirtaki dance of the street festivals.
Immerse yourself into the beautiful atmosphere and charming architecture of Greece’s coastal regions aboard a catamaran.
The best destinations to visit on your holiday to Greece aboard a catamaran:
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. Corfu, Mykonos, and Santorini are some specific destinations that are particularly magical to explore by a sailing holiday.
Travelling the Greek isles by sailboat allows for full exploration of the areas treasures, that would otherwise be inaccessible. This is even more so the case when travelling by catamaran, due to the weak draft of the boat, meaning shallow waters inaccessible to many monohull boats can be explored! 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. Learn more about sailing in Greece.
Tips to help you to better plan for your next sailing holidays in Greece aboard a catamaran:
When to visit Greece & transport options
Temperatures and the climate in Greece are pleasant and generally good for sailing from April through to November. Due to the fact that July and August are more popular for holidaying, if possible, it is worth considering travelling during May, June, September, or October if you would prefer a quieter, slightly more tranquil holiday.
Greece is home to a number of international airports such as Athens, Corfu, Kos, and Kefalonia. Greece has a well developed system of ferries that transport travellers from island to island. The organising skipper of any given trip will be able to give you the most relevant information about transport routes to and from your points of embarkment and disembarkment.
Sailing with a family aboard a catamaran with a local skipper
There are some sailing regions that are better suited and equipped for family sailing trips, and Greece is one of these regions. There is a good mix of modern marinas and harbouring options as well as more secluded bays and coves for you to enjoy with your family. All forms of sailing holiday with family holidays included, benefit greatly from having an experience local skipper leading the trip. Travelling with a skipper with such insider knowledge allows you to fully immerse yourself in the enjoyment, relaxation, and adventure of the sailing holiday in the Greek isles.
