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

Can I combine mainland ports with islands in a Greek charter itinerary?

Absolutely. One of the unique joys of a Greece sailing holiday is the ability to combine vibrant mainland ports with serenef islands, all within a single itinerary. Whether departing from Athens or another major port, you’ll find island groups such as the Saronic Gulf, Cyclades and Ionian Islands within comfortable sailing range Continue Reading...

Why book a Greek sailing holiday through Sail Connections?

With so many options for chartering a yacht in Greece, it’s a big advantage when you work with someone who truly understands the region and the boats. At Sail Connections, we combine global expertise with a personal approach Continue Reading...

What are the sailing conditions like in Greece?

Sailing conditions in Greece are as diverse as the regions themselves, making it a destination suitable for all levels of experience from relaxed family cruising to more challenging passages for seasoned sailors. Continue Reading...

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

The cost of a bareboat charter in the Greek Islands varies depending on several factors, including the season, yacht type and size, departure base, and availability at the time of booking. However, there are many ways to secure good value through discounts and flexible planning. Continue Reading...

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

In Greece, bareboat charter options include a wide range of sailing yachts (monohulls) and catamarans, offering flexibility to suit different group sizes, budgets, and sailing preferences. Continue Reading...

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

For a bareboat charter in Greece, Greek maritime regulations require a minimum of two capable crew members: one licensed skipper and one competent co-skipper. Continue Reading...

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

To charter a bareboat in Greece, the designated skipper must hold a valid sailing licence that is officially recognised by the Greek Port Authorities. This typically includes an International Certificate of Competence (ICC) or a national equivalent Continue Reading...