Santorini itinerary for first-timers

Pyrgos is one of Santorini's old fortified villages, built on a hill in the middle of the island with its houses wrapped in rings around the remains of a medieval castle at the top. Its stepped, whitewashed lanes, arches and many small churches feel far calmer than the caldera villages, and from the top the view takes in the whole island, both coasts and the caldera.

• Stepped lanes
• Castle at the top
• Village churches
• View over the island

Come in the morning, before the midday heat, and simply walk uphill: every lane eventually leads to the top of the village.

Fira, the island's capital, runs along the top of the caldera cliffs. Its narrow marble lanes pass churches like Saint John the Theologian, the Orthodox cathedral with its large square, and shopping streets such as Erythrou Stavrou and 25 Martiou, with terraces hanging over the drop to the sea.

• Saint John the Theologian
• Marinatou Street
• Orthodox cathedral
• Erythrou Stavrou
• Caldera terraces

The lanes along the cliff edge get very busy when cruise ships are in; the streets one row back are quieter.

At the northern end of Fira, the small chapel of Agios Stylianos sits right on the edge of the cliff, with views down to the old port and across the caldera to the volcanic islands in the middle. From here the lanes start to climb towards Firostefani, the beginning of the path to Oia.

• Agios Stylianos chapel
• View of the old port
• Caldera panorama
• Path towards Firostefani

In the evening, people gather along Fira's cliff-edge lanes to watch the sun set over the caldera, and afterwards the cathedral square and the lanes around it fill with people, music and lit-up terraces.

• Cathedral square
• Sunset over the caldera
• Evening lanes
• Street music

Fira's sunset is less crowded than Oia's, and you are already back at your base when it is over.

Just north of Fira, the path along the cliff reaches Firostefani, a small, quieter village with its own main square and some of the most open views back over Fira and the caldera. It is the first stretch of the walk to Oia and an easy one, mostly paved.

• Cliff path from Fira
• Firostefani main square
• View back over Fira

Start before nine in summer: the path has almost no shade, and the morning light is on the cliffs.

Imerovigli sits on the highest point of the caldera rim, which is why it is called the balcony of the Aegean. Its white cave houses and churches step down the cliff, and the great rock of Skaros, once the site of a medieval castle, juts out into the caldera below the village.

• Path to Imerovigli
• Caldera panorama
• Cave houses
• View of Skaros Rock

Beyond Imerovigli the path leaves the villages behind and becomes a proper hike, climbing and dipping along the bare ridge of the caldera with the sea on both sides. It passes small chapels and wide viewpoints before Oia appears ahead on the northern tip of the island.

• Open ridge path
• Views over both coasts
• Hilltop chapels
• First view of Oia

This part of the trail is unpaved, steep in places and has no shade; wear proper shoes, carry plenty of water and allow about three hours from Imerovigli.

Oia is Santorini's postcard village: marble lanes along the cliff edge, cave houses carved into the rock and the blue-domed churches seen in every photo of Greece. The walk along the caldera passes the church of Agios Georgios and the Panagia Platsani church on the way to the famous blue-dome viewpoint.

• Agios Georgios
• Panagia Platsani
• Blue dome viewpoint
• Cave houses

Oia's sunset is the island's most famous moment. From the square of the Panagia Akathistos church, the marble main street leads to the ruins of the castle at the western tip, where crowds gather to watch the sun go down over the caldera and the whitewashed houses turn gold and pink.

• Panagia Akathistos square
• Main street
• Transfiguration chapel
• Castle ruins at sunset

The castle fills up an hour before sunset in summer; a spot further along the cliff towards the windmills is calmer and has the same view.