Cycladic Islands Charter Itineraries

Rugged and sun-scorched, with iconic whitewashed cubic buildings and golden sand beaches, the Cyclades are Greece’s most popular and glamorous sailing destination. The Cycladic islands charter itineraries usually begin from Athens’ Kalamaki marina on the mainland, though island departures can be arranged.

Your route might take in any of the 33 inhabited islands, such as:

There are also dozens of smaller islets centering on tiny uninhabited Delos. The ancients considered Delos to be sacred.

If sailing the Cyclades in July or August, when the gusty Meltemi wind can reach 7-8 Beaufort, keep your itinerary flexible, depending on sailing conditions.

Most people want to visit Mykonos with its late-night beach clubs hosting international DJs. Also, Santorini, both famous and remote, boasts a dramatic caldera (sea-filled volcanic crater), romantic sunsets, and gourmet restaurants.

Also much-loved by yachters is the wild and rocky Serifos with its 15th-century Venetian fortress, hiking paths, and bohemian vibe, along with Sifnos, known for its authentic rustic cuisine and family potteries making ceramic kitchenware. You can also explore Milos, the island of love featuring extraordinary sea caves, by kayak. Moreover, don’t forget blissful Amorgos, a film set in the 1980s cult movie The Big Blue.

Last but not least, visit Naxos, with its fertile interior, delicious cheeses, sandy beaches, and excellent windsurfing.

Southeast of Naxos, the Lesser Cyclades offer a blissfully peaceful back-to-nature escape. Undoubtedly – our favorite hideaway is Koufonissia, two tiny twin islets immersed in a translucent turquoise sea.

Cycladic Islands Charter Itineraries Highlights

Places to see

  • The clifftop villages of Oia and Fira overlooking Santorini’s caldera
  • UNESCO-listed Delos archaeological site with its ancient temples
  • Mykonos Town’s Little Venice and windmills
  • Naxos Town’s 13th-century Venetian castle
  • Sarakiniko beach on Milos is a moonscape of smooth white volcanic rocks
  • Serifos’ quaint hilltop Chora
  • Amorgos’ cliffside whitewashed Panagia Hozoviotissa monastery.
  • Goulandris Museum of Contemporary Art on Andros.

Things to do

  • Explore archaeological sites, monasteries, and fortresses.
  • Scuba diving
  • Sea kayaking
  • Windsurfing
  • Hiking
  • Cycling
  • Wine tasting (be sure to sample Santorini’s Assyrtiko and Nykteri whites)
  • Gourmet dining (notably on Santorini)
  • Late-night partying (especially on Mykonos)

Athens to Athens Itinerary

Athens to Athens Itinerary
Please note that this Athens to Athens itinerary is only a sample. The final route will be decided on board in coordination with your Captain, who will help tailor-make the...


Athens to Mykonos Itinerary

Athens to Mykonos Itinerary
This Athens to Mykonos itinerary highlights many of the beautiful Greek Cyclades islands. You and your Captain will discuss your interests and desires for your holiday. Together, you will create...


Mykonos to Mykonos Itinerary

Mykonos to Mykonos Itinerary
On this sample Mykonos to Mykonos Itinerary, you'll cruise approximately 270 nautical miles to different and unique Cyclades Islands. Although this is just a sample, you'll get an idea of...


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