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. While these winds provide exciting and often fast sailing for experienced crews, they can also create challenging conditions, particularly in exposed passages between islands.

For this reason, the Cyclades are best suited to experienced sailors, especially during the peak summer months. If you're new to sailing, we do not recommend a bareboat charter in the Cyclades during the Meltemi season.

Beginner sailors may wish to consider alternative regions that offer more sheltered and forgiving sailing conditions, such as:

• The Saronic Gulf – close to Athens, well protected, and with short distances between islands
• The Ionian Islands – calm seas, gentle breezes, and a relaxed cruising environment ideal for first-time skippers or families

That said, the Cyclades can still be an excellent destination for newer sailors—but only with the support of a professional skipper. This allows you to enjoy the adventure while learning from an expert, gaining valuable skills in handling winds, navigating open waters, and understanding local sea conditions.

At Sail Connections, we’re happy to advise you on the best match for your experience level. We can arrange a qualified skipper to help you build confidence while still exploring this iconic sailing region.

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...

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 some popular islands and routes to consider when sailing the Cyclades?

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. 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...