Experience Santorini with an Exclusive Stay at Historical Villa Santa Croce

Emporio is the other intact kasteli on Santorini alongside Pyrgos, built entirely from volcanic stone in deliberate confusion: alleyways that dead-end, vaulted passages that double back, stairs climbing to balconies that step across to the next house overhead.

The design was defensive — the labyrinth meant to disorient invaders while residents moved unseen through the village. Today, it has much the same effect on visitors, who often find themselves pleasantly lost among its winding lanes. You explore the kasteli slowly with a guide, uncovering the stories, architecture, and hidden corners of one of Santorini's most fascinating historic settlements.

Oia sits on the northern tip of Santorini, where the caldera cliff drops 120 metres into the sea and the village has become the postcard image of the island. The early hour is the only way to see it clearly.

You'll arrive before the coach groups, walk to the ruined Venetian castle at the cliff edge — damaged in the 1956 earthquake and never rebuilt — and stand for a moment in the same spot where wine merchants and shipping captains stood in the nineteenth century, when this end of the island was the centre of Aegean maritime commerce.

Most of Oia’s preserved captain’s houses belonged to men — nineteenth-century shipping magnates who made their fortunes in the island’s maritime peak. Domus K 1885 belonged to Kadio Sigalas, a woman who built her wealth and her house in an era when that was not supposed to be possible.

The interior has been preserved as it was — the rooms, the cellar, the furniture, the records — and a short wine tasting is included in the tour. After the castle ruins on the cliff, the house reframes who built the maritime nineteenth century, and whom the record tends to skip.

The Santorini caldera is the partial collapsed remnant of one of the largest volcanic eruptions in human history — the late Bronze Age explosion that buried Akrotiri and probably tipped Minoan civilisation. From sea level you read the geology in a way the cliff villages cannot show you.

The catamaran afternoon runs along the volcanic cliffs to Red Beach, anchors at the islets of Palia and Nea Kameni where geothermal water surfaces into the sea for a swim, then settles on the far side of the volcano for a meal prepared by the crew. You'll return as the villages illuminate above.