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Small Cyclades: Greek islands off the beaten path

Small Cyclades: Greek islands off the beaten path

Planning your next sailing holiday in Greece? Looking to stay away from the tourist traps? Don’t worry—there are still plenty of ways to enjoy an island retreat without all the crowds, and the Small Cyclades in the Greek islands are the perfect secret getaway if you’re willing to step off the beaten path. 

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What makes sailing the Small Cyclades such a dream holiday? 

Top reasons to visit Small Cyclades Islands in Greece
Traditional cafe in the Cyclades.

There’s nothing like taking off for an island retreat to catch some sun and sand and soak up the sunshine. But you’re not the only one with island life on the mind. Some locales are so hot and so noteworthy, that once you’re there … well, those crowded beaches don’t exactly make it feel like a retreat.

Everyone’s heard about partying in Mykonos, but if you’re after a holiday experience that offers a little more tranquillity and R&R, look to the lesser-known Greek islands: the Small Cyclades.

Unlike the main Cyclades, which attract millions of tourists every year, the small Cyclades are far less travelled and are a sort of “insider secret” among real travel fiends. 

Why should you visit the small Cyclades?

For one, you’ll truly be able to enjoy the serene “island life” here. The Small Cyclades are among Greece’s smallest inhabited islands with populations only in the couple hundreds. Sailing around Greek islands like these allows you to slow down, take a break from your normal hectic schedule, and really soak in the simpler, more leisurely pace of life. 

And there’s plenty to soak in. The Small Cyclades are abound with beautiful beaches, stunning hiking trails, and one-of-a-kind Mediterranean views. 

Small Cyclades best islands

Iraklia, Schinoussa, Koufonisia & Donousa are some of the best Greek islands in Small Cyclades
Iraklia, Schinoussa, Koufonisia & Donousa are some of the best Greek islands in the Small Cyclades

What’s in store for you when you decide to take a step off the beaten path and travel to the Small Cyclades? 

Iraklia is the largest island in the Small Cyclades. It’s also home to the Cave of the Sacred Icon of Agios Giannis, where you can explore stalactites and stalagmites by torchlight. Looking for a little more sun? Iraklia has eight breathtaking hiking trails whose cliffs offer perfect views of the other Greek islands.

The second most populated island in the Small Cyclades is Schinoussa. Home to ancient sites, like a Byzantine church and even a medieval castle, Schinoussa has a rich history that’s ripe for exploration. Here, you can enjoy your pick of secluded beaches, like Psili Ammos or Lioliou Beach, and then head to some of the delicious cafes and restaurants in Schinoussa’s three villages, Chora, Mersini, and Maseria. 

Looking to have the best of both worlds when sailing the Cyclades?

Koufonisia is sometimes called the Mykonos of the Small Cyclades and is probably the most popular in this stretch of smaller Greek islands. A particularly great time to go is in late May or early June when you could catch the Fisherman's Festival, a feast celebrated on Koufonisia on the Saturday before Pentecost Monday, complete with traditional music, dancing, and, of course, great food.

Donousa is another stop in the Small Cyclades that you don’t want to miss while yacht chartering Greece. The main village is called Stavros, where you can check out the Church of Stavros with its striking blue dome, explore the villages’ taverns and cafes, and spend days visiting the islands’ four main beaches. 

Preparing for your journey to the small Cyclades

Ready to travel away from the crowds for a getaway that’s 100% relaxation and nowhere near the tourist traps? 

The best time for sailing the small Cyclades is from June to mid-September when clear skies with sunshine are the norm, and you can count on an average temperature of 25C (77F). 

Next, when preparing your Cyclades sailing itinerary, there are a few things you’ll want to keep in mind. 

First, where to start from: You can begin your journey either from Lavrion, Paros, or Mykonos. Lavrion is on the mainland, so it is easily accessible from Athens International Airport. Paros and Mykonos, on the other hand, are in the heart of the Cyclades. 

Because the Small Cyclades are further from the mainland, we recommend a two-week yacht charter and larger yachts

A longer yacht charter simply gives you more time to cross the longer distance, so you’ll have more time to make stops along the way and hit the beach. 

Next, you’ll also want to consider what kind of yacht to charter for sailing the Cyclades. 

A larger yacht is key for sailing the Aegean Sea, as the Meltemi wind that blows in July and August would be too strong for smaller yachts. For your unique trip, a larger yacht might be a catamaran, which can easily cover more distances, or a larger sailing yacht if you’re looking for the ultimate and original sailing experience! 

Not sure which one’s the right fit for you?  Catamaran vs Monohull 

​​​​​​​Your small Cyclades holiday itineraries

Small Cyclades Holiday Itineraries
Top holiday itineraries in the small Cyclades

Due to the larger distances and prevailing winds, you can’t explore all of the islands in a single trip—but the Small Cyclades are such a treasure trove of travel delights, that you’ll want to come back again and again! 

Ready to brainstorm your Small Cyclades sailing journey? Check out below a few general guides for your itinerary. Of course, the final itinerary will depend on prevailing weather conditions.

Recommended 14-day Small Cyclades sailing itinerary from/to Lavrion

  • Day 1. Lavrion
  • Day 2. Kea
  • Day 3. Syros
  • Day 4. Mykonos
  • Day 5. Donousa
  • Day 6. Koufonisi
  • Day 7. Schinoussa
  • Day 8. Iraklia
  • Day 9. Paros
  • Day 10. Sifnos
  • Day 11. Serifos
  • Day 12. Kythnos
  • Day 13. Lavrion
  • Day 14. Check out

Recommended 7-day Small Cyclades sailing itinerary from/to Paros

  • Day 1. Paros
  • Day 2. Koufonisi
  • Day 3. Schinoussa
  • Day 4. Iraklia
  • Day 5. Ios
  • Day 6. Folegandros
  • Day 7. Paros

To avoid the tourist trips and truly catch some R&R on your next holiday getaway, there are few places better than the remote, tranquil paradise of the Small Cyclades. 

Need help picking your yacht charter and planning your itinerary? Get in touch with a consultant from Yacht4less for a free quote.


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