The Cyclades – Greece
Yacht Charter & Sailing Vacations

Cyclades • Where to go • When to go • What you should know • How to Book

Pearls of the Aegean

Turquoise waters, ancient ruins, and a gentle Aegean breeze sound nice? You might find yourself a little fond of the Cyclades. White-washed villages nestled atop rugged cliffs adorn this enchanting cluster of Greek islands. In the laid-back paradise of the Cyclades, time slows down and every cove holds a new secret to uncover.

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Antigua Yacht Charter and sailing vacations going ashore on a dingy


Bucket List

We are ashamed that we have not been there yet. It is certainly on our Bucket List – perhaps we are saving this location for a month-long trip because of the sheer number of islands. But one week out of Lavrion or one week out of Paros seems fun too. There are so many villages and anchorages to explore. While we have not been there, we certainly have heard amazing things about this location including from our clients.

Sailing Requirements

Cyclades Bareboat charter requirements:

Sailing Resume



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Sailing Skill Level

Knowledge – Skills – Experience:

✔ Intermediate Plus

Cyclades Yacht Charter note: Semi-long distances between islands with possible swells with the strong Meltemi winds, required good navigation skills, and required Mediterranean Moorings skills make this an Intermediate Plus knowledge, skill, and experience location.
Sailing Skill Levels ›

When to go?

The Cyclades Islands are beautiful sailing destinations from late spring to early fall. This time period provides ideal sailing conditions with warm and sunny weather, gentle winds, and calm seas. We often suggest aiming for June or September to provide a perfect balance between pleasant temperatures, fewer crowds, and the vibrant bloom of nature.


The Cyclades enjoy a Mediterranean climate characterized by hot, dry summers. June-August is peak tourist season with average daytime temperatures ranging from 82°F to 89°F  and water temperatures in the 70’s.  The moths surrounding the peak season offer less crowds, milder temperatures, and relatively warm seas.


The Cyclades offer some unique cultural aspects which adds authenticity and makes them a fascinating destination for those interested in the rip tapestry of Greek isle life.

  • The architecture of the Cyclades is instantly recognizable with its distinctive white-washed buildings with blue-domed churches and colorful accents.
  • The islands have a rich musical tradition, with local instruments like the bouzouki and baglamas.  You’ll find traditional dances such as the “syrtaki” and “hasapiko” being performed at local festivals and celebrations.
  • While Greek cuisine is celebrated throughout the country, each island in the Cyclades puts its own twist on traditional dishes.  Some of the local favorites include, “Domatokeftedes” (crispy fritters made from local tomatoes and mixed with herbs and feta cheese). Of course, there’s plenty of fresh seafood as well!

Must See & Do

  • Explore Mykonos: Wander through the iconic white-washed streets of Mykonos, known for its vibrant nightlife, charming boutiques, and stunning beaches.
  • Discover Santorini: Marvel at the breathtaking sunsets in Oia, explore the unique volcanic landscape, and sample local wines at Santorini’s renowned wineries.
  • Visit Delos: Sail to the ancient island of Delos, a UNESCO World Heritage Site, and explore its impressive archaeological ruins and ancient Greek temples.
  • Relax on Paros and Naxos Beaches: Unwind on the sandy shores of Paros and Naxos, two islands with gorgeous beaches offering opportunities for swimming, sunbathing, and water sports.
  • Hike in Amorgos: Embark on scenic hikes in Amorgos, where you can explore charming villages, Byzantine monasteries, and breathtaking viewpoints.
  • Experience Local Culture in Syros: Immerse yourself in the local culture of Syros, an island known for its neoclassical architecture, vibrant festivals, and cultural events.
  • Venture to Milos: Discover the stunning rock formations, sea caves, and unique beaches of Milos, including the famous Sarakiniko Beach with its moon-like landscape.
  • Visit Ancient Ruins in Sifnos: Explore the archaeological sites and ancient ruins in Sifnos, including the Acropolis of Agios Andreas and the ancient settlement of Kastro.
  • Play in the water! Kids will love snorkeling around here, giving them a chance to explore the vibrant underwater world.

How to get there?

There are a variety of charter bases that can serve as a starting base to sailing the Cyclades both on the mainland (Athens and Lavrio) and on the isles (Poros, Mykonos, Sifnos, etc).  Therefore, Athens International Airport (ATH) is the main gateway to the Cyclades. From there, you can either grab a taxi or transfer to the mainland bases or catch a connecting flight or ferry to the island charter basess.

The Cyclades Islands Bareboat Charter Sample Itineraries

Where to go on a Cyclades sailing vacation?

Cyclades Islands and Greece Related Blog Posts


NauticEd are expert Cyclades Islands yacht charter agents. We don’t charge you a fee and can more than likely save you money on all your sailing vacations. We search the world’s databases for over 8,000 yachts in 55 destinations. We give expert advice on where and when to go – likely, we’ve been there. Make an inquiry and book your sailing vacations through NauticEd Sailing Vacations.

Additional Notes

Sailing Skill Levels

Local Knowledge + Education: as Sailing Vacation Experts, NauticEd’s team has chartered and sailed in almost all these locations – providing you with the “local knowledge” you need when planning a sailing vacation. And, as the leader in sailing education, NauticEd assigns different skill levels based on the knowledge-theory and practical/experience needed for chartering in different sailing locations.

Recommended Knowledge-Theory Courses for chartering: Bareboat Charter Master Bundle (six bareboat and near coastal courses), Catamaran Sailing Confidence (if chartering a Cat), Yacht Charter Crew Course (for your crew).

Skill Levels notably emphasize the overall practical experience and competency that is required to sail in certain areas. Of course, the “devil’s in the details” on specifics, and we recommend you contact us when planning a sailing vacation. We’ll save you money on your vacation – which is great – but being prepared to have safe fun experiences that will last a lifetime is priceless!

• Intermediate = Near Coastal <5nm within sight of land, some navigation hazards (always be aware), and generally mild weather conditions. Good seapersonship (i.e., “seamanship”) skills, knowledge, and experience apply.

• Intermediate +Plus = Near Coastal <15nm, within sight of land in clear atmospheric conditions, moderate navigation hazards, and/or challenging weather. Good seapersonship skills, knowledge, and experience apply.

• Advanced = Near Coastal <20nm, within sight of land in clear atmospheric conditions, many navigation hazards, and/or potentially difficult weather. Expert seapersonship skills, knowledge, and experience apply.

*Atmospheric conditions: from the deck of a sailboat, your “visible horizon” is about 12nm on a clear day (considering typical freeboard + your height). Visibility is decreased by haze, fog, rain, smoke, and similar atmospheric considerations. Navigating by line of sight is obviously greater if your destination has features such as mountains, lighthouses, tall buildings, etc…

*Navigational hazards may include features such as rocks, shoals, rough inlets or anchorages, challenging tides and currents, lee shores, commercial traffic, etc…

*Weather: examples of challenging or difficult weather include thunder/lightning storms, areas prone to high winds, or even seasonal risks such as excessive heat.