14 Night/13 Day Itinerary Sail Around the Greek Islands of the Cyclades

Saturday: After getting settled in on the boat, having a refreshing aperitif and getting acquainted with the captain, you will be our guest when we take the tram from Alimos marina and if you like, we’ll direct you to one of the best places to shop for unique items, and then dinner is on us at an authentic taverna in the Plaka quarter.

Sunday: We start on the island of Kea, once a haven for pirates. Kea is rich in olive trees, almond trees and old, strong oaks, whose acorn shells were once used to make dyes, and boasts ancient temples, ruins and plenty of beautiful, uncrowded beaches for your pleasure. Carnival (or Apokreas) is celebrated in the time before Lent. Must see: Giant stone lion who smiles as he looks down on the hills he has guarded since before the days of Socrates...

Monday/Tuesday: Next we sail to Mykonos for 2 days of glitz and glamour, which is why so many celebrities own second homes and spend their vacations here. The south side of Mykonos offers miles of white sandy beaches (including nude and gay beaches) and is a mecca for shopping and fine international dining, and you can dance till dawn in your choice of clubs.
Mykonos also offers some of the most spectacular diving spots in the Med.

Must see: The Aegean Maritime Museum and the Archaeological Museum (which has on permanent exhibit a 7th-century BC storage jar, decorated with scenes of the Trojan war, and a trip to the neighboring island of Delos, to the archaeological site (covered in white marble) which rivals Olympia and Delphi on the mainland.

Wednesday: Our next stop is the island of Ios - a literal Fountain of Youth in the Cyclades. At first glance, IOS seems like many other Greek Islands - white houses climbing up the olive green hills, long sandy beaches and authentic tavernas in the capital city of Chora. But when the sun goes down, the city comes to life as doors open, music blasts out and the parties last till dawn… Enjoy the international cuisine and every type of water sport.

Don’t miss: The tomb of the poet Homer (whose mother was born on Ios).

Thursday/Friday/Saturday/Sunday: For the next few days we’ll be anchored off the island of Santorini, one of Greece’s most famous and beautiful islands. (Where else can you enjoy a cool drink suspended over the rim of an active, sea-filled volcano?) Santorini is also famous for it’s blacksand beaches, spectacular sunsets and a virtual shopper’s paradise. Famous also for its wine, you’ll enjoy a trip to the Sigalas vineyards for dinner and a wine tasting. The winery is located on the plain of Oia called Baxedes, and grows Assyrtiko, Athiri, Aedani, Mandilaria and Mavrotragano grapes. On the far side of Santorini is the village of Akrotiri and the famous Minon ruins. You should also visit the terraced ruins of the ancient city of Thira, which look out over the sea and date back to the 3rd century BC. Artifacts from the Ptolemies, Hellenistic and Roman civilizations have all been unearthed here. Nights on Santorini are lively and varied, with something to match every tastes - you’ll also find traditional Greek music here.

Monday: Our next journey takes us to the unspoiled island of Folegandros - a place Conde Naste once called “Greece’s most beautiful undiscovered island”… On the south side are steep cliffs. The village of Hora is one of the oldest medieval villages, and motor vehicles are not allowed inside. The buildings, which are very close to each other, form the outer castle wall. Keravostassis is a small seaside village where you’ll find colorful wooden fishing boats, whitewashed houses and a pebble beach.

Must see: The center square of Hora, which is really three squares set one after the other, lined with trees and ringed by authentic tavernas.

Tuesday: Today we travel to the fourth island of the Cyclades called Sifnos, which has been inhabited since 3000 BC (the early Cyclades Period). This island has a little of everything - beautiful mountains, lush valleys, golden sandy beaches and fascinating little villages with white-washed buildings. Snorkeling is excellent here, the bays are sheltered and the water is crystal clear and warm. Sifnos is known for its fine cuisine, and some of the finest chefs in all of Greece are found here. There are also ancient ruins, monasteries and 365 churches on this island.

Wednesday: Then it’s on to Syros which is a living museum waiting to be explored. The city of Hermoupolis (named after the Greek God Hermes - the God of commerce) is the capital of the Cyclades islands and is an authentic 19th century city that offers Neoclassical buildings, rock walls that have been battered by the waves for centuries, and a fascinating section of the city known as Vaporia (the ‘Sea Captain’s quarter’), where you’ll discover elegant white mansions that seem to rise up out of the sea.

Don’t miss: eating freshly grilled octopus with a drink of Ouzo in an authentic Greek taverna.

Thursday: Our next port of call is Kythnos, a volcanic island that is both barren and rugged and offers more than 70 beaches - many of which are inaccessible except by boat… Chora is the capital and it’s worth a visit to see this medieval village and its Church of the Trinity. Must See: The Village of Loutra (which is about 4.5 km from the capital city of Chora), famous for its hot springs where people have come to bathe in the healing waters and be cured of what ailed them for centuries.

Friday: And finally, we sail to Cape Sounion and the breathtaking Temple of Poseidon, one of the most visited and photographed ancient wonders in Greece… The temple, which sits 60 meters above the headland and surrounded by water on three sides. The temple was dedicated to the Greek God Poseidon. A little further down you can discover the ruins of another ancient temple, this one dedicated to the Goddess Athena. It’s not an exaggeration to say that some of the most beautiful sunsets in the world are seen here.

Saturday: The journey ends here, as we’re back in port. Your driver will take you to a hotel or the airport. We wish you a safe journey home.

A little information about the Cyclades Islands:

The Cyclades islands are the central group of islands in the Aegean Sea, and there are 21 large islands and 20 small islands, all forming a kind of ring around the rocky island of Delos (the word ‘cycle’ means ring in Greek).

In addition to being some of the most beautiful and most-visited islands in Greece, the Cyclades have a rich and fascinating historical significance as well, dating back to the times of antiquity. Thanks to archaeological excavations we know that several of the islands have been inhabited since the early Cycladic period, and the ruins, relics and riches left behind are the source of endless speculation and discussion about the lifestyle, culture and art of the people who first lived, loved and worked here.

During your cruise with Seapaths, (especially if you choose the 14 night cruise) you will have the opportunity to explore the art, culture and living history of ancient Cyclades that few others ever get to… You’ll also enjoy the beautiful beaches (the black sand beaches at Santorini are extraordinary), the white-washed houses and mansions, typical windmills, small taverns featuring delicious authentic Greek food and wines, the narrow stepped streets, museums, water sports, and fabulous shopping.