Santorini Highlights Full-Day Tour with Wine Tasting

Enjoy wine with a view and discover the villages of Oia, Fira and Pyrgos
From US$1,470 privately
Book a Tour
Tour Details
5.5 hours
Product Type
  • Local Winery
  • Oia
  • Pyrgos
  • Fira
  • Megalochori
Photos & Highlights
  • Explore the highlights in the top villages in Santorini with a local expert
  • Includes a private car service
Select a date
Tour Description
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.
  • Oia
  • Fira
  • Pyrgos
  • Megalochori
  • 5.5 hours with a PhD or MA-level expert guide 
  • Private car service during the duration of the tour
  • Wine tasting at local family-owned winery

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 to your first stop, the picturesque village of Oia, where 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 destination, 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 who 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.


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, 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.
Where You'll Start
(5.0) 1 Review

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

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.