Santorini: Private Island Tour with Local Guide & Pickup

Summary

Discover Santorini’s villages, blue domes, and wine with a guide

You’ll walk Santorini’s famous whitewashed lanes in Oia, take in sweeping caldera views from cliffside villages like Firostefani, pause at iconic blue-domed churches, then taste local wines or relax by the sea—all with a friendly local guide and private pickup. Expect laughter, real stories, and moments you’ll remember long after you leave.

What’s the experience like?

“You see that blue dome? That’s where everyone tries to get their photo,” our driver Nikos grinned as we squeezed out of the van in Oia. The air smelled faintly like sea salt and sunscreen, and honestly, I was still waking up — but the white alleys were already buzzing with couples and shopkeepers setting out postcards. We wandered through those narrow lanes, stopping every few steps because someone (okay, me) kept getting distracted by the views over the caldera. There’s something about Oia that feels both postcard-perfect and a little lived-in — laundry flapping from balconies, an old man selling figs from a crate. I tried to ask him for one in Greek; he just smiled and handed it over.

After Oia, we wound along the cliffs toward Firostefani and Imerovigli. Nikos pointed out Skaros Rock — apparently people used to build castles up there to spot pirates. The wind picked up as we got closer; you could hear church bells echoing somewhere below us. At one point, we stopped at this blue-domed church (the “Three Bells of Fira” — you’ve probably seen it on Instagram), but in real life it’s quieter than I expected. Just us, some stray cats sunning themselves on warm stone, and that ridiculous view down to the volcano.

The highest point of Santorini is Prophet Elias Monastery — it’s not far but feels like another world up there. The air is thinner and smells like wild thyme. Nikos let us wander around for a bit; I sat on a low wall just watching clouds drift over the island. We had the option to visit a winery or go to the black sand beach for lunch — we chose wine (no regrets). The tasting was relaxed; our host poured samples of Assyrtiko while telling stories about his grandfather’s vineyard. I still think about that crisp white wine when I see Santorini photos now.

Step-by-step itinerary

Day 1 — Santorini Highlights Tour

• Meet guide and travel to Oia village
• Visit Firostefani and Imerovigli villages
• Photo stop at Three Bells of Fira
• Visit Prophet Elias mountain viewpoint
• Wine tasting at traditional winery (optional)

Top questions

How long does the private Santorini sightseeing tour last?

The tour lasts approximately 4-5 hours.

Is hotel pickup included in this Santorini tour?

Yes, hotel or port pickup is included.

What villages are visited on this Santorini day trip?

You’ll visit Oia, Firostefani, and Imerovigli.

Does the tour include wine tasting?

A stop at a traditional winery for wine tasting is optional.

Can cruise ship passengers join this private tour?

Yes, cruise ship passengers can join with advance details provided.

Is lunch included in the Santorini sightseeing tour?

No set lunch is included; you can choose between winery tasting or visiting the black sand beach for lunch at your own expense.

Are entry fees or taxes included in the price?

All taxes, fees, and handling charges are included.

Is this tour suitable for all fitness levels?

Yes, it’s suitable for all physical fitness levels.

What’s included

Your day includes private transport by air-conditioned minivan with hotel or port pickup and drop-off arranged ahead of time. A local English-speaking guide leads you through each village stop—Oia, Firostefani, Imerovigli—and up to Prophet Elias Monastery. All taxes and handling fees are covered. You can choose to add a relaxed wine tasting at a traditional winery or opt for time at the black sand beach before heading back.