5 of the best Greek islands for sailing

Greek island hopping is on many people’s bucket lists. Whether in your own boat or a rental, there really is no better way to explore and enjoy the islands than by sea. If you’re a keen sailor, then you may also be wondering where to buy property to use as a base for regular sailing holidays in Greece.

So, we’ve whittled 6,000 down to five and have created a list of the best Greek islands for sailing.

Thassos

The island of Thassos lies just off the Greek mainland in the Aegean Sea. Peaceful and refreshingly authentic, Thassos is a wonderful island to sail around with plenty to see.

Stop near the small island of Panagia and you might be lucky enough to see some dolphins, or take a rest break at the beautiful Aliki beach and tuck into some traditional Greek food at the popular Archodissa tavern.

While you’re on the water you can admire the island’s scenery, which is fantastically Greek. The gentle hillsides are blanketed with vineyards, olive groves and quaint villages while the beaches are vast and golden. Thassos town has a small harbour to moor up in at the end of the day and is filled with remnants of its long and interesting past. Historical highlights include an acropolis and a Roman amphitheatre.

When it comes to buying property on the island, you can find two-bedroom apartments from around €60,000 and houses from around €150,000.

Crete

Crete is the southernmost part of Greece and the largest island. It has long been popular with expats and holidaymakers who fondly speak of the friendly locals, idyllic beaches, and historical sites.

While the island caters for many hobbies and interests, sailing is where it comes into its own. When at sea you can explore the secret coves and hidden beaches, then dock up at one of the many marinas and discover the charm of the island by foot. Some of our favourite ports include Sitia Marina, Heraklion Marina, Kissamos Marina and Port of Chania.

The island of Crete is divided into four regions: Heraklion, Chania, Rethymno and Lassiti. Heraklion is home to several popular tourist destinations – including Khersonissos, Malia, Stalida and Agia Pelayga – whereas Chania is extremely green and where you’ll find the impressive Samaria canyon and its 18km trekking route. Rethymno and Lassiti also have much to offer overseas buyers.

Property on the island varies depending on where you buy, with Heraklion being the most expensive region. Two-bedroom villas there tend to cost around €300,000, but you could find the same size property for a lot less in Rethymno.

Mykonos

Globally renowned for its pretty whitewashed houses, cosmopolitan atmosphere and lively nightlife, Mykonos is probably one of the most well-known Greek islands.

The island is brimming with beaches, and the gorgeous turquoise waters of the Aegean Sea makes for a wonderful sailing destination. Popular sailing routes from and around the island include visiting the uninhabited islands of Rhenia and Delos where you can swim and snorkel amongst the sparkling coves.

Due to its popularity and desirability, Mykonos is not cheap. In the most sought-after areas particularly, such as on the west coast, many properties can be well over €1million. That’s not to say there aren’t more affordable options, you just might have to look further inland and perhaps sacrifice a pool – but with your own boat and endless access to the ocean, this might not be a dealbreaker!

Corfu

Part of the Ionian island clan, Corfu offers a delightful and scenic sailing itinerary. Cruise past soft sandy beaches and picturesque fishing villages, enjoying the tranquil environment, or stop off and take a dip in the calm, transparent waters.

The island is the perfect base to island hop down to Paxos and Anti-Paxos. Emerald Bay on Anti-Paxos is a real gem (excuse the pun!) and has been likened to the Caribbean due to its white sand and clear blue waters.

Alternatively, stay close to the shores of Corfu and bask in the island’s olive and pine groves and sheltered sandy bays.

Once again, property prices can vary depending on where on the island you choose to buy. The northwest corner of the island nicknamed “Kensington On Sea”, may give you an idea of the usual clientele and prices there, however, head towards the centre of the island and there are plenty of older properties awaiting renovation that are far cheaper. Do remember that in places Corfu is only three or four miles wide, so you would never be too far from the sea.

Santorini

Known as one of the most romantic islands of Greece with breathtaking views and jaw-dropping sunsets, Santorini is an obvious choice for a sailing holiday. Santorini is stunning, boasting blue-domed houses in that classic Greek whitewashed finish.

What makes Santorini stand out, however, is its interesting and unique collection of beaches. The island itself was formed by a huge volcanic eruption which has certainly left its mark on the landscape. As you sail around the coast, you’ll come across black pebbled beaches as well as the famous Red Beach with its vibrant red sand and rockface. The volcanic landscape has also created a number of hot springs, which are lovely to bathe in when the temperature gets a bit cooler.

Unsurprisingly, property prices are expensive. In Pyrgos, one of the larger villages on the island, for example, generally a three- to four-bedroom property will set you back around €400,000. This does mean, though, if you decide to rent out your property in the summer months, you can expect to receive a premium!