Santorini: Oia, Pyrgos & Wine Tasting Small-Group Tour

Summary

Wander Oia’s blue domes, taste volcanic wines, climb Prophet Elias

You’ll wander Oia’s postcard streets, climb Pyrgos’ winding alleys, and stand above Santorini at Prophet Elias Monastery. If you choose the wine tasting, you’ll sip local vintages with vineyard views and maybe laugh at your own Greek pronunciation attempts. This small-group tour feels like tagging along with locals who know all the shortcuts — and care if you’re having a good time.

What’s the experience like?

I’d always seen those blue domes in Santorini photos and wondered if they looked that unreal up close. Turns out, they kind of do — but it’s the quiet in the side streets of Oia that really got me. Our guide, Eleni, waved us down a narrow alley where a cat was sunbathing on a white wall. She told us about her grandmother’s house nearby (I think she said it was the yellow one with the faded shutters), and I tried to imagine living here with the caldera just… right there every morning.

Pyrgos was next — not as famous as Oia but honestly, I liked it more. There were old men playing backgammon outside a café and the smell of coffee drifting out. We only had about twenty minutes but I managed to get lost in an alley that looped back on itself. The stones were warm under my sandals. Eleni laughed when I asked if she ever gets tired of these hills (“Never! Except maybe in August”).

We climbed up to Prophet Elias Monastery — the highest point on Santorini. The wind up there was wild, almost salty, and you could see all the way to the edge of the island. Inside, it was quiet except for our footsteps echoing off stone floors. I liked that nobody rushed us; we just stood there for a bit looking out at everything below.

The optional wine tasting surprised me — I didn’t expect much (I’m not really a wine person), but something about drinking Assyrtiko while looking over those vineyards felt right. The volcanic soil gives it this strange brightness; hard to describe unless you try it yourself. Someone in our group tried to pronounce “Vinsanto” and everyone cracked up — even the winemaker joined in.

Step-by-step itinerary

Day 1 — Santorini classic highlights and wine tasting

• Meet your guide at meeting point
• Explore Oia village streets
• Visit Prophet Elias Monastery views
• Tour Pyrgos village
• Enjoy 4-course wine tasting

Top questions

How long is the Santorini Highlights Small-Group Tour?

The classic highlight tour lasts 4.5 hours; there’s also a full-day option lasting 7 hours.

Is hotel pickup included in this Santorini day trip?

Yes, pickup is included for your convenience.

What villages are visited during this tour?

You’ll visit Oia, Pyrgos, and Emporio villages during the tour.

Is wine tasting included or optional?

The wine tasting is optional and costs €20 per person.

Does this tour visit Akrotiri Excavations?

The full-day version includes Akrotiri Excavations (entry fee not included).

How many people are in each group?

The small-group tour runs with 6–12 guests per group.

Are entry fees covered for all sites?

Bottled water and transportation are included; Akrotiri entry (€20) is extra if selected.

Is lunch provided on this tour?

No lunch is provided; however, there is an optional wine tasting experience available.

What’s included

Your day includes comfortable air-conditioned mini van transport with bottled water provided throughout. You’ll be guided by a local expert who handles all logistics from pickup to drop-off so you can focus on exploring Oia’s alleys, Pyrgos village life, panoramic monastery views—and if you opt in—Santorini’s unique volcanic wines at a renowned winery before heading back relaxed (and maybe slightly sun-kissed).