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Santorini Highlights: Pyrgos to Oia Exploration
5.0
47 Ratings
Thira
Embark on a semi-private island tour of Santorini, discovering its rich history, picturesque villages, and indulging in a wine tasting experience. Visit ancient ruins, traditional villages, and stunning Oia village with cliffside views. Includes lunch and a designated driver.
Embark on a semi-private island tour of Santorini, discovering its rich history, picturesque villages, and indulging in a wine tasting experience. Visit ancient ruins, traditional villages, and stunning Oia village with cliffside views. Includes lunch and a designated driver.
Duration:
5 hours
Cancellation:
24 hours
Highlights
- Castelli of Pyrgos - Explore Pyrgos Traditional Village, established in the 15th century by the Venetians. It stands as one of the island’s top five well-preserved castle ruins.
- Akrotiri Archaeological Site - This archaeological marvel is among the most significant prehistoric sites in the Aegean, marking the first settlement on Santorini…
- Castelli of Pyrgos - Explore Pyrgos Traditional Village, established in the 15th century by the Venetians. It stands as one of the island’s top five well-preserved castle ruins.
- Akrotiri Archaeological Site - This archaeological marvel is among the most significant prehistoric sites in the Aegean, marking the first settlement on Santorini from the Late Neolithic period (4th millennium BC).
- Megalochori - Traditional Village - Originating in the 17th century, this village was known for traders and affluent landowners who exported the renowned island wine, Vinsanto.
- Oia - Discover Oia village on foot, capturing stunning photographs of the breathtaking cliffside views.
- Santorini - Enjoy a light lunch featuring Greek traditional dishes, complemented by wine tasting at one of Santorini’s premier wineries, guided by an expert sommelier.
What's Included
- Tour is only in English
- Bottled water
- Wine Tasting
- Lunch
- Liability insurance & designated driver
- Pick up & return transfers
- Tour is only in English
- Bottled water
- Wine Tasting
- Lunch
- Liability insurance & designated driver
- Pick up & return transfers
What's Not Included
- Tickets & expert guide for Akrotiri excavations. Self-guided tickets cost 25€ per person
- To the beaches we do not have time for swimming.
- Tickets & expert guide for Akrotiri excavations. Self-guided tickets cost 25€ per person
- To the beaches we do not have time for swimming.
Additional Information
Explore Pyrgos Traditional Village, established in the 15th century by the Venetians, and recognized as one of the top five best-preserved castle ruins on the island. Discover the Akrotiri Excavation, a significant archaeological site of the Aegean, representing the earliest settlement on Santorini from the Late Neolithic period. Visit Megalochori…
Explore Pyrgos Traditional Village, established in the 15th century by the Venetians, and recognized as one of the top five best-preserved castle ruins on the island. Discover the Akrotiri Excavation, a significant archaeological site of the Aegean, representing the earliest settlement on Santorini from the Late Neolithic period. Visit Megalochori Traditional Village, which dates back to the 17th century, known for its traders and wealthy landowners who exported the renowned Vinsanto wine. Enjoy a light lunch featuring Greek traditional dishes paired with a wine tasting at one of Santorini’s premier wineries, guided by an expert sommelier.
Stroll through Oia village to capture stunning photographs of the breathtaking cliffside views.
Includes liability insurance and a designated driver.
- Travellers visiting with a cruise ship can ONLY be picked up from the “Prehistoric Museum of Thera” in Fira town.
Location
Fira Theotokopoulos Main Square
Ipapantis
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
5.0
(47 Ratings)
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Francisco
Apr 10, 2026
Excellent Santorini Island tour. - My Wife and I decided to spend our Honeymoon in Santorini. We booked a tour of the island and have no regrets. Our driver, Antonis, did a fenomenal job in showing the history of the island from the main eruption of the volcano in ~1600 BC to how it became a worldwide sensation for tourism today. When we got to the winery for our wine tasting, Antonis went above and beyond to not just explain what each wine was, but also did a deep dive into Santorini's unique, one-of-a-kind wine-making process. Antonis also took us through several villages throughout the island giving unique insights about historical events, traditions, and architecture. We highly recommend this agency with Antonis as your tour guide, he truly is passionate about what he does.
Review provided by Tripadvisor
Bobj345ey
Apr 9, 2026
Great tour with local and historical information - I recommend this company due to its service to clients
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Anandasinha
Apr 8, 2026
The finest way to experience Santorini - We did a private Highlights of Santorini island tour with wine tasting and had a wonderful experience. We were paired with Antonis, who did an excellent job showing us around Santorini and bringing the island’s diverse history and stories to life.
