The island's main port and capital, Chora is the hot-spot for shopping, dining, and cultural pursuits. With its scenic cascade of white houses running down from the Venetian castle atop the hill, windmills, museums, and a plethora of photo-ready locations, it is certainly not to be missed.
A mere kilometer south of Chora lies the village of Pera Gialos, which used to be the island's main port. Today it boasts a relatively well-developed tourist infrastructure and a charming beach, ideal for a refreshing swim. Boat tours run from here to nearby sites and other beaches.
The scenic hilltop Venetian castle in the island's Hora is certainly worth the climb - although little remains of the castle itself, views that uncover from here are simply spectacular, with an avalanche of whitewashed houses leading down to the cerulean waters of the Aegean.
Drakos Cave, or "cave of the dragon" is a natural cave bedecked with stalactites and stalagmites in the island's north (not far from the village of Vathi). The color of these whimsical rock formations changes depending on the mineral content of the water, which makes each visit unlike the other.
The compact yet informative archaeological museum of Astypalaia provides visitors with a brief overview of the rare finds made on the island. Exhibits include jewellery, tools, ceramics, and other items dating back to the prehistoric period all the way through to Medieval times.
Perched on top of a scenic hill right beneath the Venetian castle in the island's Chora, the Panagia Portaitissa church embodies the iconic Greek white-with-a-blue-dome, postcard-ready look that dominates photographs coming from this part of the world. The structure dates back to the 18th century.
The seaside resort of Maltezana (named after Maltese pirates who used the island as their hideaway) is where many of vacationers to Astypalaia choose to stay. Some of the must-see attractions include the Hellenic Talaras Baths, ruins of an early-Christian basilica, and the ancient Analipsi church.
The shape of the shoreline near the village of Vathi makes its waters appear a stunning crystal-blue color. In and around the village, see the whimsical rock formations of the Drakos Cave, the remains of an ancient Minoan settlement at their entrance, and the lost lake of Chameni Limni, and
A mere two kilometers outside of Chora lies the small village of Livadia, set directly by the seaside in a valley where citrus groves border on lush vineyards. Not to be missed in the vicinity are the Negros Cave in Vatses (reachabale by boat from Chora) and the Agios Vasileios hilltop ruins.
Two km southwest of Chora lies the small village of Livadia, set directly by the seaside. The beach here is rather well-maintained, and various tourist facilities are available in abundance. There are several secluded coves as well as one long stretch of beach, where water sports are often played.
Pera Gialos (walking distance from Chora) boasts a relatively well-developed tourist infrastructure and a charming beach, ideal for a refreshing swim and snorkeling. There are plenty of cafes and tavernas in the vicinity. Boat tours run from here to nearby sites and other beaches.
One of the settlements most favored by tourists, Maltezana boasts a lengthy shoreline that is made up of several secluded coves and one stretch of pebbly sand beach. Some of the must-see attractions include the Hellenic Baths, ruins of an early-Christian basilica, and the ancient Analipsi church.
This pebbled, virgin beach is located at a substantial distance from Chora, and is the perfect spot for those seeking privacy away from tourist crowds. There are next to no facilities; however, reaching the beach was recently made easy via a freshly asphalted road that runs through the island.
Tzanaki, a small, secluded bay with crystal-clear waters not far from the touristy village of Livadia, is the island's official nudist beach. Due to its sheltered positioning, it is well-protected from the wind. To reach the beach, take a short (approximately 25 minute) hike to Tzanaki from Livadia.
The shape of the shoreline nearby the village of Vathi makes its waters appear a stunning crystal-blue color. Although the beach is very compact, it is ideal for those looking to escape the touristy area of Chora (located at a distance of 21km). Rooms for hire are available in the village.
Located by the Maltezana waterfront, this contemporary Greek restaurant serves elegant dishes of local cuisine on a scenic terrace with direct views over the water. An emphasis is placed on dishes containing fresh seafood. Service is above par, with an exceptionally welcoming owner Thanasis.
Located in Astypalaia's old harbor with seating directly on the beach, Mezedopolio Anastasia gives guests the opportunity to sink their feet into the sand as they tuck into a selection of delicious small meze dishes. From here, direct view of the Astypalaia castle and Chora hill unfolds.
Located at the upscale Pylaia Hotel, the Plori Bar & Restaurant is an elegant establishment offering a selection of exquisitely crafted dishes (with locally-sourced ingredients) and drinks. The outdoor terrace set on a cliff hanging over the Aegean makes for brilliant views and a unique ambiance.
Located at the beachfront in Livadia, Astropelos specializes in (perhaps, expectedly so) fish and seafood dishes. There is no menu at the restaurant, which means the owner and staff make recommendations based on what is freshly available that day. Dishes are well-crafted and beautifully presented.
The restaurant is located in the island's Chora, in a well-sheltered place with a courtyard (a great advantage for low-season windy weather). The establishment is rather popular with locals and visitors, and gets quite busy in the evenings. Serves a wide selection of meat and seafood dishes.
The well-managed restaurant, located just by the old Analipsi harbour, serves traditional local fare with a modern twist on its multiple seafood dishes. Arrive in early evening and watch local fishermen prepare boats and nets for the next morning's fishing trip on the beach directly outside.
