Santorini Highlights Full-Day Tour with Wine Tasting

Enjoy wine with a view and discover the villages of Oia, Fira and Pyrgos

The Finer Details
This five-and-a-half-hour tour around the stunning landscapes of Santorini will help you discover three of the unique villages across the island and finish with a view of the magnificent caldera, where you'll enjoy a terrace wine tasting. The small villages dotted across Santorini showcase its traditional architecture, small Santorinian white houses, medieval architecture, labyrinthine streets, and of course, the picturesque blue domes. Accompanied by a local expert, you will learn about the volcanic history of Santorini as well as its traditions and charming local culture.

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 

Where do we meet? Where does it end?
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.
Book a Tour
Where You’ll Go

From iconic landmarks to tucked-away local favorites, these are the places you’ll explore and experience firsthand with your Expert.

  • Local Winery
  • Oia
  • Pyrgos
  • Fira
  • Megalochori
What’s Included As Standard
Here’s a look at what your tour covers, plus anything you’ll want to consider arranging separately, so you can plan with confidence.
Included
  • English-speaking expert guide
    Tours led in English, offering you unbroken understanding throughout.
  • Intentionally sized groups
    A smaller group means more time for conversations and questions.
  • Tickets and entrance fees
    All entry tickets included (unless clearly stated otherwise).
  • Headsets
    Headsets are included on tours that need them, so every word can be heard.
Excluded
  • Gratuities
    We encourage tipping as a way to thank your guide after your experience.
  • Food and drink
    Refreshments are only included during a tour when clearly noted.
  • Transportation to and from the meeting point
    Guests organize pre- and post-tour transport themselves - this service can be added by request.
  • Hotel pickup or drop-off
    Unless 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.

Dos:
  • Wear comfortable footwear
  • Check the weather and dress appropriately
  • Bring a bottle of water (no glass)
  • Feel free to ask your Expert anything
Don'ts:
  • 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
Any questions? You can always contact us.

Don’t just take our word for it

2 Reviews

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.

Let Your Curiosity Shape Your Journey

Join passionate experts on intimate walking tours that reveal a city’s unique stories, spark conversations, and leave you seeing the world—and yourself—a little differently.

Structured, never scripted

Your interests guide your Expert, leading to stories and perspectives that matter to you.

Crafted for conversation

With ten or fewer guests, ask questions, engage with your Expert, and fully immerse yourself.

Experts, not guides

Explore with 1,200+ Experts—from historians and architects to archaeologists and chefs.