Santorini: Private Island Tour with Wine Tasting & Beaches

Summary

Discover Santorini’s volcanic beaches, cliffside villages, and local wines

You’ll wander Oia’s winding alleys, taste monk-made wine at Santorini’s highest point, dip your toes into volcanic sands at Red and Perissa Beaches, and share laughs with locals along the way. This private tour lets you slow down and really feel Santorini—not just see it—before heading back with sandy feet and new stories.

What’s the experience like?

“You have to try the Vinsanto,” our guide Maria said, handing me a glass that smelled like honey and dried apricots. I’d never tasted wine quite like it—sweet but not heavy—and the monks at the Monastery of Profitis Ilias make their own olive oil too (which I may or may not have dipped my finger into when nobody was looking). The view from up there is wild—windy, almost too bright, with the whole island curling below us in white and blue. Maria pointed out how you can see both coasts at once if you squint past the haze. I tried; mostly saw my own hair blowing in my eyes.

We’d started out in Oia, which is even more tangled than it looks in photos. The streets twist around each other like they’re hiding secrets—little art galleries tucked behind blue doors, old men selling figs from crates. At one point I got distracted by a cat sunbathing on a wall and nearly lost the group. Shopping here is dangerous for your wallet but good for your soul (I caved for some handmade soap that still smells like thyme weeks later). Our driver waited patiently while we wandered; no rush at all.

After that came the Red Beach—those cliffs are honestly something else, deep rusty red against this weirdly clear water. The sand’s rougher than you’d expect; it stuck to my feet for hours but felt kind of grounding after all the walking. Perissa Beach was next—black sand so hot you have to hop across it until you reach the sea. We cooled off with iced coffee from a beach shack where the owner joked about tourists melting every summer. He wasn’t wrong.

I didn’t expect to laugh so much on what I thought would be just another sightseeing tour of Santorini. Maybe it was Maria’s stories about growing up here or maybe it was just being able to take our time everywhere—no herding, no crowds breathing down your neck. There’s something about seeing an island through someone else’s eyes that makes it stick with you longer than any postcard shot ever could.

Step-by-step itinerary

Day 1 — Santorini sightseeing and wine tasting

• Visit Oia for sightseeing and shopping
• Pass by Pyrgos village and Venetian castle
• Explore Monastery of Profitis Ilias
• Taste dessert wine and local products at monastery
• Relax at Red Beach
• Enjoy Perissa Black Sand Beach
• Wine tasting at traditional winery

Top questions

How long does this private Santorini tour last?

The tour lasts approximately 5 hours from pickup to return.

Is hotel pickup included in this Santorini sightseeing tour?

Yes, pickup and return from your hotel or Fira Town (cruise port) are included.

What beaches do we visit on this day trip?

You’ll visit both Red Beach and Perissa Beach during the tour.

Is wine tasting part of this private Santorini tour?

Yes, there is a stop at a traditional winery for local wine tasting.

Are entry fees covered in the price?

All fees, admissions, and taxes are included in your booking.

Can children join this sightseeing tour?

The tour is suitable for all ages; children must be accompanied by an adult.

What type of vehicle is used for transportation?

A modern air-conditioned Mercedes-Benz minivan is used for transport.

Do we get free time to shop or explore Oia?

Yes, there’s free time in Oia for shopping or exploring at your own pace.

What’s included

Your day includes private transportation in an air-conditioned minivan with WiFi onboard, hotel or cruise port pickup and return, bottled water throughout the journey, all entry fees and taxes covered up front, plus coffee or tea—and of course a stop for local wine tasting before heading back home again.