Eugenia is very knowledgeable, kind and fantastic guide.

Santorini Highlights Tour: Villages and Vineyards
Pair hilltop villages with the wines shaped by Santorini’s soil
Sites Visited
- Oia
- Fira
- Pyrgos
- Megalochori
Included
- 5.5 hours with a PhD or MA-level expert guide
- Private car service during the duration of the tour
- Wine tasting at a local family-owned winery
Itinerary Details
You'll be picked up at your Santorini accommodation and begin exploring one of the most unique islands in the Aegean Sea with your expert guide and private driver. Upon arriving at your first stop, the picturesque village of Oia, your expert will ensure you get the famous "blue dome photo" and give a walking tour to experience its magic. You'll meander through the whitewashed alleys where your expert will surely lead you to see the 15th-century Agios Nikolaos Castle.
Moving on to the capital of Santorini, the town of Fira, you'll arrive to enjoy the clifftop location which affords views of Nea Kameni, a still-active volcanic island to the west. Regardless of the route your expert takes you on, the Three Bells of Fira will be a highlight that you'll never forget, as the Greek Catholic church is known for its blue dome, three bells, and stunning views.
At your third stop, you'll notice a shift in architecture in the town of Pyrgos, where its steep, medieval alleys are home to wine bars and tavernas, galleries, and boutiques. Pyrgos has gained the reputation of being Santorini’s hidden gem as it sits proudly on the slopes of Mount Profitis Ilias and is built amphitheatrically. Pyrgos boasts the most amazing 360 views of the entire island of Santorini.
To wrap up your overview of Santorini, you'll finish with the town of Megalochori, where you'll visit a local winery. Owned by a local family that was the first industrial winery on the island, they have a long tradition of producing wine. Including a light lunch, you'll leave your wine tasting with a new appreciation for the Greek wine region. At the conclusion of your tour, your expert will deliver you back to your Santorini accommodation in time to enjoy the stunning sunset and reminisce on the day's learnings and exceptional views.
FAQ
You will start and end at your Santorini accommodation, where you will be picked up by your private driver.
Is the cost of lunch or any tastings included in the excursion?
Yes, the tour ends in the early afternoon before peak heat, and a wine-tasting and light meal that the winery coordinates for you are included in the tour cost.
Can dietary restrictions and allergies be accommodated?
Yes, please inform us in advance of any dietary restrictions so we can ensure ample time to communicate your needs to the winery for lunch.
What if it’s raining?
Tours operate rain or shine, but in the case of inclement weather, your expert will modify the tour so more time is spent indoors. It never hurts to be prepared; we encourage keeping an eye on the weather and bringing along an umbrella, sunscreen, water, or a hat as needed.
Is this tour walking-intensive, and/or wheelchair accessible?
We do cover extensive territory on this tour. With so many steep inclines and cobblestoned streets in the towns, this tour isn’t recommended for wheelchair users. Please contact us if you have any specific questions regarding accessibility.











From iconic landmarks to tucked-away local favorites, these are the places you’ll explore and experience firsthand with your Expert.
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Local Winery
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Oia
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Pyrgos
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Fira
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Megalochori
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English-speaking expert guideTours led in English, offering you unbroken understanding throughout.
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Intentionally sized groupsA smaller group means more time for conversations and questions.
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Tickets and entrance feesAll entry tickets included (unless clearly stated otherwise).
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HeadsetsHeadsets are included on tours that need them, so every word can be heard.
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GratuitiesTips aren’t included, but we encourage tipping as a way to thank your guide after your experience.
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Food and drinkUnless booking a Food & Drink tour or tasting experience, refreshments are not included.
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Transportation to and from the meeting pointUnless noted, pre- and post-tour transport isn’t included - this service can be added by request.
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Hotel pickup or drop-offUnless noted, travel to or from accommodation isn’t included - this service can be added by request.
Make the Most of Your Tour
Some helpful advice for getting the most from your experience, from practical prep to small on-the-day tips.
- Wear comfortable footwear
- Check the weather and dress appropriately
- Bring a bottle of water (no glass)
- Feel free to ask your Expert anything
- Bring firearms or weapons
- Bring sharp objects (e.g. knives, swiss army knives, switchblades, hiking sticks)
- Dress inappropriately to enter religious sites or sacred monuments
Don’t just take our word for it
Our Santorini tours was one of the best tours of our trip to Greece! Spiros was a fantastic guide - his background and expertise in pre-history gave us such incredible context to the history of Santorini specifically and Greece in general. We learned so much from him - even after our previous tours in Athens and the Peloponnese. We saw all four towns in Greece, he guided us effectively around the bottlenecks of picture taking tourists, and we had one of our best wine tasting experiences in memory at Venetsanos Winery. Thank you for a lovely day!
Spiros was injured and unable to make it. Stiliosis filled in for him. He was excellent and modified the itinerary at our request. We could not more highly recommend him. Knew the subject very well and was very professional and responsive to our questions and requests.
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