Exploring the Castle of Astypalaia

Whether you’re scaling its mountains, diving into its crystal-clear waters or strolling hand-in-hand through flower-strewn whitewashed streets, Astypalaia invites you to tap into its special energy.

The crowning glory of the main town, Chora, is the castle built by the Querini family in the 14th and 15th centuries. Among the sights to see are two blue-domed churches and spectacular views over the island’s rocky landscape.

1. Climb the Castle

The island of Astypalaia is a place that inspires wanderlust. Dubbed ‘The Butterfly of the Aegean’, it is love at first sight for many visitors thanks to its idyllic setting, crystal-clear waters, sun-drenched beaches and long heritage of hospitable residents.

The most famous sight of the island is the castle, a mesmerizing blend of Venetian and Cycladic architecture. The best time to visit it is late in the afternoon when the maze-like alleys leading up to the castle are washed in a golden light and adorned with wooden shutters.

Once upon a time, the castle served as a stronghold against pirates who plagued this part of the Aegean Sea. The castle was built with a strong, square shape with a low vaulted passageway on the southwest side. On top of it, there were a series of reinforced house walls called xokastra that formed a ring around the castle like a second line of defence.

Today, you can still see the ruins of these houses and the remains of the castle’s fortifications on the northwest side of the structure. From the castle, you can also get a good view of the entire Chora of Astypalaia with its traditional white-washed houses and charming cafes. After exploring the castle, make sure to visit the Church of Panagia Portaitissa which takes its name from a popular icon on Mount Athos and is home to a gilded iconostasis.

2. Take a Walk in the Chora

The most iconic spot on Astypalaia is the medieval castle, which towers above a town of winding streets lined with bougainvilleas and whitewashed houses. The castle’s walls have a distinctly rugged look, which gives the whole town a sense of character that makes it unlike any other Greek island.

In the center of Chora, you’ll find a collection of traditional windmills that now house boutiques and a library. Their colorful wheels and slanted roofs are a picturesque sight, but the real draw is the views they offer from their high perch. If you go during the right time of day, you’ll also be able to catch a breathtaking sunset or sunrise.

Beyond the castle, Astypalaia’s streets form a beautiful labyrinth that is worth getting lost in. You’ll be rewarded with incredible views of the sea on one side and lush green landscapes on the other, and you’ll be able to see how local life continues to thrive in this gorgeous setting.

The best time of year to visit Astypalaia is between May-June and September-October, when temperatures are cooler and you won’t be competing with as many tourists. However, the island is still a great option during peak summer months if you plan on taking advantage of its beaches and hiking opportunities.

3. Visit the Church of Panagia Portaitissa

The Church of Panagia Portaitissa is one of the most beautiful churches in the Dodecanese and is located in Chora. It was built by Saint Anthimos in 1762 and it is dedicated to the Virgin Mary. It is a pilgrimage site as it contains a copy of the icon of Panagia Portaitissa from the Monastery of Iviron on Mount Athos. The hagiography of the Virgin is awe-inspiring, as is her riveting gaze.

The church also features a wooden carved chancel table and a wooden carved chancel screen that dates back to 1766. It is a must-see for all history buffs and art lovers. Besides, the church is adorned with numerous paintings and icons from various eras. It is also home to the Ecclesiastical Museum of Astypalaia.

In addition, the church is surrounded by traditional windmills. There are eight of them in total, and they have bright white circular bodies and red roofs. You can enjoy the views of these charming structures from the castle and even visit them at sunset for an ideal romantic setting.

On your way to the castle, you will come across a couple of traditional Greek restaurants that are worth trying out. Try Ducato Di Astypalaia, for example, and you will be impressed by its great location, delicious dishes, and friendly service. Other options are Apanemia and Kafeneio Karai, both of which offer great food at a reasonable price.

4. Enjoy the Nightlife

Astypalaia is a gorgeous island, part of the Dodecanese but with a strong Cycladic vibe. It looks like a butterfly spreading its wings in the Aegean blue and captivates travelers from all around the world with marvelous beaches, heavenly food and relaxed summer nights.

Unlike most Greek islands that attract partying crowds, Astypalaia has a more friendly and relaxing atmosphere. The locals and visitors alike follow a similar schedule: have a siesta after a long day on the beach, go out for dinner at one of the traditional tavernas and enjoy a drink or two under the stars.

When the night falls, a number of bars and cafes start to open up in Chora. Castro Bar, a local favorite, is situated underneath the castle with a beautiful view of Pera Gialos and serves carefully crafted cocktails while playing upbeat alternative music. Sti Thea Bar, located across from Castro, has a similar vibe but with rock, jazz or funky songs.

The best time to visit Astypalaia is during the summer months when the weather is warm and sunny. The island never gets too crowded and the ferries run daily from Athens. It is recommended to avoid visiting Astypalaia in mid-September when the season is ending and most of the restaurants close down. The island is still nice to explore but it will feel a bit dead.