The best Cyclades Islands to sail around

The best Cyclades Islands to sail around

A unique itinerary in the Greek islands to discover uncontaminated nature and old traditions

The Cyclades Islands are one of the most famous and appreciated archipelago of the world, the main stop for tourists that are looking for beautiful beaches as well as exciting nightlife. They are located in the Egeo Sea, south-east from Athenes, and they count around 220 islands of various sizes placed in a concentric arrangement around Delos: each island has its unique features, which makes this archipelago a must-seen for any type of tourist. 

These islands are a real paradise for those who explore them by sailboat: in fact, a notorious wind named Meltemi blows on the archipelago from North almost all year round and can hit force 9. Hence the islands that are more subjected to strong winds are those in the North, such as Andros, Tinos, Mykonos, and Paros, whilst those who are slightly more sheltered from the wind are the ones in the South, like Milos, Folegandros, Ios, and Santorini.

There's no better way of enjoying the Cyclades Islands than by boat, planning a bespoke itinerary free from the usually organized cruises, often over-crowded and obvious. In this article we won't talk about the well-known Santorini or Mykonos, instead, we'll focus on the islands less traveled by the crowds of tourists that still deserve as much attention and that will allow you to discover unspoiled places you will surely be struck by.  

Here at Sailogy, we have different deals for all types of tourists. Check our boat availability around the Cyclades Islands and plan your next dream holiday in Greece! 

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The best Cyclades Islands to visit by sailboat 

- Amorgos

- Folegandros

- Sikinos

- Kythnos

- Small Cyclades 

- Antiparos

- Kea

- Map of the Cyclades Islands itinerary

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- Amorgos 

Amorgos is located in the Eastern Cyclades and is known for its wild and uncontaminated nature, the rocky cliffs and beautiful sand beaches, as well as its picturesque capital Hora. The crystal clear waters invite you to jump right in but don't forget to visit the various caves scattered around the coast. On the island, you can walk between the hills and reach breathtaking views, such as the one from the Hozoviotissa Monastery. Before going back to your boat don't forget to buy a bottle of Rakomelo, a grappa made with cinnamon, honey, and herbs typical of this island, and enjoy it on the deck at sunset! 

Monastero di Hozoviotissa, Amorgos

Hozoviotissa Monastery, on Amorgos island.

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- Folegandros

From Amorgos, we sail down South to the island of Folegandros: huge rocks and high cliffs alternate with long beaches of white sand, and melt into the characteristic wooden balconies and narrow streets of Chora. This small city was built around a fortress erected during the Venetian period and stretches out to the sea: a truly unique sight. Enjoy the view from the Church of Panagia, one of the oldest buildings in the city. The most beautiful beach is undoubtedly Katergò, where the white sand marries the deep blue of the sea in a marvelous color palette. 

If you wish to enjoy a stress-free vacation, learn more about renting a boat with a skipper. An experienced person will be by your side throughout the holiday, providing you with useful tips as well as planning a bespoke itinerary.

La città di Chora costruita intorno alla fortezza di dominio veneziano

The city of Chora was built around the Venetian fortress.

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- Sikinos

Our itinerary continues in Sikinos, not far from Folegandros: the island is not as popular as the others so it maintained its wild nature. A paradise for those in search of quiet and absolute peace. The two cities of Alopronia and Kastro offer a warm welcome to the tourists and the restaurants make some of the best dishes of the whole archipelago. Definitely worth a visit! Don't miss the uncontaminated beaches of Dialiskari, Agios Gergios, and Katergo, as well as the Black Cave located in the southern part of the island. 

Vista del porto della città di Alopronia, Sikinos

The view from Alopronia's harbor, Sikinos. 

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- Kythnos

We are taking a quick detour off the usual routes to reach Kythnos, frequented mostly by Greek tourists who are very familiar with the island and appreciate its tranquility and stunning beaches. The island has a very interesting past: excavations have discovered a site that dates back to the Neolithic or even the Mesolithic period, making it the oldest dwelling in the Cyclades. Also, it is known that Aristotele was a regular visitor of the well-organized city and that Romans tried in vain to conquer the island. The finest beach is definitely Kolona, which is actually an isthmus of sand that connects the land and the promontory facing the island, but we strongly suggest visiting Aghios Stefanos beach, reachable only by boat.  

L'istmo di sabbia che forma la spiaggia di Kolona

The isthmus of sand forms Kolona beach.

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- Small Cyclades 

We set sail to the Small Cyclades, a tiny group of islands that are not reachable by plane or cruise and that therefore reserve their beauty only to those who can wander with their own boats. Crystal clear waters, quiet beaches, archeological sites and small towns will warmly welcome as they are not used to big crowds of tourists. Keros, Iraklia, Donoussa, Koufonissia, Schinoussa, Antikeros, and Daskalio are definitely worth a visit for a holiday of quiet and peace. 

Baia incontaminata nell'isola di Keros

A remote pristine bay in Keros, Small Cyclades.

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- Antiparos 

Antiparos is the younger sister (but definitely not less pretty) of the well-known Paros, located at the center of the Cyclades. Despite presenting characteristics similar to the other islands, Antiparos is famous for the cave on Agios Ioannis hill, which contains some of the oldest stalactites and stalagmites: the oldest one dates back to 45 million years ago! The cave is located more than 100 meters deep and to reach it you will have to trek down 411 steps between rock formations and natural spectacles. Before entering the cave, you can visit Agios Ioannis' white chapel, built in the 18th century. 

La caverna sull'isola di Antiparos

Antiparos' cave contains the oldest stalactites and stalagmites of Europe.

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.- Kea

Our exclusive sailboat itinerary ends at the northernmost island of the archipelago, Kea. It is a rocky island with narrow valleys, windmills, archeological sites, and small towns breaking its coarse landscape. Here, you will experience the exquisite cordiality and hospitality typical of humble people with great traditions. The rugged coast is perfect for sailing around and the island's wild nature will enchant every tourist. The numerous sites are definitely worth a visit, first of all, the Lion of Kea: a beautiful statue carved in the rock and connected to many island legends and customs.

Un tradizionale paesino di Kea

A traditional town on the island of Kea. 

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- Our itinerary's map

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A holiday on a sailboat, with or without a skipper, is undoubtedly an unforgettable experience. The possibility of planning an itinerary without any restraint or limitation makes it the perfect holiday for those who love tranquility and direct contact with nature. 

Sailogy offers many last-minute deals! Check our boat availability in the Cyclades Islands to plan your next amazing adventure! 

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