Sailing Charter Holidays in Greece

Sailing Holidays In The Cyclades

Join us for a unique and unforgettable journey where relaxation and fun prevail

Choose one of our Adventure Packages below or check out our Special Offers


Osyan yacht anchored in a beautiful bay

Discover The Small Cyclades Islands

Enjoy a 7 day trip around the Cyclades islands. Our skipper and Crew will take you to 6 different islands of your choice, like Mykonos, Naxos, Paros, Ios, Santorini, Amorgos.



Sailing in the Aegean sea

Cyclades Family Week

A true holiday! A 7 days amazing experience that you & your kids will never forget. Relax on board, learn to sail, visit sandy remote beaches and much more.



Mykonos Island

Ten Days From Mykonos To Santorini

All Inclusive. Sailing From Mykonos to Santorini. A tour around the Cyclades islands. Starting from Mykonos and finishing at Santorini. Total trip duration: 10 days.



Osyan charter yacht

Discover The Sporades Islands

Discover the beauty and peace of the Sporades Islands in a 2 weeks cruise! Sporades are located in the east coast of Greece and their name means "scattered".


Yacht Osyan Presentation Video



KiteSurfing In The Cyclades

Come or learn kitesurfing with us in the Cyclades, one of the best places in Europe. Flat, calm waters or waves, your choice!



Diving in crystal and clear water

Diving In Crystal Water

One of our favorite activities is diving. Dive in crystal clear water and many interesting dive-spots such as caves, wrecks, etc.



yoga activities


Combine Your Holiday With Yoga. The emphasis of the class is on fluidity through the breath and awareness through the body.


Sailing The Cycladic Islands In Greece

A unique and life changing experience combining seamanship and holistic living, by the hand of our Captain and Crew who will provide the atmosphere for an unforgettable journey wherever we sail.

Our crewed charters consist of 1 or 2 week tours around the Cyclades, visiting islands such as Kithnos, Kea, Serifos, Andros, Tinos, Mykonos, Paros, Naxos, The Small Cyclades Islands, Santorini, and Ios with a choice of many others.


Visiting Different Islands

In one week we can visit around 5 to 6 islands sailing for about 3 hours a day from one island to another.

We can drop anchor in impressive turquoise coves tucked away on the small islands where amazing natural scenes and colors combined with the taste of traditional Greek life unfold.

Sailing in Greece
Passage between islands

Your Skipper

Sotirios Fouroulis has been a qualified skipper for over 20 years sailing not only around the Greek Islands but also in South America.

Whether you want a quiet relaxing break or an action packed fun holiday Sotirios's wealth of experience and knowledge with Cyclades Sailboat Charters and the Greek islands will ensure you have an absolutely fantastic time!

Sotirios Fouroulis
Sotirios Fouroulis


Activities during the week include swimming, snorkeling, hiking, sailing lessons, Thai Chi practice in the mornings, BBQ's on uninhabited islands at night and visiting picturesque towns.

Enjoy traditional Greek cuisine and on some islands have the choice of going to bars or discos.

We will visit some archeological sites on islands such as Delos.


Crewed Charters - With Hostess / Cook

A hostess will be cooking up to 3 meals each day, serving beverages and snacks, sun downers in the evening as well taking care of the house keeping on-board.

We can anchor in idyllic and peaceful bays under the stars at the night.

Along the way you may be lucky enough to see dolphins swimming alongside the boat.

Sailing with dolphins
Sailing with the dolphins

Crewed Charters - Self Catering

There is a full equipped galley available for the passengers to prepare breakfast, lunch & dinner if they so desire.

Each afternoon we can in moor in a marina and in the evening you have the choice to wine and dine at a taverna or restaurant as opposed to preparing your meal on board.

A taverna in Oia, Santorini

The Cyclades Islands

The Cyclades Islands is the group of islands lying in the Central Aegean Sea, it's the most visited and beautiful group of islands in Greece.

These islands are connected to the mainland and many to each other by the Greek ferry companies.

Portara, Temple Of Apollo, Naxos

What our clients say abouts us!

"The greatest holidays ever mama". That's what my kids told me during this trip with Sotiris.


Just beautifull! A wonderfull vacation, a must in lifetime experience! Thank you Sotiris for such a magical voyage!

Tessa & John

Simply Awesome!! What a Country! The sea, the sky, no words to explain it. Thank you Sotiris and Zeo for such an amazing experience, you will have us next year again for sure in this lovely boat.

Rolf , Judith, Franz and Peter