Santorini: Venetian Castles Day Tour & Oia Sunset, Wine Tasting

Summary

Venetian castles, black sand beaches, local wine and Oia sunset

You’ll climb Pyrgos Castle for sweeping island views, wander Megalochori’s winding streets (with music if you’re lucky), swim at Perivolos black sand beach, sip wine in an old cellar near Emporio’s Venetian castle, then end up watching sunset from inside Oia’s ancient walls. It’s a full day of real moments — not just postcard shots.

What’s the experience like?

“You know this used to be the tallest thing on the island,” our guide Nikos said, patting the stone wall of Pyrgos Castle. He grinned like he had a secret. I remember the way the wind whipped around us up there — salty and a bit sharp — and how you could see all of Santorini spread out below, blue domes poking through white houses. There was an old woman selling figs by the path; she pressed one into my hand and told me something in Greek I didn’t catch. Sweetest fig I’ve ever tasted.

We squeezed through Megalochori’s crooked lanes (I almost tripped on a cat — they’re everywhere), and then ducked into Symposion, this wild little music workshop filled with lyres and old photos. I tried plucking one of the strings; sounded like a chicken sneezing. Li laughed so hard she nearly dropped her phone. We didn’t stay too long — apparently from October they skip this part — but it was enough to get a feel for how much music is woven into local stories.

The minivan rolled us past Akrotiri’s castle for a quick photo stop (the caldera view from here is unreal, even if my camera couldn’t do it justice) before we landed at Perivolos beach. Black sand gets hot fast — I learned that hopping barefoot from towel to sea — but there’s something about swimming here that feels different than other places. Maybe it’s just knowing you’re floating where volcanoes once changed everything.

Later we wandered Emporio’s tight alleys, all faded blues and yellows, until we found the Venetian castle tucked away like it was hiding from time. Our guide poured us local vinsanto in an old canava cellar; tasted like sun-dried grapes and dust and something else I can’t name but still remember. By the time we reached Oia for sunset, everyone had gone kind of quiet. The sky turned gold behind those captain’s houses and cave homes — people talk about Santorini sunsets but being inside that old castle as everything glowed felt different somehow. Can’t really explain it.

Step-by-step itinerary

Day 1 — Santorini villages and sunset tour

• Visit Pyrgos village and Venetian castle
• Drive to Megalochori and visit Symposion workshop
• Photo stop at Akrotiri castle viewpoint
• Relax and swim at Perivolos black sand beach
• Stroll Emporio village and visit Venetian castle
• Wine tasting in old canava at Emporio
• Stop in Firostefani for photos
• Explore Oia village and watch sunset
• Drive back to hotel

Top questions

How long is the Santorini Venetian Castles tour?

The tour lasts a full day with pickup in the morning and return after sunset in Oia.

Is hotel pickup included on this Santorini day trip?

Yes, free hotel pickup and drop-off are included with your booking.

Do you visit Oia at sunset during this tour?

Yes, the tour ends in Oia village where you watch sunset from inside the Venetian castle.

Is lunch included on this Santorini highlights tour?

No set lunch is included but you have free time at Perivolos beach to buy lunch or swim.

Does this tour include wine tasting?

Yes, there is a wine tasting experience in an old canava cellar near Emporio village.

Are entry fees covered on this small-group tour?

The tour includes all entry fees needed for scheduled stops.

Can children join the Symposion music workshop?

Children under 7 years cannot attend the music presentation at Symposion.

Is this Santorini day trip suitable for travelers with limited mobility?

This tour involves walking in villages and castles; not recommended for those with mobility issues or certain health conditions.

What’s included

Your day includes hotel pickup and drop-off by air-conditioned minivan, guidance throughout by a local escort, all entry fees to castles and villages along the way, plus a relaxed local wine tasting in an old canava before returning after sunset in Oia village.