Little Symi has the prettiest port in Greece. As you round the headland, neoclassical mansions in every shade of apricot and peach rise like a mirage from the sea. Built by 19th-century sponge and spice merchants, the whole town is now a national monument. You need strong legs to explore - it's about 500 steps up to the crumbling acropolis - but you won't need a car. The only proper road peters out at Panormitis monastery, a major pilgrimage site. Ravishing beaches such as Ayios Yorgos Disalonas (backed by monumental cliffs) and Marathounda (where goats will try to filch your picnic) are only accessible by boat or on foot. In the rugged hinterland, more than 100 monasteries are hidden among the pine and cypress forests.
The almighty church has kept nightlife in check. If you must see and be seen, head to quietly glamorous Astivi or Stoa bar, on miniature Agia Lesvias square, in Hora. Beach life is generally languid and low-key; Psili Ammos and Livadi Geranou are our favourite hideouts. Dinner reservations are essential at Benetos, for Med-Asian fusion on an organic farm, and Lambi for grilled fish on a purple pebble beach.