Fira and Oia receive most of the attention. The cliff-top sunsets, the blue domes, the photographs that look identical in thousands of travel broadcasts: that version of Santorini is real, but it’s also well-rehearsed. Two towns, a short drive south, offer something different: the island as it was before package tours rewrote it.
Pyrgos and Megalochori were shaped by Venetian fortifications, pirate raids and the wine trade. Its streets were built to confuse invaders, not to pose for cameras. Combined with a stop at the top of Profitis Ilias Monastery, they make for one of the most historically layered half days on the island.
Related reading: An ecotourism guide to Santorini
Explore the medieval villages of Santorini with a local driver
Do you want to see Pyrgos, Megalochori and Emporio without worrying about driving or parking?
Look for a flexible private tour or transfer service that unites these traditional santorini villages with a stop at the Prophet Elías Monastery, the highest viewpoint on the island.
A common option is a Island tour 4 to 6 hours that includes time to walk the narrow streets of Pyrgos village, Megalochori village and the medieval Castelli of Emporio, with the route adapted to your rhythm and interests.
If you prefer deepenYou can also look for itineraries that add quieter neighborhoods like Finikia Village and Vothonas Village, or combine the villages with a stop at traditional wineries for tastings.
Pyrgos: the medieval capital of Santorini
Pyrgos Kalistis – “Tower of Beauty” – stands in the form of an amphitheater on a central hill and offers views of Santorini in almost all directions. It was once the capital of the island, before that role was transferred to Fira in the modern era. What remains is a typical example of medieval architecture: narrow, labyrinthine streets, fortified walls and hidden passages and, by Santorini standards, relatively little tourism.
The town has more than 40 churches, some with blue domes that photograph well from the castle walls, others small enough to be overlooked at first step. The Theotokaki Church is among the oldest on the island, dating back to the 10th century. The Church of Panagia Eisodion, built between 1660 and 1661, stands at the highest point in Kasteli and houses Byzantine icons and a carved wooden iconostasis. Most are open only for services or by agreement with locals; walking up the alleys eventually leads you to the one that is open.
The rhythm here is different. The sounds of the village (backgammon in the local ouzeria, the occasional cat) set a rhythm some distance from the ferry port and the queues at the edge of the caldera.
Related reading: Medieval villages of Santorini: where the island finally slows down
inside the castle
Pyrgos Castle was built around 1580 during the Venetian period and is the most recent of the five fortified settlements built on Santorini. Its elevated position gave defenders a clear line of sight across the Aegean and lower plains, while its design focused on deterring pirate raids.
The maze-like structure, with low two-story houses and screened balconies, was deliberately designed to confuse anyone who managed to breach the walls. The castle had only one entrance door, which was closed at dusk. Above the entrance was a single opening through which boiling oil could be poured on anyone who came there. The settlement was also built on a network of underground passages, intended as a last refuge in case the castle fell.
Kasteli largely escaped damage from the 1956 earthquake that reshaped much of the island, which is why it remains the best preserved of Santorini’s five Venetian fortifications. Passing through it now, the geometry of the defense is still legible on the street plan: dead ends, sharp curves, no direct lines of sight.
Megalochori: the town of wine merchants
Megalochori dates back to at least the 17th century and was built around the wealth of merchants who exported Vinsanto wine across the Mediterranean. Neoclassical mansions, formerly owned by wealthy landowners and wine merchants, stand alongside cave houses and traditional dwellings along a network of winding paths that converge on the main square.
Money is visible in architecture. The high outer walls and heavy wooden doors of the older mansions were not purely aesthetic: they also provided protection against the same pirates that threatened Pyrgos, making Megalochori a place that had to defend itself while projecting prosperity.
The town square is the natural stopping point: shaded, quiet and surrounded by cafes and taverns where the pace of the afternoon is not hurried. The bell tower of the Church of the Virgin Mary rises above the square’s main alley, its six bells framed in white arches on the cobblestones below. The town is small enough that most of the roads eventually lead to the same square, which makes getting disoriented in the alleys seem harmless.
The surrounding plains are covered with vineyards producing Assyrtiko grapes and Vinsanto wine, the same trade that financed the mansions that still stand in the town. Several wineries operate within minutes of the town, including Boutari and Gavalas.
Profitis Ilias: The island from 567 meters
The Profitis Ilias Monastery stands approximately 567 meters above sea level, the highest point in Santorini, and offers views of virtually the entire island from its patio. On a clear day, the caldera, the villages and the Aegean Sea are visible at the same time.
