Superyacht Itinerary: Discovering the Greek Cyclades Islands

Written By: Naomi Chadderton

Located in the southeast of the Greek mainland in the Aegean Sea, the Cyclades are the most picture-perfect of the Greek islands, typified by their whitewashed villages with bright blue roofs, golden beaches, sparkling waters and picturesque windmills.

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From Mykonos and Santorini, which form the touristic heart of the islands, to Syros, Paros and Milos, which offer sophisticated yet slightly more lazy charter activities, each and every island is in competition for the Cyclades’ most fashionable, in-the-know destination of the moment.

To explore these magical islands by charter is a dream come true, and for those looking to wind down in the ultimate serenity, it’s the perfect way to discover its secluded anchorages and astounding natural beauty. Expect many ethereal sunset experiences best witnessed from the deck of your boat, too.

On land, there’s plenty of stellar archaeological sites and postcard-worthy beaches to explore too. Throw in a world-class food scene, a couple of renowned party destinations and calm seas, and guests can enjoy the best of Greece’s many charms.

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The Cyclades enjoys a long sailing season stretching from April through to October, with warm sunny days pretty much guaranteed from May to September. To avoid the crowds and also the most powerful of the meltmi winds, plan your charter for the shoulder months of May and June or September, when the marinas and anchorages will also be less busy. Just be sure to pay these islands a visit…


Visit Ermoupolis, the historic capital of the Cyclades, known for its Venetian and Neoclassical buildings which have deemed it one of the most beautiful towns in the region. Walk thought the town hall and Vaporia, the most picturesque and aristocratic quarter of the city where you can admire the beautifully preserved Bourgeois family mansions. Ascend to the authentic medieval village of Ano Syros for a visit to the imposing church of Saint George. For those looking for a more cultural charter experience, don’t miss Syros Film Festival at the end of July.


Mykonos is a fascinating and sophisticated meeting point for the cognoscenti. The Cycladic streets lined with windmills and whitewashed, blue-shuttered houses are also home to some of the finest restaurants and bars in the world. Chichi boutiques and hedonistic beach clubs abound. Make sure you visit ‘little Venice’, one of the most charming districts on the island. Take the yacht’s tender to the coolest restaurants and nightspots; hip beach club Scorpios will delight guests while trendy Nammos boasts an exclusive shopping village, helipad and tender dock as well as a beach club.

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Delos & Rinia

Cruise to uninhabited Delos, a sacred island considered the birthplace of Apollo, on the western side of Mykonos. It’s one of the most important historical and archaeological sites in Greece. Centuries old stone lions stand guard over ruined temples and sacred sanctuaries.  

Paros & Antiparos

Spend a day at Paros’s Naoussa Bay, an enclosed and enchanted beach located on the northern side of the island. With its calm waters, it’s the ideal spot to enjoy some water sports activities or take a ride on horseback along the seashore. As the sun sets, take a stroll around the traditional village to discover local taverns like the charming Barbarossa, serving hip Greek cuisine and Mario, where you can dine on top quality seafood.

Cruise to Antiparos for a decadent lunch at Captain Pipinos seafood taverna or Sapou before a visit to Despotiko, one of the finest uninhabited islands of the Aegean where you can explore incredible archaeological history. A swim in the secret bay of Mafalda, accessible only by yacht, rounds off a wonderful day of exploration.  

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Santorini is an enduring and popular destination on bucket lists, especially of those in love, scoring high on romance thanks to some of the most majestic and breathtaking vistas in the world. Oia village offers many gourmet restaurants, traditional fish tavernas, art galleries, jewellery and artisan boutiques as well as Santorini’s most famous sunset of all.

The island’s capital, Fira, offers an enjoyable shopping experience and a wide variety of restaurants as well as the chance to explore the Archaeological Museum of Akrotiri. For the more adventurous, a hike along the cliffs from Oia to Fira is a great way to sightsee, perhaps taking in a winery tour en route where you can taste award-winning wines.  


Milos is the island of Aphrodite, a divine paradise of endless beauty that will definitely steal your heart! Make some waves with the water toys, explore the caves of Kleftiko and the lunar landscape of Sarakiniko or simply relax while indulging in the yacht’s facilities. The nearby uninhabited island of Polyaigos offers stunning crystal clear turquoise waters for swimming. After a superb lunch on board, cruise to Adamas, the main port of Milos with its shimmering village of white houses and enjoy a walk around the well-appointed village of Appolonia.