The Most Spectacular Places to Go Sailing in Greece

Explore Symi and the rest of the Dodecanese Islands on a sailing trip around Greece
Explore Symi and the rest of the Dodecanese Islands on a sailing trip around Greece | © Hercules Milas / Alamy Stock Photo
Culture Trip Travel Team

With its consistent winds and sun-baked islands, Greece is arguably the best place in Europe to go sailing. Spend your days cruising between rocky coves with impossibly clear water and tucking into olive oil-doused mezze at one of the many waterside tavernas. Here are the top postcard-perfect places to go sailing around Greece and its islands.

Sail around Greece by chartering a yacht for the day through SamBoat, or book a full week sailing holiday with Dream Yacht Charter – no experience necessary.


Natural Feature

Boats along the harbour and pretty buildings on Poros island, with the mountains of the Peloponnese peninsula behind
© Milan Gonda / Alamy Stock Photo

There’s no need to go far to see the marvellous treasures of the Mediterranean. Depart from Athens and travel west to explore the ancient seaside villages of the Peloponnese, such as Epidaurus, or southeast towards Sounion where you can spend the night under the Temple of Poseidon. Make sure you anchor at Monemvasia – this medieval town, carved into the rocky hillside, is regarded as one of the most romantic destinations in Greece.

Argo-Saronic Islands

Natural Feature

Hydra Town harbour filled with small fishing boats, with buildings and hills in the background
© AegeanPhoto / Alamy Stock Photo

Relatively close to Athens, the Argo-Saronic (or Saronic) cluster – formed of Spetses, Poros, Aegina, Hydra and Agistri – is ideal for an easy sailing getaway close to the capital. Take the time to explore the small islands, all endowed with their own unique character. Pine-covered Poros is a charming little island next to the Peloponnese; traffic-free Hydra, with its photogenic harbour, neoclassical mansions and a plethora of little cafes and restaurants is a favourite; and Spetses is equally gorgeous with tree-lined beaches and hidden coves.


Natural Feature

Umbrellas and loungers on a sandy beach next to a harbour with boats at a resort on Crete
© Peter Titmuss / Alamy Stock Photo

Crete, the largest of the Greek islands, is an excellent choice for a sailing destination with plenty to do and see. Fewer vessels cruise this coastline compared to the Cyclades or Sporades. Not only does it boast some of the most beautiful beaches in Greece, but it was also home to one of the world’s oldest civilisations, the Minoans. Visit Knossos, where legend says King Minos once lived. Avoid sailing here during July and August when the strong meltemi winds blow through; May and June or September and October are preferable.


Natural Feature

White rocky cliffs on a peninsula, with trees on the top of the cliffs, near in Aliki in Greece
© Stelian Porojnicu / Alamy Stock Photo

If you’re sailing around Halkidiki, make sure you stop by the tranquil island of Thassos. Spot some dolphins near the island of Panagia, a protected marine ecosystem and part of the Natura 2000 network along the southern coast, or admire the impressive rock formations near Giola. Stop by Aliki for a swim and mingle with the locals at Archodissa – a small tavern serving local lamb, grilled over a wood fire, with stuffed vegetables called gemista. Continue north along the coast to Paradise Beach, before anchoring in the small harbour in Thassos town for the night.


Natural Feature

Pastel-coloured and whitewashed buildings, and boats in the harbour, in Skopelos Town
© Robert Harding Productions / robertharding / Alamy Stock Photo

Four main islands make up the Sporades: Alonissos, Skopelos, Skyros and Skiathos, with the latter being the most popular. If you’re looking for a wild escape, rugged Alonissos is far less developed and has its own protected marine park, ideal for wildlife spotting. Skopelos has its own Byzantine castle to explore, whilst Skyros offers empty beaches and secluded coves with very few tourists in sight.

Dodecanese Islands

Natural Feature

The Lindos Acropolis on top of a hill, overlooking whitewashed buildings and trees, on Rhodes
© Jan Wlodarczyk / Alamy Stock Photo

Spend a week – or longer – sailing between the Dodecanese islands. Rhodes is one of the most well-known islands – explore its Unesco-protected old town before continuing on to neighbouring Tilos and Karpathos, one of the windiest islands in the Mediterranean. Alternatively, explore Kos with its Venetian castles and glamorous resorts, as well as the mostly uninhabited islet of Levitha, and Lakki Town on Leros with its Greek-Italian fusion cuisine.

Ionian Islands

Natural Feature

A shipwreck on the sandy Navagio beach, surrounded by cliffs, on Zakynthos
© Sorin Colac / Alamy Stock Photo

Zakynthos is a sparkling gem among the Ionian Islands. Drop by the Blue Caves and famous Navagio beach, which are only accessible by boat. Then sail north to beautiful Kefalonia, which needs at least two days to truly explore. Up next are welcoming Ithaca (Ithaka) and its satellite islands, and the stunning Lefkada awaits westwards. End your journey in Corfu – dock in unassuming Paxi and Antipaxi for their fantastic beaches and secluded coves.

Cyclades Islands

Natural Feature

A whitewashed church with blue domes and a view of the sea and cliffs in Oia on Santorini
© Alpineguide / Alamy Stock Photo

For picturesque views of Greece’s whitewashed houses and blue-domed churches, head to the Cyclades. Whether you’re looking to party in Mykonos, marvel at the beauty of Santorini or escape to the wilds of Koufonisia, there’s plenty to satisfy every sailor. The birthplace of Apollo on Delos is a must-visit for history fans, while Amorgos is lined with coastal hiking paths that have panoramic views over the Aegean Sea. You won’t be able to visit all 39 islands in one trip, but you can certainly tick off a good chunk.

Hop between these idyllic Greek destinations by hiring a yacht for the day with SamBoat. Alternatively, Dream Yacht Charter rent out skippered vessels for seven day trips or longer.

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