A small, butterfly-shaped island in the popular Dodecanese group, Astypalaia remains wonderfully tranquil. This is in part because it takes a little longer to get here from Athens or other Aegean Sea islands — and also because the feel remains very much laid-back and understated. So, too, are the best places to stay in Astypalaia: all intimate, characterful hotels with fabulously friendly hosts.
Begin your explorations in coastal Chora, the island’s main town. A whitewashed collection of Cycladic-style square houses with blue-painted shutters set upon the sides of a hill, this little town is wonderful for a wander. Pop into buzzy tavernas, pick up souvenirs at artisanal shops and galleries, or pick a perch at a cafe for a mid-morning coffee. Follow narrow streets to the hilltop, where you can marvel at the remnants of the imposing Venetian Castle which still dominates the town’s skyline. The striking red-roofed windmills which line the roadside are another local landmark.
Venture a little further afield to admire the Church of Panagia Poulariani, or the Monastery fo St John with its surrounding gardens. Craggy Astypalaia is a wonderful island for keen walkers and cyclists to explore, with winding trails yielding breathtaking views. There are scenic coves for swimming and sailing, too, as well as beaches for soaking up the sunshine. You can also expect dazzling views from the private terraces and pools of the best places to stay in Astypalaia — best enjoyed with a sundowner or two!