The Perfect Greek Island Sailing Itinerary and Where to Stay

The legendary Greek island has been the scene of many exciting moments and wild adventures over the centuries. How can you add your own sailing trip to the wealth of excitement that has happened here? Well, choosing wisely from the huge array of potential destinations is a fine start. This itinerary will take you both on land and sea as you explore the most beautiful locations while sailing the Greek Islands.


What Is the Perfect Greek Island Sailing Itinerary?


Start in Athens


You might not think of Athens when you are considering where to go on Greek yacht charters. Yet, this fascinating city is a tremendous starting point. The Greek capital is one of the oldest cities on the planet and is easily accessed from abroad. From here you can head down to the Aegean Sea on a long but enjoyable trip. It will likely be a long journey if you start from here, which is ideal if you have a lot of time to discover authentic Greece on a leisurely trip.


Cyclades Islands – Mykonos and Santorini


Elia beach

Villa Elia


With so many islands to choose from, it can be difficult to work out where to go once you get started here. Yet, there are some islands that stand out as being some of the world’s top sailing destinations.


Among these places, we can see the stunning island of Mykonos in the Cyclades island group. This is a terrific island for enjoying the beach and the culture by day, before heading out for a thrilling night out in the many restaurants and bars. Famous for being one of the prettiest islands in the world, Santorini is in the same island chain in the Southern part of the Aegean Sea. The history is palpable here, with whitewashed houses clinging to the cliffs and the huge lagoon formed by an ancient volcanic eruption.


This is a perfect place to dock if you want to get on land and treat yourself to an exceptional Greek villa experience. Villa Elia is a luxurious Mykonos villa Perched on a hill above the famous Elia beach. Its northeastern island location offers wind protection and is just a few meters from the beach. An Uber drive into town just 11km away and you have all the onshore adventure you could want while you’re docked.


Villa Elias

Villa Elias


The island has two ports and during the summer it is a hugely popular tourist spot. The popularity of this island means that finding shops, restaurants, and things to do isn’t going to be a problem. Be sure to try the unique food on offer here, with fruit and vegetables that simply don’t grow anywhere else but in the island’s ashy, volcanic soil.


The Saronic Gulf


The dazzling Saronic Gulf is another part of Greece that attracts sailors from all round the world. This part of the Aegean Sea has attractive islands such as Aegina, Poros and Salamis among its treasures. The closeness to Athens makes this a shorter sail from the capital but it is also filled with enough exciting things to do to make it worth spending as much time as you can here. From archaeological sites to beautiful ports and stunning food, there is a world of excitement to be discovered here.


Whether you love to soak yourself in history, enjoy the beaches or try out the nightlife, there is enough here to make this your favorite sailing trip ever. Once you set sail for the terrific Greek Island you will see that this is among the world’s top sailing destinations.


Feature Nicholas Turland CCL

About Christa Thompson

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Christa Thompson is the Founder and Chief Editor of The Fairytale Traveler. She started traveling the world in 2003 when she attended a summer abroad study at the University of Cambridge in England. Since then, her wanderlust has been fierce. Her three passions in life are her son, traveling, and being creative. The Fairytale Traveler brand gives Christa the opportunity to do all of these things and to live intentionally every day. "It's never too late to believe in what you love and to pursue your dreams." -Christa Thompson

1 Comments on this post

  1. Greek Islands are so beautiful, we vacationed at Skiathos Island back in 2013 and really really want to go back!

    Tabitha / Reply

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