Sailing Holidays in Greece

There are few things in life quite as relaxing as a sailing holiday in Greece. Relaxing on a sun-soaked deck, feeling the cool mist of the Mediterranean spray up from the azure blue sea, enjoying a cool drink as you head for your next white-sand beach or lively taverna, it’s a way to really get away from it all and enjoy the slow drift of the sailing pace of life that Greece can offer.

Whether you enjoy a sailing adventure as part of an island hopping in Greece, or simply take in a single island like Santorini, Crete or Skopelos from the sea, with Not In The Guidebooks you are guaranteed to get off the beaten track and discover the real, authentic Greece thanks to our local guides and hosts.

Not only will you get to enjoy the stunning beaches, postcard-perfect sunsets and thrilling sailing experiences, but you’ll also deep-dive into traditional Greek cuisine, discover beautiful theatres and temples in spectacular locations, and quiet trails that wind there way through pine forests and rugged mountainside on walking adventures on the Greek islands.

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Adventures by sea in the Mediterranean

Greece is a country famous for its beautiful archipelagos, clear blue seas and wonderfully slow pace of life, which makes it the perfect destination for a sailing holiday. With a local skipper who can take you to the very best swimming spots, the most authentic villages, and the liveliest tavernas, an adventure by water around the Greek islands can provide you with countless magical moments.

With Not In The Guidebooks, you can combine your cruising with stunning hikes, visits to ancient ruins perched upon rugged hillsides, fishing trips and authentic lunches, traditional Greek cooking experiences with the locals and so much more, so that you actually get under the skin of local culture, and leave having had a far more rewarding travel experience than your average beach holiday.

When to go on a sailing holiday in Greece

Greece is blessed with pretty stunning, warm weather from March all the way through to November, meaning you’re almost guaranteed to be topping up that tan no matter what time you set off within those months.

But there are a few tips and tricks for arriving in just the right place at the right time, that we’ll share with you so that you can get the very best experience when you go sailing in Greece.

In the spring time, whilst the sea may be a little chilly to swim in, many islands are in bloom with multicoloured meadows of wildflowers, particularly on the Dodecanese and Cyclades islands.

The summer is the most popular time to go sailing in Greece, as the temperature of both the air and the sea warms. In the Aegean Sea, the Meltemi Winds whip up, which depending on experience can either provide a hazard or a wonderful opportunity for some great sailing. Thankfully, with Not In The Guidebooks you will only ever be sailing with a highly experienced crew.

boat and sea in skiathos

In the autumn, the sea is at its warmest and therefore at the most ideal temperature for snorkelling, and you’re likely to have to deal with far less tourists on the beach or in towns and villages.

Where to go sailing in Greece

When people say they’re going sailing in the Greek islands, anyone who knows this patchwork of land and sea would be entirely justified in asking “where exactly?”

There are around 6000 islands and islets belonging to Greece, many in completely separate seas and in regions with distinct cultural identities. That being said, virtually all of them have their merits for making the ideal location for a sailing holiday.

Whether it’s in the sailing paradise of the Dodecanese, the cultural melting pot of Crete or the ruggedly beautiful Cyclades, your hosts will get you off the beaten track to unlock the local, authentic traditions and culture that make any holiday truly memorable.

Why choose Not In The Guidebooks?

We’re passionate about helping people find the most amazing experiences on their travels, through meeting local people, exploring new places, and discovering alternative activities that make holidays special. We do this by carefully selecting partners in countries around the world who are experts in their local area, sourcing interesting people who can guide you through immersive experiences.

We’ve got local partners all across Greece, from the Mediterranean coast to the country’s touristic centre – Athens. Choosing a Not In The Guidebooks holiday in Greece means you don’t have to choose between a beach holiday or an activity-filled break, you can get the best of both worlds with a unique trip.

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