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There are few countries in the world so closely associated with island hopping as Greece is, and it only takes a quick look at a map to see why. With around 6000 islands and islets, the Greek Mediterranean coast is a labyrinth of azure blue seas lying between points of dark-green pines, sandy beaches and atmospheric fishing villages.

Once you’ve done a little research and seen just how addictive the sailing lifestyle is in Greece – the cool sea breeze, the sun beating down on the deck, the incredible food at every island, each one with its own unique character, the only question you’ll be left asking is – when can I set sail?

Each time of the year has its own pros and cons for a Greek sailing holiday, so we’re going to give you some tips on when you should plan your bucket list island hopping experience in Greece.

Greek Sailing in Spring

greek sailing boat

Greece is blessed with beautiful weather year-round, meaning the season for sailing can run from as early as March until as late as November.

The early months of the year, which arrive as the rains have fallen over the islands in the winter, provide island hoppers with specks of lush, flower-covered meadows dotting the clear blue waters of the Aegean.

This is an ideal time to sail to the Dodecanese or the Cyclades, as the heat of the summer will make these islands drier as the year goes on.

Prices will also be a little lower in March and April, although compared to May and early June, you may find the sea a little chilly to swim in. Fortunately, most tavernas and tourist attractions will be open come the Spring months, and if you catch the country during the celebration of Greek Orthodox Easter, you’ll see the islands in the full-swing of a celebration that involved consuming pretty vast quantities of wine.

Island Hopping in the Summer

person jumping into the sea from a sailing boat in greece

The high season is the high season for a reason. Temperatures are at their highest and gloriously hot, which combined with the salt spray of the sea and a cool breeze, and a dip in the unreasonably warm sea, creates great conditions for enjoying the Mediterranean to its fullest.

All the attractions and tavernas will be open, although you should be aware of higher numbers of tourists on many islands, particularly Kos, Mykonos and Santorini.

In the Aegean Sea, you’ll have the Meltemi Winds which can either provide great sailing winds, although they can also prove hazardous for inexperienced sailors.

Accommodation and charter prices will be at their highest, but considering you’re pretty much guaranteed glorious sunshine, high temperatures and warm seas, some people would say that it’s worth setting sail in July or August.

Cruising the Med in Autumn

sunset at a monument in paros greece

September is one of the most popular times of year to go island hopping in Greece, thanks to the near-tropical sea temperatures and the lower number of tourists in the towns and on the inhabited islands.

If you’re a keen swimmer or snorkeler, this is probably the best time of year to head out and experience the beautifully clear seas and pristine beaches that lie off the beaten track in Greece.

You’ll also find that prices become a little lower as the temperatures do, although those slightly lower temperatures mean that visiting Byzantine ruins, ancient Greek temples and Roman forts becomes a little less exhausting.

Autumn is also the time of year that the locals harvest olives and grapes, and produce the traditional raki, so the freshest produce is never that far away.


Sailing holidays in Greece are magical at any time of year, and while some periods come with minor drawbacks, with Not In The Guidebooks we put you in touch with expert local guides who will ensure your island hopping experience in Greece is the bucket list holiday you’ve dreamt of.

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