Ageri is a great choice for dining out in Chora - the quality-to-price ratio is nearly unbeatable for a location as central as this one (the restaurant sits right next to the line-up of the iconic white windmills), and the selection of dishes is pleasant, too (try the lobster & spaghetti combo).
Fresh grilled squid (calamari) is a must at this waterside eatery, and so is the lobster pasta, keftedes meatballs, the Greek salad and other succulent menu items. Portions are very generous, so one a time time might be in order. Enjoy views of the harbor with tranquil sail boats as you dine.
The restaurant located at Antzela Stoudios is a warm, family-run establishment that serves traditional Greek fare sourced from fresh local ingredients. It can accommodate large parties and sometimes hosts traditional live music nights, which makes for excellent authentic entertainment.
The little gem of a restaurant in Kaminakia Beach (arguably one of the best in Astypalaia) is run by Linda, the chef and owner, who grows her own organic vegetables and even goats (all done within plain view from the restaurant). Proximity to the beach and water are a definitive plus.
This brilliant little cafe in Maltezana is a paradise for sweet-lovers - the selection of home-made sweets and cakes is seriously impressive, and do try the specialty cake called "mille-feuille" (freshly prepared on premises). Seating available in the cosy outdoor terrace.
The pleasant cafe, located right by the Chora windmills, offers outdoor seating in the terrace and serves breakfast (the omelette enjoys a good reputation) as well as a large selection of local sweets and ice cream. Do not leave without trying the traditional "loukoumades" donuts with honey.
Kolokutha serves incredible decadent desserts - these (and the outdoor seating directly by the water) are the establishment's main draw, but small savory snacks are served as well, for those who prefer salty over sweet. At night, the venue transforms into a casual waterfront bar serving drinks.
Located on one of Astypalaia's most scenic beaches, the Steno tavern offers guests an all-day warm welcome, all in with delicious food, snacks and drinks. Some books are available to borrow from the public bookshelf to enjoy on the adjacent beach. The vibe here is very laid-back.
The cosy venue is fit for both day and night, and (despite what the name suggests) is more of a cafe bar than a proper shop. For a daytime coffee and cake, try the traditional local "mille-feuille", the "kataifi" (syrup-drenched baklava) or the custard and whipped cream "ekmek."
A rather upscale patisserie by island standards, Zafora is a pleasant bakery and sweet shop selling all manner of traditional sweets and pastries - to take away or have on directly there, on the outdoor terrace with a view. It operates all year long, in both low and high seasons.
The outdoor terrace framed with lush green trees and fragrant flowers invites for coffee and cake with a view over the stunning hill of Chora. Archipelago Cafe & Bar serves a vast array of sweets and cakes, as well as drinks after sundown when the town beautifully lights up.
The pleasant Livadi cafe bar serves coffee and offers a concise, yet comprehensive selection of various dishes and drinks, with a few great hits for breakfast foods (such as pancakes). The wood terrace by the beach is a pleasure to imbibe on, and so are the bar's sunbeds by the water.
Known as one of the louder (although still very tame compared to similar establishments on other Greek islands) places in Astypalaia, the Vatses Beach Bar plays good music, serves food and drink, and even owns a few sunbeds set out directly by the water. It's popular among the younger holidaymakers.
One of the best places to be day and night, the Al Mare Cocktail Beach Bar (located in the Agios Konstantinos village) mixes great drinks, plays pleasant music, and even serves food with many organic ingredients sourced from its back yard garden. Sunbeds are at guests' disposal.
The beautiful view unfolding from this Astypalaia location is just one of the many reasons to reserve a night for En Plo Astypalaia Cocktail & Wine Bar. Its unique ambiance has earned fame on the island and beyond. Drinks served include fine wines and cocktails.
Inviting both day and night, the centrally located (next to the scenic windmills) Mouggou Cafe is especially attractive at sundown, when views of the harbor lighting up unfold before the eyes of patrons. A few known personalities have made appearances here for an evening drink in town.
The store is easily recognisable by the design of its logo, featuring Jack Sparrow and a mermaid. Inside, the array of items includes clothing (including Thai and Indian pieces), jewellery (hand-made silver items deserve special mention), accessories, souvenirs, and other items of interest.
The small antique shop is a rare find in Astypalaia. It is packed with curiosities, ranging from household items to vintage photographs and art to clothing and jewellery. The shop also sells local and international magazines and newspapers, which makes it well-visited not by antique-lovers alone.
The small airport located not far from the village of Analipsi (Maltezana) serves only a couple of national destinations (mainly the capital city of Athens). It is located some 12 km away from Chora, the island's main settlement. During the summer, a public bus circulates between the airport and the town. To reach other destinations, transfers must be pre-arranged. Taxis may be hired directly at the airport.
Astypalaia is connected to the port of Piraeus and other neighbouring islands via ferry lines. Ferries from Piraeus depart 3 times a week, and take about 9 hours to reach the island. Ferries also run to Rhodes, Naxos, Paros, and other islands. Astypalaia's new port is located south of Chora, in Agios Andreas. Blue Star Ferries +30 22430 61224
Public buses run relatively frequently during the summer, connecting the Chora (buses stop in Chora Square) to other larger destinations throughout the island, such as Pera Gialos, Maltezana, and Livadi. During low season, however, buses are infrequent, and travelers would be better off renting a car or hiring a cab.