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Discover Santorini’s Venetian castles, charming villages, and stunning sunset in Oia on this small-group, full-day tour with wine tasting and cultural insights.
Explore the captivating beauty of Santorini with this 8-hour small-group tour priced at $102 per person. Led by an engaging guide, the tour takes you through some of the island’s most iconic Venetian castles, charming villages, and scenic spots, all in a comfortable air-conditioned vehicle. With a maximum group size of 18 people, this experience promises a personalized and immersive day, perfect for those eager to see diverse highlights without feeling rushed.
From exploring Pyrgos, built on a hilltop, to relaxing at the volcanic black sand beach at Perivolos, every stop offers unique views and stories. The tour concludes with the spectacular sunset in Oia, a highlight that many reviews praise for its breathtaking scenery. The inclusion of wine tasting and an interactive music show adds cultural depth, making this tour ideal for travelers wanting a well-rounded day of discovery.
Despite the full itinerary, the pace remains manageable thanks to transportation in a comfortable, air-conditioned minivan. This tour is best suited for those comfortable with walking moderate distances and eager to learn about Santorini’s history and local culture. Note that entrance to the Symposion costs 13 EUR and is optional, and that the tour does not include meals or drinks beyond wine tasting.


The tour begins with a pickup from your hotel in Thera, setting the stage for a carefully curated day. The first stop is the picturesque village of Pyrgos, perched on a hilltop, where you walk to the Venetian castle that overlooks the caldera. This spot offers sweeping panoramic views of the island, making it a favorite for photos and leisurely exploration.
Next, the guide leads you through Megalochori, a traditional village famous for its charm and the Symposion, a workshop of Greek music instruments. This visit combines music, mythology, and local traditions, providing insight into Greece’s cultural heritage. The interactive music show is a highlight praised for its engaging presentation and storytelling.
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After the cultural visit, the group drives around Akrotiri, one of the island’s most famous archaeological sites. A brief photo stop here offers stunning views of the caldera from the south side of the island. The guide points out the castle of Akrotiri and shares stories about its historical significance.
Following this, you’ll have free time at Perivolos Beach, renowned for its volcanic black sand. This relaxing break lasts about 1.5 hours, giving plenty of opportunity to swim, sunbathe, or enjoy lunch tasting local flavors. Many find this spot a perfect way to unwind amid Santorini’s natural beauty.

The next stop is Emporio, a charming village full of narrow streets and traditional architecture. Here, you visit the best-preserved Venetian castle, once a key trade center during medieval times. The site is walkable and offers a glimpse into Santorini’s historical strategic importance.
After exploring, the group relaxes in an old winery where local wines are sampled. This tasting experience is often praised for its authenticity and the chance to try regional varieties in a historic setting.

The tour then makes a short stop in Firostefani, where travelers capture spectacular photos of the famous Blue Dome church. From this vantage point, the outstanding views of the caldera are a favorite among visitors. The guide shares stories about the area’s religious and historical significance.
The Rock of Skaros, once the capital during Venetian rule, is another scenic highlight. Though only a brief visit, the views from this spot are notable and perfect for photos.
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The final destination is Oia, with ample time to wander through its narrow passageways and cave houses. The charming captain’s houses and romantic chapels add to the village’s allure. Many reviews mention how lively yet photogenic Oia remains, even during busy sunset hours.
The sunset in Oia is the tour’s climax, with many visitors appreciating the chance to watch the caldera glow from inside the Venetian castle. This moment offers perfect photo opportunities and a memorable end to the day.

The tour provides hotel pickup and drop-off in Thera, with transportation via air-conditioned minivan. The schedule involves several short drives between stops, with most activities including guided walks and free time to explore. The group size of up to 18 ensures a comfortable and intimate experience, with plenty of opportunities to ask questions.
The tour includes wine tasting at a local winery and an interactive music workshop, both of which are highly appreciated. Entrance to the Symposion costs 13 EUR and is optional, so travelers can choose whether to participate in that specific activity.

This tour suits history and culture enthusiasts eager to learn about Santorini’s past, with knowledgeable guides sharing stories and insights. The small-group setting makes it ideal for those who prefer a more personal and relaxed pace. Active travelers who don’t mind walking moderate distances will enjoy the exploration of villages and scenic viewpoints.
Those interested in local wine and music traditions will find the included tastings and workshop enriching. However, travelers with mobility issues or low fitness levels should consider the walking involved, particularly at the Venetian castles and village explorations.

At $102 per person, this tour delivers a rundown of Santorini’s most iconic sites with the benefit of expert narration. The small-group format enhances your experience by allowing more interaction and personalized attention. Many reviews emphasize the knowledgeable guides, especially mentioning Gregory for his storytelling and local insights.
The combination of cultural stops, scenic views, and relaxing breaks creates a balanced itinerary. The sunset in Oia remains a favorite moment, made more special with transportation included, avoiding long waits or busy public transport. This tour offers good value for travelers looking to see a lot of Santorini without the hassle of organizing separate visits.

This 8-hour journey provides a well-rounded look at Santorini’s history, culture, and natural beauty. The focus on Venetian castles, traditional villages, scenic viewpoints, and local wine tasting makes it a rich experience. The small group size and personalized guide service are definite strengths, ensuring you get attention and stories behind each site.
While the tour involves walking some distance and does not include meals, the spectacular sunset and cultural insights compensate for these minor considerations. It’s a strong choice for travelers seeking a comprehensive, engaging day that showcases Santorini’s most beloved features.
“Gregory was a fantastic guide. With his local history and culture knowledge, he made our tour fun. If you have limited time then this tour covers m…”
What is the duration of this tour?
The tour lasts 8 hours, with departure times based on availability.
What is included in the tour price?
The price includes hotel pickup and drop-off, transportation in an air-conditioned minivan, wine tasting, and a tour escort.
Are entrance fees included?
The entrance fee to the Symposion is 13 EUR and is optional. Other site entrances are included in the tour.
Is this tour suitable for children?
The tour is not suitable for children under 3 years or people with mobility impairments, and not recommended for pregnant women or those with heart problems.
Can I cancel the tour?
Yes, full cancellation is available up to 24 hours in advance for a full refund.
What should I bring?
Bring comfortable shoes for walking and swimwear for beach breaks.
Is the sunset guaranteed?
Sunset viewing depends on weather conditions; clear skies enhance the experience, but cloudy weather may limit visibility.
How many people are in the group?
The group maximum is 18 guests, ensuring a more intimate and personalized experience.
Can I book this tour last-minute?
Yes, you can reserve now and pay later with flexible booking options, subject to availability.
What makes this tour different from others?
The small-group format, comprehensive itinerary, and local guide expertise — especially Gregory’s storytelling — set this tour apart.