Astypalaia has all the ingredients of an enchanting and mysterious Greek island that has escaped the invasion of mass tourism. It comes complete with an imposing Venetian castle and a town on a mountaintop which has stunning views of the Mediterranean all around. Called Icthyoessa in the past (abundant in fish), the island then became Stampalia due to Venetian influences.
The main town has charming places to stay in, several good restaurants, a handful of quaint bars, and an idyllic island life. Interestingly, while Astypalaia is in the Dodecanese islands (the group of islands that Rhodes and Kos belong to), it looks more like a Cycladic island (the Santorini and Mykonos group). That said, the tourism trade luckily is nowhere near that in the above-mentioned islands, making this a destination with true ecotourism potential.
Against this backdrop, Astypalaia boasts several footpaths and some 20 hiking routes to discover and a variety of magnificent landscapes. Experienced walkers may want to hike to Negro's Grotto in Vatses in order to admire its stalagmites and stalactites. But there are easier paths such as to the monasteries of Panagia Poulariani and of Agios Ioannis (St. John). Speaking of religious attractions, the church of Our Lady of Portaitissa, considered one of the most beautiful across the Dodecanese islands.
For sea-sports lovers, there's cycling, canoeing and windsurfing on Livadi beach, shaded by the high town rock from the strong sun. There are of course other beaches that you can visit independently to canoe or windsurf. Diving and snorkeling enthusiasts will also revel in the underwater world and sea life around this island, and there is a diving club that is open in summer (will organize tours for small groups during the other months as well).
The island, which is more like two islands connected through a small land mass, has numerous beaches on all sides. Pera Gialos, Livadi, Agios Vasileios, Panormos, Agios Ioannis, Maltezana and Valani are just some the beaches around, and some are accessible only by boat. Koutsoumitis and Kounoupes beaches are highly recommended. Ask the locals which beach is best if windy, if you have children or if you're looking for secluded romantic spots. You can even sail to the small islets around the island for a swimming and snorkeling excursion in the bluest waters.
Astypalaia becomes very quiet outside summer, but fall and spring and the most delightful periods to visit if you want a quieter and almost more spiritual experience. Away from the main town, you can head to Mesa Vathi which has a gorgeous church and a good restaurant.
Across the island, sights worth visiting are the windmills and castle in the main town (Chora) has well as the ancient infant cemetery which is considered unique in the world. The archaeological museum is definitely worth a visit, housing pottery, jewelry, Mycenaean tools, and different objects of interest such as the Quirini family crest with pagan symbols. Explore its riches, meet its people, hike through its nature and you will be rewarded with an authentic Mediterranean island experience.