Welcome to SailTheGreekIslands.com

Fabulous Experience!
We absolutely loved our sailing adventure with Yiannis.


Dear friend Greetings!

We are a Canadian Yacht Charter Agency specializing in Skippered Yacht Charters in the Greek Islands.


  Sailing the Greek Islands is one of the Most Unbelievably Beautiful, Interesting and Wonder-filled Holidays YOU could ever imagine!


The Companies we represent are the most reputable and long-standing Yacht Charter Companies in Greece…


You will get immense value on your skippered yacht charter in the Greek Islands by booking your trip with us because;


1) We can find you the best quality yacht at the lowest price and at the most suitable location!

2) We have a fluently bilingual in English and Greek, Greek Canadian, friendly and experienced Skipper, who knows the waters, the islands, the best spots to see and swim in, and the historic sites... extremely well… You will be grateful to have Yiannis go along and skipper the yacht and guide you.

3) You are wise to be searching so far in advance, as at this time of year we have good availability of Yachts and Skippers plus we have an early booking discount of 15 % available.

4) You may also choose to hire the services of a Hostess; The Hostess prepares healthy meals with local produce, serves drinks and snacks, keeps the Yacht organized and assists the Skipper with Sailing the Yacht.


Please send us your inquiry with your yacht charter requirements NOW!

Inform us in your inquiry of the following;

1) Time of Year you are able to come... (Our charters normally go on a weekly basis from Saturday to Saturday)

2) Number of persons in your group, or cabins required...

3) If you know, the area you wish to sail in...

4) And whether you need a skipper and/or a hostess....


 We will respond quickly with all the details.


You cannot go wrong with one of our Yachts and our unmatched skipper and Hostess service….


*** Trust SailTheGreekIslands.com  for your Sailing Holiday to the Greek Islands... and rest assured that... you will sail in one of the most reliable and well maintained Top-Of-The-Line Yachts available in Greece…

You will get;

The finest Skipper and Hostess Service!

Up to-date Information!

Expert guidance and understanding…


Don’t settle for second best, rely on the professionals at;  www.SailTheGreekIslands.com


 We Guarantee 100% your satisfaction, your safety and your financial security…


You will Love Sailing the Greek Islands with us!


Best wishes to you and your family!


Tel. ++30 210 964 4792

Cell; ++30 693 235 7340

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Please read the true testimonials from our clients on our guest book in order to understand why you should book your Skippered and Crewed Yacht Charter in the Greek islands with SailTheGreekIslands.com!


We consider the environment always!


Kathy & Charles Thursday, 13 October 2016 01:02  

Sailing with the family!

Our family just returned from a two week sailing trip with Yiannis Stassis. This is the 5th time my husband and I have chartered a sailing trip in Greece and every time it has been a new adventure! Yiannis is a very calm, experienced skipper and we had total faith in his ability to navigate through any situation. His knowledge of the islands and his ability to speak both English and Greek well makes it very easy to maneuver through anything that comes your way. We have had rough water, calm water and everything in between. This is a terrific way to see Greece. We spent time in the more popular spots such as Mykonos and Hydra as well as some very small, charming islands like Iraklia and Ios which were some of our favorites. Sailing allows you to go where many people have yet to travel. The Greek people were always welcoming and helpful to us. The water is beyond beautiful - clear and azure blue. One of our favorite swimming spots was in a bay at Poly Agos which will remain etched in my memory for sure. We saw amazing ruins on Delos where you can try to imagine how people lived over two thousand years ago. So many experiences!! It was a great way to celebrate our 60th birthday with our two (adult) daughters. We had a blast and would recommend it to anyone with a taste for adventure and a love for water.

We are what we repeatedly do; excellence, then, is not an act but a habit.” -Aristotle.

Contact Us

2, Rains Avenue
Toronto, Ontario, M6G 3H5, Canada
14, Skiathou Street
Glyfada, Attiki, 16561, Greece
++ 30-210-964-4792
++ 30-693-235-7340
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