Each of the Greek Cyclades Islands has something to offer, whether that be enchanting landscapes, living history or extraordinary outdoor adventure. Yet with around 220 islands to explore, the choice of where to go can be a little overwhelming. Luckily, we know the very best islands to visit for every type of yachting holiday, from a rugged escape to luxurious Santorini yacht charter. Discover exactly where to go with our Cyclades sailing guide.

Coastal scenes don’t get much more dramatic than on the volcanic islands of  Milos and Santorini. Milos is one of the Greek Cyclades Islands’ best-kept secrets, offering a secluded, off-the-beaten-track escape. Those travelling by yacht will be amazed by the stunning views available from the ocean – admire the superb landscapes of the island’s south-eastern tip, including the Sikia sea cave and the majestic white cliffs of Kleftiko, and don’t miss the shipwreck at Sarakiniko Beach on the other side of the island. Nicknamed Moon beach, the rocks here look like they’ve been sculpted by lava; truly an unmissable sight.

Santorini is renowned for its postcard-perfect scenery, but to get all of this beauty with fewer crowds head to the south of the island, offering some amazing red-, black- and white-sand beaches. Head to Paralia Perissa to find the island’s longest seafront and clear, bright turquoise water perfect for swimming.

Best Cyclades Islands for history

Santorini also offers the awe-inspiring ancient site of Akrotiri: one of the most important prehistoric settlements of the Aegean, which inhabitants were forced to flee from in the 17th century B.C after severe earthquakes hit. A volcanic eruption followed, covering the entire island and town and beautifully preserving these settlements for visitors today, just like in Pompeii.

Another important stop in our Cyclades sailing guide is the island of Delos near Mykonos. According to Greek mythology, Delos was the birthplace of God Apollo and the ancient Greeks considered it a sacred place, leading them to build the Temple of Apollo. Today, this ruin still stands, acting as a fascinating window into time gone by. History buffs will also find endless spots to explore in Naxos, which was an important city-state in ancient Greece and so holds many treasures, from the Temple of Demeter to the remarkable Kouros statues in Naxos’ beautiful countryside. Those who love the buildings but don’t know anything about the actual history themselves may wish to learn more here about how Ancient Greece came to be and what made them such an incredible civilization that we are still talking about them today.

Best Cyclades Islands for hiking

For those who like to get out and about, Naxos is home to the highest viewpoint in all of the Greek Cyclades Islands and provides some truly picturesque (and truly challenging!) walks. Hike up Mount Zeus, said to be the birthplace of the God of the same name, and immerse yourself in the luscious surrounding nature. A steep hike it may be, but the breathtaking views from the top are more than worth it.

Meanwhile, the charming island of Sifnos has some easier yet still enchanting trails, featuring a hiking route network of over 100 km divided into 19 beautiful trails. We particularly love the Faros to Kastro trail, offering 4 km trail of stunning pasture fields, olive plantations and sea views on ancient pathways. Andros, just a short cruise from lively Athens, is another hiking hotspot, with a number of well-signposted and well-maintained routes showcasing beautiful panoramas of the Greek countryside.

We hope this Cyclades sailing guide has been helpful in helping you plan your perfect luxury yacht charter – the beautiful Greek islands await…