The best Cyclades Islands to sail around

The Cyclades archipelago is one of the most appreciated in the world, a destination for millions of tourists who are drawn both by the stunning beaches and the lively and exuberant nightlife.

These islands are a true paradise for those who visit them by sailboat: in fact, a powerful wind called Meltemi blows throughout the archipelago from the north, reaching speeds of up to 9 knots.

There is no better way to experience a unique adventure in the Cyclades Islands than by traveling on a sailboat, planning customized and independent itineraries, free from the usual crowded and predictable organized cruises.

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Boat Rental Cyclades Islands: Book Your Next Vacation!

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Which islands belong to the Cyclades?

Located in the Aegean Sea southeast of Athens, the Cyclades consist of approximately 220 islands and islets of varying sizes arranged concentrically around Delos. Each island has something different and unique to offer, making this archipelago capable of meeting the needs of any traveler.

The main islands include Mykonos and Santorini, Naxos, Paros, Milos, Ios, Syros, Amorgos, Serifos, and Tinos, which are usually the most crowded. There are other noteworthy destinations that we will explore together in this article, so keep reading to discover which islands to visit for a relaxing vacation!

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Which is the most beautiful of the Cyclades Islands?

The beauty of the Cyclades Islands is subjective and depends on individual tastes and preferences.

Here is a list of our favorites. Sailing the Cyclades Islands is a truly unique experience, and we have decided to let you experience it with an itinerary that includes some lesser-known islands to focus on absolute relaxation and get away from the crowds of tourists who often flock to these places.

You will discover idyllic places that deserve as much attention as the fascinating Santorini, where you can enjoy landscapes and nature in complete tranquility!

- Amorgos

- Folegandros

- Sikinos

- Kythnos

- Small Cyclades 

- Antiparos

- Kea

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- Amorgos 

Amorgos is located in the eastern Cyclades and is known for its wild nature, a combination of rocky coasts and long stretches of beautiful sandy beaches, as well as the picturesque town of Hora. The crystal-clear waters invite you to take a dip immediately, and you can visit numerous caves along the coastline.

On the island, you can hike through the hills and reach breathtaking viewpoints, such as the one at the Hozoviotissa Monastery. It's impossible not to return by boat with a bottle of Rakomelo, a traditional island grappa made with cinnamon, honey, and herbs, and enjoy a glass at sunset.

Hozoviotissa Monastery, on Amorgos island.

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- Folegandros

From Amorgos, we sail south to the island of Folegandros, where massive rocks give way to stretches of the whitest sand. The island's characteristic wooden balconies and narrow alleys can be found in the town of Chora. The small town surrounds a Venetian fortress and extends toward the sea, creating a unique spectacle.

Enjoy the breathtaking view from the Church of Panagia, one of the island's most characteristic and ancient buildings. Its most beautiful beach is undoubtedly Katergò, with its black sand creating a wonderful contrast with the deep blue sea.

The city of Chora was built around the Venetian fortress.

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- Sikinos

Our itinerary continues to Sikinos, an island not very well known to tourists, which has remained untouched and wild, a paradise for those seeking peace and absolute tranquility. The two towns of Alopronia and Kastro offer excellent hospitality, and in the restaurants, you can taste some of the best typical dishes in the entire archipelago.

The unspoiled beaches of Dialiskari and Agios Gergios are must-visit destinations, as is the marvelous Black Cave, located in the northern part of the island.

The view from Alopronia's harbor, Sikinos. 

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- Kythnos

Kythnos is mainly frequented by Greek tourists who appreciate its tranquility and numerous incredibly beautiful beaches. The island has a diverse history, with findings dating back to the Neolithic and Mesolithic periods, making it the island with the oldest population in the archipelago.

It is also known that Aristotle was a frequent visitor to the capital, which he admired for its excellent administration and organization. Even the Romans unsuccessfully tried to conquer it.

The most beautiful beach is undoubtedly Kolona, an isthmus of sand connecting the mainland to the promontory in front. However, we strongly recommend visiting Aghios Stefanos, which can only be reached by boat.

The isthmus of sand forms Kolona Beach.

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- Small Cyclades 

The Eastern Small Cyclades are a group of islets that cannot be reached by planes or ferries and reserve their splendor for the few tourists who can reach them by boat. Crystal-clear waters, quiet beaches, archaeological sites, and small villages warmly welcome visitors, as they are less accustomed to mass tourism.

Keros, Iraklia, Donoussa, Koufonissia, Schinoussa, Antikeros, and Daskalio are definitely the islands not to be missed for a vacation of relaxation and tranquility.

A remote pristine bay in Keros, Small Cyclades.

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- Antiparos 

Antiparos is the smaller (but not less beautiful) sister of the more famous Paros, located in the heart of the Cyclades. While it presents all the typical features of the islands mentioned above, Antiparos is particularly famous for the cave located on Agios Ioannis Hill, characterized by ancient stalactites and stalagmites that date back more than 45 million years!

The cave is located more than 100 meters deep, and to reach it, you need to traverse 411 steps through rock formations and natural wonders. At its entrance, you will find the white chapel of Agios Ioannis, built in the 18th century.

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

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.- Kea

We continue to the northernmost island in the archipelago, Kea, which is largely arid but unique due to the presence of wind and watermills, ruins, and archaeological sites of great beauty, as well as the special hospitality typical of a humble population with many traditions.

The rugged coast is ideal for navigation, and its wild nature makes it unique to explore. The various archaeological sites absolutely require a visit, starting with the Lion of Kea: the impressive animal, carved directly into the rock, is located not far from the capital and is the protagonist of numerous legends and traditions of the island.

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Which Cyclades Island Has the Most Beautiful Beaches?

Considering the islands mentioned above, the most beautiful beach can be found on the island of Amorgos and is called Agia Anna.

It is located on the southeast coast of the island, near the Panagia Chozoviotissa Monastery, one of the most famous attractions on Amorgos. This monastery, built into the rock, offers a spectacular view of the beach and the sea.

The surrounding area is characterized by impressive cliffs and panoramic views of the coastline. The beach is mostly composed of pebbles, giving it a rustic and natural appearance, creating a charming atmosphere in contrast to the crystal-clear sea. It's perfect to reach by boat to enjoy its beauty from a unique perspective!

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When to Visit the Cyclades?

Every season is perfect for visiting the Cyclades Islands. However, if you love the lively atmosphere of summer and warm days on the beach, then this season may be the best choice for you.

Spring (April - June) is an ideal season to visit the Cyclades, as the weather is mild and pleasant. The islands are less crowded, allowing you to enjoy greater tranquility. Additionally, nature awakens, and you can witness vibrant blooms and green landscapes.

During Fall (September - November), temperatures are still pleasant, and the islands are less crowded than in summer. Furthermore, the beaches are still accessible, allowing you to enjoy a more relaxed and authentic atmosphere.

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Where to Rent a Sailboat in Greece?

A sailing trip in Greece, with or without a skipper, is undoubtedly an experience you will remember forever. The ability to customize your trip without constraints and limitations makes it a perfect vacation for those who love tranquility and direct contact with nature.

To reach the Cyclades, you can choose to depart from Athens, easily accessible from any European airport, or you can reach directly one of the main islands and rent your boat there.

With Sailogy, you can choose the option that best suits your needs. Check the availability of boats in the Cyclades Islands to plan your next dream vacation!

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