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Bygone eras have left a tangible mark on ancient Astypalaia - the Venetian Castle (dating back to the 13th century) perched on top of the hill in Chora monumentalizes the Guerini family's Venetian rule that lasted (nearly uninterrupted) from 1204 all the way through to 1537. This long Venetian period was followed by a comparable stretch of Turkish presence on the Dodecanese islands - Turks left in the early 20th century, only to give way to a sequence of conquerors - the British, Italians, and Germans all enjoyed a brief presence in Astypalaia before the island was eventually back under Greek jurisdiction in 1948. Astypalaia today is a treasure ground of ancient architectural remains, scenic spots, and secluded beaches. The island's remote charm comes at a price of little to no infrastructure, especially in the outlying areas, but the trade-off is certainly worth its unparalleled tranquility and pristine quality. Thanks to the island's longstanding fishing tradition and incredible marine wealth, fish and seafood are abundant in local taverns (along with home-grown, organic produce), which are aplenty in the settlements of Chora, nearby the port of Pera Gialos, travelers' darling Maltezana (Analipsi), and the tiny villages of Livadia and Vathi.

There is plenty to do and see in and around the island. Those who dare venture out of the island's attractive, well-groomed Chora will be duly rewarded with nature trails, secluded coves and beaches, remains of ancient structures, and a rare sense of discovery in virgin lands. Heading even further out, smaller islands very close to Astypalaia are perfectly reachable by boat (tours are offered throughout, especially during high season).

Unlike some other Greek islands in the Aegean, Astypalaia cannot boast a tourist infrastructure quite as developed as its cousins'. In larger settlements (such the Chora, Maltezana, and Livadia), the beaches are usually well-kept and equipped with umbrellas and sunbeds; venturing further out, to the roads less traveled, may often mean not having as much as a one-horse town tavern in the vicinity.

For an island of slightly over a 1000 inhabitants, Astypalaia boasts a surprising number of pleasant restaurants and cafes, most of which concentrated in Chora and along the Pera Gialos waterfront. Seafood reigns queen in the menus of local eateries, with heavy culinary influences from the Greek mainland, Italy and Turkey. Do not be surprised to find that some places may not have a written down list of dishes, but rather a "spoken" menu, where the owner and/or staff announce the offers of the day.

Bakeries, coffee shops and cafes are all to be found on the relatively compact island (the likelihood of stumbling into one increases dramatically in Chora and Pera Gialos). Many beachfront establishments double as bars and cafes/restaurants, and often grant customers free access to sunbeds and umbrellas.

Nightlife in Astypalaia is rather low-key, with most evening entertainment had in the form of dinner and drinks at the local taverns (do try the local wine and spirits). Some establishments host small traditional music and dance shows, and those who prefer to part-take in dancing themselves can check out the Chora-based Kouros Bar and Club and/or the out-of-the-way Vatses Beach Bar popular with the younger crowd. Keep in mind, however, that venues are often short-lived and there is no guarantee they will re-open the following summer season.

Although Astypalaia might not exactly fit the definition of a shopper's paradise, heading to the island's Chora is a safe bet when it comes to shopping opportunities. A good take-home local specialty is a bottle of traditional ouzo, raki, or regional wine along with deli items and olive-derived products (ranging from olive oil to organic cosmetics).

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