Greece offers several distinct island groups for sailing holidays, each with its own style, scenery and cultural charm. The best islands for your yacht charter depend on your experience level, interests and the time of year you're travelling. Here’s a breakdown of the most popular regions:

Ionian Islands

Ideal for first-time charterers and families, the Ionian Sea is known for calm waters, gentle breezes and short distances between ports. Islands like Lefkada, Kefalonia and Corfu offer lush green landscapes, sheltered anchorages and charming harbour towns. The sailing is straightforward and relaxing, making this region a favourite for bareboat holidays.

Cyclades

For those seeking more adventurous sailing, the Cyclades offer spectacular Aegean beauty with classic whitewashed villages, dramatic cliffs and clear turquoise waters. Islands such as Mykonos, Paros, Naxos and Santorini are stunning. Howver they come with stronger winds, especially during the Meltemi season in July and August. Ideal for more experienced sailors or crewed charters.

Saronic Gulf

Conveniently close to Athens, this region is a perfect choice for shorter itineraries or those looking to combine sailing with historical sightseeing. Islands like Aegina, Poros, Hydra and Spetses offer a mix of culture, tavernas and quiet coves, all within easy reach of each other and the mainland.

Dodecanese Islands

Located in the southeastern Aegean near Turkey, the Dodecanese is less crowded and steeped in history. Rhodes, Kos, Symi and Patmos offer a blend of Byzantine ruins, medieval castles and colourful waterfronts. Winds are moderate and reliable with plenty of off-the-beaten-path harbours to explore.

Sporades

Further north, this lush green group includes Skiathos, Skopelos and Alonissos. Known for its natural beauty and marine parks, the Sporades is quieter than other regions and ideal for nature lovers and intermediate sailors.

Southern Peloponnese

This lesser-known region offers a rewarding alternative to more crowded Greek destinations. Sailing around the southern Peloponnese gives access to dramatic coastlines, ancient ruins and quiet fishing villages. Highlights include Kalamata, a vibrant port city known for its olives, waterfront promenade and access to the rugged Mani Peninsula, and Elafonisos, famous for its white sand beaches and crystal-clear waters. The area is well-suited to experienced sailors seeking variety and tranquillity, with reliable summer winds and fewer charter fleets.

Crete

While not a typical charter region due to distances and exposure, experienced crews can enjoy Crete as part of a longer itinerary or one-way passage from the Cyclades or Dodecanese.

At Sail Connections, we help match you with the ideal Greek sailing region based on your group, sailing experience and time of year. Whether you’re after cultural immersion, quiet bays or exhilarating sailing conditions, there’s a Greek island group that’s perfect for you.

Related FAQs

Why book a Greek sailing holiday through Sail Connections?

It’s essential to work with someone who truly understands the region and the boats Continue Reading...

What are the sailing conditions like in Greece?

Sailing conditions in Greece are as diverse as the regions themselves Continue Reading...

What are the costs associated with bareboat chartering in the Greek Islands?

The cost of chartering in the Greek Islands depends on several factors Continue Reading...

What types of yachts are available for bareboat charter in Greece?

In Greece, bareboat charter options include a wide range of boats Continue Reading...

How many experienced crew members are needed on a Greece bareboat charter?

Greek maritime regulations require at least two capable crew members Continue Reading...

What sailing qualifications are required for a bareboat charter in Greece?

The designated skipper must hold a valid, locally recognised sailing licence Continue Reading...