Save Up To 15% On All Yacht Charters For 2020

Sail The Greek Islands... The Best way!

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We had a fabulous sailing experience that, along with the shear beauty of the various islands, was made possible by our Captain. Add in his great knowledge of Greek history and his sense of humour, you have your man. Trust us, you will not be disappointed with your decision to hire Captain Yani. Thanks!

George & Bernadette McCarter

5/5

June 20th 2019

Save Up To 15% On All Yacht Charters For 2020

Get In Touch Today And Secure The Best Offer!

Committed To Sailing Excellence

A five star Greek Island sailing adventure with an experienced and trusted Greek Canadian company for the best trip of your lifetime!

Enjoy the best holiday in memory with SailTheGreekIslands.com.

Crystal clear blue Greek waters. Sun and sand you have to see to believe. People, food and culture that lift your spirits and senses. Dolphins, turtles and whatever other marine life luck brings your way.

SailTheGreekIslands.com provides a safe, comfortable, and relaxed environment, on board top of the line yachts, from which to enjoy it all. Our head skipper, Yiannis Stassis, will choose the ideal yacht for your requirements.

With access to hundreds of yachts and catamarans, available on more than 10 sailing bases for the Greek Islands, he chooses exclusively from yacht charter companies and yacht owners that are known and fully trusted. We ensure the potential pitfalls of chartering yachts overseas are avoided.

See Our 2020 Season Price List

BOOK EARLY FOR 2020 AND GET THE BENEFITS OF THE BEST AVAILABILITY

Our Services

SailTheGreekislands.com is easily the best company to help you feel safe and happy while sailing the Greek Islands on board a good, clean and reliable yacht. We can provide an excellent and knowledgeable skipper to guide your voyage,  or we can help you choose and book the best yacht to skipper on your own.

Skippered Yacht Charters

Our skippers are bilingual in English and Greek, and know the waters, the islands and the best spots to sail-swim-explore very well.

Crewed Yacht Charters ​

We represent fully crewed yachts. Mono-hauls, catamarans and power yachts. Get in touch for all the details.

Bare-boat Yacht Charters

We have a wide selection of bare-boat yachts and catamarans to choose from. Please let us know your requirements and we will reply with suitable offers.

Skippered Sailing Holidays Greece - Sailing The Greek Islands

Skippered Sailing Holidays In Greece

Skippered sailing holidays in Greece at it’s best! You can FULLY TRUST SailTheGreekIslands.com for your sailing adventure around the Greek Islands!


Sailing the Greek islands has never been easier from choosing the ideal Yacht or Catamaran for your requirements, while travelling safely, comfortable and relaxed aboard our Top of the line well-maintained Yachts along with your own personal experienced and knowledgeable Skipper! Get ready for a full 5 stars adventure!


You will ENJOY the best holiday of your life-time and get a Yacht or Catamaran at the location most suited to your needs and at the best price possible, because we get a volume discount and we pass it on to you.

YOU TRUST the experts at SailTheGreekIslands.com and you will be happily enjoying every moment on board from the moment you arrive!

  • Guaranteed 100%.
  • Book early for 2020 and you will get all the benefits!
  • Your number one choice for Skippered Yacht Charters around the Greek Islands!
  • Personalized Canadian quality service.
  • You will connect with your skipper first and then your knowledgeable skipper will assist you in locating the perfect yacht for your requirements.
  • Wide choice of quality Yachts on 10 Bases for the Greek Islands.
  • Over 300 Top of the line Mono-hulls and Catamarans.
  • Full coverage damage insurance/No Deposits (available on our special fleet yachts).
  • Easy booking and payments.
  • Well-Equipped and maintained fleet.
  • Fully trained and experienced skippers!

Happy Stories

We specialize in Skippered Yacht Charters because we are the actual skippers, we know the islands very well and we have a system in place that makes all of our clients feel joyful and content, and nothing makes us feel better than to have our clients super happy throughout their sailing holiday… Please be so kind and read what our clients have to say about their sailing holiday experience with us on our guest-book.

Sailing The Greek Islands - Skippered Sailing Holidays Greece

Well, what can we say!!!!! From start to finish we had the most Spectacular vacation of a life time.

Our Captain Yannis gave us every thing we asked and more. He is the most Amazing Jewel of the Greek Islands. He took the time to listen to our needs and what we wanted. He also educated us on all of the Greek Traditions and Mythology.

Where the locals went for the most traditional food and drink. Lastly, Yannis is a very honest and humble. Even though we have never met his family, we feel like we have known them our whole lives. That speaks volumes. You will not be dissappointed.!!!!!!!

Leigh Ann & Johnny Dyal

5/5

May 17th 2019

Sailing The Greek Islands - Skippered Sailing Holidays Greece

We’ve just spent a week sailing the Greek islands with Captain Yiannis. If your looking for a safe pair of hands, experience and unlimited knowledge of the Greek islands then Yiannis is the captain you need. 

Jeff Brown

5/5

May 10th 2019

May 10th 2019

Sailing The Greek Islands - Skippered Sailing Holidays Greece

We have seen many islands thanks to Yannis, who has an unsurpassed knowledge of the and we might add amazing docking skills! Matoula has been an amazing hostess,a wonderful cook and always gracious with a beautiful attitude. We will never forget our Great Adventure!

Danny and Karen

5/5

June 7th 2019

June 7th 2019

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