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Beginner’s Guide to Sailing the Greek Islands

Holidays in Greece


Summers in Greece are always a magical time! With its well-preserved beaches, glorious sun, and authentic local food, there is something for everyone. And who can ignore a destination like the Greek islands?

Greek Island Tours

Is a holiday in Greece ever complete without visiting the Greek islands?

With ferries making larger islands accessible, island hopping has now become a serious sport!

But imagine this, sailing on a private yacht that allows you to explore the lesser known islands, secluded beaches and more traditional villages. What an experience!


What sailing has to offer

We understand that the biggest appeal in modern travel today are the beautiful destinations and the adventures and experiences that steer clear of the stereotypical tourist, and instead have the ability to take you off the beaten track! These experiences offer immersion into the local culture and an opportunity to find hidden treasures to boast to all your friends once you return home!

Sailing offers a unique experience of serenity, freedom and unexplored adventure.

With no ferry queues to contest with, no crowds to compete with and not even hotel check-ins to be concerned about, your floating home is there, ready and waiting for you, as it accommodates your travel needs.

The only decision you need to make is where you should moor for the night - the beautiful quaint little fishing village or the buzzing port filled with restaurants and nightclubs? The possibilities are endless. Perhaps it’s a moonlight dinner on the yacht that you had in mind. Nothing like star gazing with your guests as you re-fill your glasses.

With the ultimate freedom, you can decide in the morning which small cove of turquoise, crystal-clear waters you wish to explore!

And when you’re feeling the need to chill out, allow the warmth of the sun, the lapping water and the sound of waves, to calm you and put you to sleep.

It’s the ultimate way to visit the Greek islands!

Selecting your sailing itinerary

With more than 6,000 islands and islets scattered around the Grecian waters, each boasting alluring waters and mind-blowing scenery, choosing the right islands to visit can become a challenge

So, here are my best tips to the many sailing options available.

Greek Island Tours
  • Depending on your full travel itinerary, decide where your embarking and disembarking ports will be.

  • If you are going to continue on with your travels, make sure there are relevant means of transportation to get you to the next destination – i.e. airport, ferry or other.

  • Avoid trying to see every island within a short period of time.

  • Greek islands are clustered in groups of islands. The easiest way to navigate these is to decide on your preferred island and then visit the surrounding islands based on your interest criteria.

  • Consider what interests you, for example nightclubs, sheltered bays and coves, lively beach bars with water sport activities, historical significance, or all of the above and select a main island accordingly.

  • Don’t over think it! Pick your main island and allow the rest to unfold as you embark on a journey of new discoveries. You will be delightfully surprised!

  • Sometimes weather conditions may determine a different navigational direction. That’s okay, just go with the flow!

  • Pack a pair of beach shoes! The soles of your feet will thank you when walking on pebbled beaches.


What to expect sailing the Greek Islands for the first time

With a total coastline length of 16,000 km offering a diversified landscape. The Greek coast offers many natural attractions; from pristine picture-perfect beaches, coastal caves to mountain ranges including volcanoes. You can be confident that you’ll be pleasantly surprised! And just like a long lost relative, the island’s cultural charm and authentic tradition will welcome you home.

As a first sailing experience, the islands close to Athens are a perfect consideration.

There are many to choose from and the sail time is relatively short. With each island’s unique personality, you can be sure your island hoping experience will be memorable.


Boat selection

There are many different types of boats available for sailing.

Greek Island Tours

The mono hull sailboats are more traditional and most common. My personal preference is the catamaran!

Keep in mind that the size and style of boat for your travels will depend on your travel companions and your interests. Other things to consider as well are the cabins and bed configuration. For example, is it important to have your own private bathroom?

Often times, you might have your heart set on a sailing experience but are concerned your budget won’t afford you the sailing experiences you’ve envisaged.


A simple solution to make all your travel plans align is to consider the age of the boat selected.

A slightly older vessel can significantly reduce costs without compromising on quality. That’s a win-win in my eyes!

On the other end of the scale, there are also the motor boats.

Sailboat Hires

Greek Island Tours

Sailboat hires are typically in weekly blocks from Saturday to Saturday.

If you are interested in a 10-day hire, depending on the season, you will most likely be charged for two weeks boat hire and daily skipper usage (if required).


I hope you find this guide useful to start planning your next sailing holiday in Greece.

Knowing these valuable nuggets of information will help you take the guesswork out of your next holiday planning.

That’s what we do at Magical Sunset! It’s all about providing you with unique options to plan your once-in-a-lifetime holidays in Greece.

And what can be more unique than reliving the age-old stories of Greek gods and visiting the very same places where mythical adventures took place?

Wouldn’t it be nice to have a knowledgeable local share with you the mythical world of Greece?

Here are two of our UPCOMING TOURS to get you inspired:

Happy Holidays!

Comments and feedback are welcome!


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