Private 4-Hour Santorini Tour: Oia, Skaros Rock & Wine Tasting

Summary

Santorini Custom Tour with Local Guide and Caldera Views

You’ll explore Santorini’s best spots—Oia’s winding lanes, Skaros Rock’s epic views, Firostefani’s famous domes, and finish with local wine overlooking the caldera—all in comfort with a friendly guide who knows every shortcut.

What’s the experience like?

The first thing that hit me stepping out in Oia was the salty breeze—mixed with a hint of fresh bread from a bakery tucked behind a blue door. We wandered those famous cobblestone paths, dodging the odd stray cat and stopping every few steps for photos (honestly, you can’t help it). Our guide, Maria, pointed out tiny art galleries I’d have missed on my own, and we even peeked into a jewelry shop where the owner chatted about her family’s history on the island. The view over the caldera? It’s not just for postcards—seeing it in person is something else.

Imerovigli came next, quieter than Oia but just as striking. The air felt cooler up here, and you could hear church bells echoing off the cliffs. We took a slow walk to Skaros Rock—Maria explained how this lava-formed lookout once kept watch for pirates (hard to imagine now with all that peace and blue sky). From the edge, you get this wild sweep of sea and volcano; I caught myself just standing there, listening to the wind and watching boats drift below.

Firostefani was a quick stop but worth it for “The Three Bells”—that iconic blue-domed church everyone snaps. There’s a little café nearby where locals sip coffee in the shade; if you’ve got time, grab an espresso and just watch life go by. Last up was Santo Wines Winery. We tasted crisp white Assyrtiko while looking out over the caldera—honestly, it’s hard to beat that combo of local wine and endless sea views. The place gets busy around sunset but mid-afternoon was relaxed; we had space to chat with staff about how volcanic soil shapes their wines.

Step-by-step itinerary

Day 1 — Santorini Highlights Tour

• Explore Oia village and Caldera views
• Walk in Imerovigli and see Mount Skaros
• Visit Firostefani and photograph The Three Bells
• Wine tasting at Santo-Wines Winery

Top questions

Is this private tour suitable for families with young children?

Absolutely! We provide infant car seats and strollers are welcome. The pace is flexible so kids can enjoy too.

Can I customize which stops we visit?

Yes! Just let your guide know your interests at booking or on the day—we’re happy to adjust the route for you.

Is there wheelchair access throughout the tour?

Our vehicles are wheelchair accessible and most stops are too. Some areas have cobblestones but we’ll help make it smooth as possible.

What kind of wines will we taste at Santo Wines?

You’ll try several local varieties like Assyrtiko and Vinsanto—staff can suggest options based on your taste preferences.

What’s included

Your private tour includes bottled water, all entrance fees and taxes, luxury air-conditioned transport (with infant seats if needed), plus full Covid-19 safety measures. Your local guide will make sure everything runs smoothly so you can just relax and enjoy Santorini.