The monastery was founded in 1711 by two monks from Pyrgos, brothers named Joachim and Gabriel. It was built to resemble a fortress: the monks of Santorini in the early 18th century had the same concern about pirates as the villagers below. For about 150 years, it functioned as an educational and economic institution: it ran a school teaching Greek language and literature during the Ottoman period and operated a trading ship through the Aegean and Mediterranean.
Some monks still live and work there today. The monastery houses a collection of rare ecclesiastical objects, handwritten books and Byzantine icons, as well as active printing, shoemaking and candle-making workshops. The monks also produce wine.
Daily evening prayers are held for anyone interested in attending; Confirm schedules before visiting. The most important day of the year is July 20, the feast of St. Elijah, when locals make the trip for the full service and vigil.
Access can be by car along a winding paved road from Pyrgos or on foot along a 2.5 km clearly signposted path from the main square of Pyrgos. The tour lasts between an hour and an hour and a half each way.
Practical information
- Getting to Pyrgos: Regular KTEL buses run from Fira Central Bus Station to Pyrgos. Take the Fira-Akrotiri route and get off at the 9th stop, which is an 8-minute walk to the town center. By car, Pyrgos is about 10 minutes southeast of Fira.
- Getting to Megalochori: Located in the southwestern part of the island, approximately 10 minutes drive from Pyrgos or 15 minutes from Fira. By bus, take the Fira-Perissa line and get off at the Megalochori stop. Parking is available near the main road next to Family Bakery.
- Profitis Ilias: No direct bus reaches the top. The nearest bus stops are on the Fira-Kamari route (stop 15) and on the Fira-Perissa route (stop 9), both about 3 km from the monastery. The 2.5km hiking route from Pyrgos is clearly signposted and takes between 60 and 75 minutes. By car, follow the paved road uphill from the center of Pyrgos village.
- What to wear: Comfortable walking shoes are needed for both the castle’s alleys and the monastery trail. Shoulders and knees must be covered to enter the monastery and any open church. Bring sun protection: there is little shade on the way to the top.
- When to go: Morning visits to Pyrgos and Megalochori avoid the warmest part of the day and the tour groups that arrive mid-morning. For Profitis Ilias, the late afternoon offers the best light and cooler temperatures for the trail. Related reading: Reasons to visit Santorini in shoulder season
- Entry costs: There is no entrance fee for the village of Pyrgos or Megalochori. The monastery does not charge admission, although donations are accepted. Some churches may be closed unless a venue can arrange access.
Frequently asked questions
Is it possible to walk between Pyrgos and Profitis Ilias Monastery?
Yes. A 2.5 km marked trail starts in the main square of Pyrgos and goes up to the monastery. The route lasts between 60 and 75 minutes each way and is moderately demanding due to the unevenness. The trail passes through bushland and vineyards and has no shade, so start early and bring water.
Is Profitis Ilias Monastery open to visitors?
The grounds and exterior of the monastery are accessible, but the interior is generally not open to the public except during daily afternoon prayers (5:00 pm to 6:30 pm) and on religious holidays, particularly July 20. A small gift shop near the entrance sells products made by the monks. Modest attire is required (shoulders and knees covered).
How much time should you leave for Pyrgos and Megalochori?
Allow 50 minutes to an hour to reach Pyrgos, including the castle and a stop at the square. Megalochori is worth 30 to 40 minutes to walk through the alleys and square. Adding Profitis Ilias as a third stop (by car, not on foot) adds about 30 to 40 minutes, including the ride and views from the summit.
Are Pyrgos and Megalochori suitable for travelers with reduced mobility?
Both villages have uneven, cobbled alleys and steps, particularly inside Pyrgos Castle. Mobility aids will struggle with sections of both. The main squares and lower streets of Megalochori are more accessible. The road to Profitis Ilias by car is completely paved.
Is there anywhere to eat in Pyrgos?
Yes. Pyrgos has a strong local food scene concentrated around the main square and the streets below the castle. Several restaurants have received national recognition. The square also has cafes open from the morning. Megalochori has a smaller selection of taverns around its own square.
What is the difference between these towns and the main tourist areas of Santorini?
Oia and Fira are largely built around the views of the caldera and the tourism infrastructure that has developed around it. Pyrgos and Megalochori predate that infrastructure: the Venetian castle of Pyrgos was designed as a fortification, and the mansions of Megalochori were built by wine merchants before the island became a tourist destination. Neither town remains undiscovered, but both operate at a noticeably slower pace and show a different physical history of the island.
