The Cyclades offer a rich variety of islands to explore, from world-famous destinations to hidden gems. Whether you're after lively nightlife, traditional villages, dramatic landscapes, or tranquil anchorages, there's an itinerary to suit your style of sailing holiday.

Among the most popular islands in the Cyclades are:

• Mykonos – Known for its vibrant nightlife, chic boutiques and picturesque old town, Mykonos is a perennial favourite and a popular stop on many charter routes. Expect lots of fun and excitemment, but also the crowds.
• Santorini – Famed for its dramatic cliffs, whitewashed villages, and sunset views, Santorini is visually stunning but has a very busy and exposed harbour. Visiting by yacht requires careful planning and should be discussed with Sail Connections to assess conditions and anchorage options.

Other commonly visited islands that feature in many Cyclades itineraries include:

• Kea – The closest island to Lavrion and a convenient first or last stop.
• Kythnos – Known for its natural hot springs and quiet bays.
• Syros – A cultural hub with elegant architecture and less tourism.
• Paros and Antiparos – Offering a balance of beautiful beaches and traditional charm.
• Naxos – The largest Cycladic island, ideal for hiking, local cuisine, and cultural sites.
• Amorgos – A more rugged island with dramatic landscapes and a relaxed pace.
• Sifnos and Folegandros – Great for food lovers and those seeking a quieter, authentic island experience.

A special mention goes to the Little Cyclades—a group of smaller islands adjacent to Naxos including Koufonisia, Schinoussa, Iraklia, and Donoussa. These islands are perfect for those wanting to explore less-visited, unspoiled destinations with crystal-clear waters, charming tavernas, and scenic hiking trails. They’ve retained a laid-back atmosphere partly because they were among the last in the region to be connected to the electricity grid, helping them stay off the radar of mass tourism.

Cyclades sailing routes often include a mix of lively and remote islands, giving you the freedom to tailor your experience. Whether you prefer a circular route from Lavrion or a one-way itinerary between islands, we’ll help you plan the perfect journey based on your interests, sailing ability, and timeframe.

See also A Cyclades sailing itinerary: hidden gems from Lavrion There are just so many Greek islands!

Related FAQs

Can you give an example itinerary for the Cyclades less-visited islands

Set sail from Lavrion and experience a side of the Cyclades few tourists see. This one-week itinerary is ideal for those who prefer quiet bays, traditional villages, and authentic Greek island life—whether bareboating or with a hired skipper. Continue Reading...

Are the Cyclades Islands suitable for beginner sailors?

The Cyclades are renowned for their beauty and variety, but they’re also known for the Meltemi winds—strong northerlies that blow most consistently from late June to September. Continue Reading...

How long should a boat charter in the Cyclades typically be?

While a 7-day charter is the standard minimum and allows for a rewarding sailing experience, to truly immerse yourself in the diverse beauty of the Cyclades, a 2-week itinerary is highly recommended. Continue Reading...

What are the bareboat charter base locations for the Cyclades ?

The Cyclades are well served by several convenient charter bases, both on the mainland and within the island group itself. Continue Reading...

When is the best time to sail in the Cyclades Islands?

The prime sailing season in the Cyclades runs from late April or May through to October or early November. Each part of the season offers its own appeal depending on what kind of experience you're after. Continue Reading...

What are the typical weather conditions and winds in the Cyclades?

The Cyclades enjoy a classic Mediterranean climate, characterised by hot, dry summers and mild, wetter winters. During the sailing season, particularly from late May through September, daytime temperatures typically range between 25–32°C, with long hours of sunshine Continue Reading...

Why sail the Cyclades on a bareboat charter?

The Cyclades, scattered like gems across the Aegean Sea, offer one of the most iconic sailing experiences in the Mediterranean. Known for their whitewashed villages, blue-domed churches, and sun-drenched beaches, these islands are rich in history, character, and natural beauty. Continue Reading...