31 Oct 2023
2 week cyclades


Those who have decided they need a well deserved vacation in absolutely breathtaking locations as well as rich cultural and historical sights to explore, are in for a real treat if they have their minds set on the Greek Islands. More often than not, the destinations they will have their hearts set on are somewhere in the Cyclades Islands complex. These islands are famous around the globe for their stunning beaches, incredible hospitality, rich history and culture, and last but not least their very distinct and beautiful white washed architecture with charming town squares and villages. The most famous of these islands are probably Mykonos and Santorini, however there is so much more to this region than first meets the eye.  

There are around 27 islands located in the Cyclades region, comprising 20 larger islands and 7 smaller ones. They all have their fair share of resemblances, however each possess a unique atmosphere and characteristics upon arriving and exploring them. All are blessed with gorgeous landscapes and each island has its own beautiful beaches and swimming areas. Some islands have more greenery while others are rustic and dry but still retain their own incredible untamed beauty. When visiting the Cyclades region it will be quite easy when it comes to island hopping seeing as most of them are in close distances to each other. 

Exploring the Cyclades islands from Athens aboard a yacht is a fantastic way to experience the beauty and culture of this Greek island group, and also one of the most efficient means to get the most out of a Greek Island vacation. A two week sailing itinerary in the Cyclades can provide you with a fantastic opportunity to explore the beauty of the Greek islands from the sea. 

Here's a suggested itinerary for a great sailing adventure:


Day 1: Athens to Kea

Start your journey in Athens.

Sail to the nearby island of Kea (Tzia), known for its charming villages and beautiful beaches.

Explore Vourkari and Otzias.



Also read: Luxury Vacation in Athens



Day 2-3: Kythnos

Sail to Kythnos, a less crowded island with picturesque coves and thermal springs.

Anchor at Kolona Beach and enjoy the unique double beach.

Explore the main town of Chora and Loutra for the thermal baths.


Day 4-5: Serifos

Set sail for Serifos, an island with a rugged landscape and lovely beaches.

Visit Livadi, the main port, and hike up to Chora.

Explore the beautiful Psili Ammos and Vagia Beaches.


Day 6-7: Sifnos

Sail to Sifnos, known for its traditional architecture and culinary delights.

Explore Apollonia, the island's capital.

Enjoy the picturesque beach of Kamares and the scenic village of Artemonas.


Day 8-9: Milos

Head to Milos, a unique island with striking geological formations.

Visit the famous Sarakiniko Beach and the catacombs.

Explore Plaka, the island's capital, and relax on Paleochori Beach.


Day 10-11: Kimolos

Sail to the nearby island of Kimolos, which is often overlooked by tourists.

Explore the charming Chora and enjoy the tranquility of Prassa and Bonatsa Beaches.


Day 12-14: Santorini

Sail to Santorini, the most famous Cycladic island, and anchor in the caldera.

Explore the towns of Fira and Oia, and take in the stunning sunsets.

Visit the archaeological site of Akrotiri.

Relax on the unique Red Beach and White Beach.


Day 15: Return to Athens

Sail back to Athens.

This sailing itinerary offers you the opportunity to explore the diverse beauty of the Cyclades, from serene and lesser-visited islands to the iconic Santorini. Adjust the itinerary based on your sailing abilities and preferences, and be sure to check weather conditions and mooring options at each destination. Enjoy your sailing adventure in the Cyclades! A luxury catamaran with a crew included will surely elevate this whole experience, allow your skipper to guide you to some of the most picturesque locations on the planet as well as guide you away from the usual tourist traps many experience during a trip to the islands. Learn all the secret hangouts and must see locations from your trusted crew who will have incredible knowledge and insight of the areas you will be visiting during your sailing vacation. Therefore they will not only guide you safely through the sea, but they will also be your own personal hosts during your stay in this breathtaking country. 


You can also check 1 week cyclades itinerary here!