As the small single propeller plane landed on Astypalaia in 1994, the island’s residents and visitors celebrated the historic event and vigorously applauded the pilot. This marked the beginning of Astypalaia’s transformation into a popular holiday destination. In the years since, the island has steadily gained recognition as a sought-after vacation spot.”

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Nested in the Aegean Sea, between the Cyclades and the Dodecanese islands, Astypalaia (also known as the “Butterfly of the Aegean” due to its shape) is a remote and captivating destination that draws visitors from all over. Its two “wings” are connected by a narrow strip of land just 100 meters wide, and locals affectionately refer to the island as Astropalia. Those who have fallen in love with Astypalaia and return year after year can easily rattle off a list of reasons to visit this unique and charming island.

Chora

Chora, the main town on Astypalaia, is the hub of activity on the island and boasts some of the most breathtaking architecture in the Aegean. With its small, white cubic houses, narrow streets, and numerous churches, Hora embodies the charm of the Cyclades. The contrast between the whitewashed houses with their blue shutters and the imposing stone castle that looms over the town adds to its picturesque beauty. The town square, with its historic windmills and abundance of restaurants, cafes, and bars, is a popular gathering place, and the Town Hall is located nearby. To fully experience Chora, park your car opposite the windmills and wander through the charming narrow streets.

The stone Castle

The stone castle that sits atop the highest point of Hora occupies the entire plateau, its history dating back to ancient times. Originally an acropolis, a Byzantine castle was later built on its ruins. The Venetian castle that currently stands was constructed on the remains of the Byzantine structure. From its vantage point, the castle offers sweeping views of the town and the surrounding area.

The castle was inhabited until 1953, although by that time the need to guard against pirates had long passed. Today, the castle is open to the public for free, though it could benefit from further maintenance. Visitors, both local and foreign, can be seen making their way up the winding path to the castle throughout the day. Amid the ruins of the castle, you’ll find two beautiful white churches with bright blue domes: Agios Georgios, built in 1790, and Panagia tou Kastrou (Virgin Mary of the Castle), built in the mid-19th century. Both churches are worth a visit while exploring the castle grounds.

Archaeological wealth

In addition to its numerous churches and chapels (there are a total of 365 on the island), Astypalaia also boasts a rich archaeological history. Finds from various sites around the island can be viewed at the Archaeological Museum in Pera Gialos. However, perhaps the most notable discovery on the island is the world’s only infant cemetery, located at Kylintra near Hora. Dating back to around 750 BC, the cemetery has been the subject of much interpretation, but no theory has been definitively proven. Along with its other cultural and historical attractions, the infant cemetery adds to Astypalaia’s allure as a destination for travelers interested in the past

Info: Archaeological Museum of Astypalaia, Pera Gialos, +30 22430 61500, open from Wednesday to Monday 08:30am-16:00, Entrance fee: 2€/person

The island’s beaches

Beaches

Astypalaia’s beaches are not the typical long, sandy stretches with sea umbrellas and sunbeds found on many islands. The most developed beach is Livadi, which has a number of roadside bars and restaurants that attract a crowd. Other coves and hidden beaches on the island can be harder to find and may require a good car to reach via dirt roads. Tzanaki beach is a popular destination for those seeking a more alternative experience, though it should be noted that it is a nudist beach and does not offer any services. The beach does, however, offer stunning views of the castle. Other popular beaches on the island include Kaminakia, Agios Konstantinos, and Chrisi Ammos [golden sand]. For truly memorable swimming experiences, take a boat from Pera Gialos to the nearby islands of Koutsomytis and Kounoupes.

Night life

Astypalaia’s vibrant nightlife attracts a younger crowd in their 20s and 30s. If you’re looking to stay out late, there are plenty of options to choose from.

Castro Bar, located below the castle with a view of Pera Gialos, is a staple of the island and a must-visit destination. Here, you can enjoy carefully crafted cocktails and upbeat alternative music. For a more rock, jazz, or funky vibe, head to Mylos Bar, located next to the windmills. Across from the windmills, you’ll find Sti Thea Bar, which offers a wide selection of cocktails and a breathtaking view of the castle.

Info: Castro Bar, Hora, Astypalaia, +30 694 676 12 30 / Mylos Bar, Windmills, Hora, Astypalaia, +30 694 265 72 47 / Sti Thea, Windmills, Hora, Astypalaia, +30 693 114 48 06