We visited during shoulder season, which meant fewer shops and eateries were open, but it also allowed us to enjoy many of the popular tourist spots almost completely empty—a huge plus. This tour is a very efficient way to see nearly all parts of Santorini in one day. Antonis began by asking about our interests and thoughtfully planned the five-hour itinerary to ensure we covered the areas that mattered most to us.
He was friendly, highly knowledgeable, and very patient, especially with our teenagers, giving them plenty of time to take photos throughout the day. His insights added great context to everything we saw.
The tour ended at Sigalas Winery, where we enjoyed a wine tasting paired with appetizers—an absolutely perfect way to conclude the afternoon. Antonis is clearly an expert in wine, and his passion and deep knowledge left us with a newfound love for Greek wines. Highly recommend this tour and Antonis as a guide.
Review provided by Tripadvisor
E1076nxangelicag
Apr 3, 2026
BEAUTIFUL TOUR - Awesome!
Our tour guide, Antonis, was amazing!
He really knows how to make a tour like this fun and enjoyable.
He was extremely knowledgable all-things Greece! :)
Review provided by Tripadvisor
K3kid
Oct 12, 2025
The best tour guide to fabulous Santorini - We had an incredibly in-depth Santorini tour, guided by George, who was fun to be with, extremely knowledgeable, with deep experience living in Greece, and skillful at navigating both busy auto traffic and pedestrian travel. He made the experience so enjoyable as he supplied answers to all our questions and prepared us for each stop including the archeological dig of the old city, the black sand beach, cities of Oia and church in the south and much more along the way. He took us to Vassaltis winery whose Santorini wines were delicious and well paired with four exceptional, ample sized dishes. I highly recommend Blue Shades of Greece tours and loved George’s guidance. Glad our concierge, Vagos, at Petite Palace recommended this tour.
Review provided by Tripadvisor
Northstar814317
Sep 20, 2025
Best day ever!!! - What a fabulous day. George was our guide and was absolutely AWESOME!
He was very informative and showed us all the sights with history and fun facts!
He has a way of drawing everyone in!
Highly recommend this tour and hope you are fortunate to have George as your guide!
Review provided by Tripadvisor
K7071btaustins
Sep 17, 2025
Excellent Tour Guide (George) and Great Tour - Our tour was absolutely spectacular! The villages especially were a highlight of the tour. George is incredibly talented, enthusiastic, genuine, and knowledgeable about the entire island, from history to local food spots. He has a great sense of humor too! Highly recommend his services! The wine tasting element gave great variety and a killer view.
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Companion65407513503
Jul 30, 2025
Excellent tour and winery visit of Santorini - We did a private island tour with wine tasting and had a wonderful time. We were paired with Adonis who did an excellent job showing us around Santorini. He took the time before we started to go over the plan for the day to make sure he covered all the areas of the island we were interested in. We appreciated his friendliness and depth of knowledge. After we had explored the island our last stop was at the winery for a tasting paired with appetizers, which was a perfect ending for our afternoon. We would highly recommend this tour with Adonis.
Review provided by Tripadvisor
Orrena2024
Jul 7, 2025
Great Tour - We highly recommend George and his team at Blue Shades of Greece. First George, whom you should ask for, was professional, thoughtful, and had a deep knowledge in the history of the Island, its topography, its many peoples throughout history, and its towns, and churches. This is a great tour for those with a genuine interest in the Island (we are a 54/48 year old couple - and did not take our five kids to Greece - it was great). In addition to the history (including leaning about the Good Friday celebrations) and sights at one of highest points on the Island, the Winery (with local wine and local cuisines was great - learned a lot about how the grapes are grown) was another highlight of the tour.
Review provided by Tripadvisor
Liannajt
Oct 10, 2025
Disappointing tour of Santorini - We were disappointed by our tour experience in Santorini. It started off well - and we enjoyed seeing some of the smaller towns that we might not have seen had we explored the island by ourselves. However, our guide's dislike for Santorini (due to too many tourists, traffic, etc) affected our overall experience of the island. When we visited Oia (one of the more popular areas) - he parked, walked 100 feet from the car and decided there were too many tourists to go anywhere else. It seemed pointless to drive there and see nothing of the area. Additionally, we understood that for the ruins we were visiting the guide could not come in with us - but he did not at all describe where we were going or what we were seeing. A main part of having a guide was to get a bit more context about what we were visiting. Lastly, we were disappointed by our visit to the winery. We have very few food specifications, but my mother cannot eat eggplant. The main course was a whole eggplant dish, leaving us with very little food for our "lunch." Overall, we so loved Santorini and it was disappointing to go on a tour, where it felt that many of the negative parts of the island were emphasized.
Review provided by Tripadvisor
