YachtSailingYachtSailing

Sailing Blog · Itinerary

2 WEEK CYCLADES ITINERARY

By YachtSailing Editorial Team·5 min read·

In short

2 WEEK CYCLADES ITINERARY is a 8-day sailing route through the Greek islands aboard a private catamaran, starting and finishing in Athens to Kea. It takes in 3: Kythnos, 5: Serifos, 7: Sifnos, 9: Milos, 11: Kimolos and 14: Santorini - whitewashed villages, hot springs and some of the Aegean's clearest waters. Departures are mainly on Saturdays, and the route can be tailored to your pace with a private skipper and hostess on board.

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.

2 WEEK CYCLADES ITINERARY
Sailing the Greek islands with YachtSailing
The 8-day route
Day1

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
Day2

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.
Day3

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.
Day4

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.
Day5

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.
Day6

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.
Day7

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.
Day8

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.

Good to know

How many days is the 2 WEEK CYCLADES ITINERARY?

+

It is a 8-day round-trip itinerary, embarking and disembarking in Athens to Kea (typically from Alimos Marina, Athens).

Which islands does this route cover?

+

3: Kythnos, 5: Serifos, 7: Sifnos, 9: Milos, 11: Kimolos, 14: Santorini.

Where does the sailing trip start and finish?

+

The trip starts and ends in Athens to Kea. Most departures take place on Saturdays.

Can the itinerary be customised?

+

Yes. Each island has its own character, so the route can be adapted to your interests, pace and the weather. A private skipper and hostess sail with you throughout.

Explore the destinations
Cyclades
Cyclades
Mykonos
Mykonos
Santorini
Santorini
Related articles
LITTLE CYCLADES ITINERARY

LITTLE CYCLADES ITINERARY

1 week Cyclades Itinerary

1 week Cyclades Itinerary

Healthy Activities Sailing The Cyclades

Healthy Activities Sailing The Cyclades

Ready to sail this route?

Tell us your dates and crew size and we'll tailor a private catamaran itinerary across the Cyclades - skipper, hostess and all.

Ask an advisor

Get in touch

Contact usSend an enquiry, a real advisor replies personally Arrange a video callPick a time that works for you Call us+30 693 723 4566 WhatsApp usAlso available on the same number