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.

With just one week, you can explore a handful of islands—typically within a limited radius of your departure base such as Lavrion, Paros, or Mykonos. You'll get a taste of island-hopping, but travel distances, weather conditions (especially if the Meltemi winds are active), and time constraints may limit how far you can venture.

A 14-day charter opens up far more possibilities. You’ll have time to reach more remote islands, sail at a more relaxed pace, linger in favourite anchorages, and adjust your plans based on weather or personal preference. This flexibility makes for a richer, more relaxed, and more rewarding sailing experience.

If you are limited to a 7 day charter, Sail Connections will tailor an itinerary to suit your timeframe and help you choose a starting base—such as Paros, Naxos, or Lavrion—that minimises travel time and maximises your enjoyment.

No matter how long you have, we’ll help you make the most of it with a carefully planned route and the right boat for your group.

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...

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...