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The Santorini Greek Islands Perfect Sailing Itinerary and Where to Stay

The legendary Santorini Greek Islands have 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. 


The Santorini Greek Islands Perfect Sailing Itinerary and Where to Stay


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 city is full of historical relics and monuments yet still has a lively modern feel in the restaurants and galleries. Walk next to the sparkling clear waters on the sandy shore when you want to relax and unwind.


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.


Elia beach
Villa Elia


Cyclades Islands — Mykonos and Santorini Greek Islands


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 destination for enjoying the beach and the culture by day, before heading out for a thrilling night out in the many restaurants and bars.


Go to party on the south beaches and for more privacy and seclusion go to the beaches in the north. There are plenty of fun activities, you can parasail, ski, windsurf, jet ski, or horseback ride.


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.


Wander over the black sand beaches where the water is warmer, or through the astonishing red sand beaches, walk through visually stunning hiking trails as you reflect on the rich 4000-year-old history of this interesting area. 


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.


santorini greek
Villa Elias


The Santorini Greek island has two ports and during the summer it is a hugely popular tourist spot. The popularity of this island destination means that finding shops, restaurants, and things to do isn’t going to be a problem.


Be sure to try the unique food offered here on this Santorini Greek Island, 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 around 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.


Cliff jump into the Aegean Sea, traverse cobblestone streets on a donkey or horse, eat at one of the many yummy restaurants, there is a variety of different things to do. Nature lovers and history buffs can hike old paths from the past and visit one of the many archaeological sites. Don’t fret if you can’t pick which island to visit or what to do when you get there as any choice you make will not disappoint and will give you an experience like no other.


Whether you love to soak yourself in history, enjoy the beaches and the startlingly blue water, or try out the vibrant nightlife, there is enough to make this Santorini Greek island destination your favorite sailing trip ever. Once you set sail for the terrific Santorini Greek Islands you will see why this is among the world’s top sailing destinations. Enjoy your adventure.


Feature Nicholas Turland CCL

Christa Thompson

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

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