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Experience Santorini’s highlights on a private tour with wine tasting, stunning sunset views in Oia, and visits to historic villages and a monastery, all in 5 hours.
Discover Santorini’s Charm with a Luxury Sunset Tour
Santorini is undeniably one of the world’s most enchanting islands, famous for its breathtaking sunsets, whitewashed buildings, and volcanic landscapes. This 5-hour private tour offers a taste of the island’s most iconic sights, paired with opportunities to indulge in local wines and enjoy a sunset in Oia without the crowds. Whether you’re celebrating a special occasion or simply craving a curated experience, this tour promises a blend of culture, scenic beauty, and personalized service.
What we love most about this experience is how seamless and intimate it feels — a private tour with a knowledgeable guide, flexible stops, and a carefully curated itinerary that highlights Santorini’s authentic charm. The inclusion of wine tasting at Greece’s only underground wine museum really elevates the experience, adding a delicious local twist.
One potential consideration is the price — at around $324 per person, it’s a significant investment, but the personalized nature and inclusion of meals, transportation, and entry fees help justify the cost. This tour suits travelers who appreciate comfort, exclusive access, and a deep dive into Santorini’s culture, all while enjoying the island’s most stunning vistas.


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The adventure begins at the Museum of Prehistoric Thera in Fira at 3:00 pm. From here, you’ll be whisked away by an air-conditioned minivan, setting the tone for a comfortable and relaxed journey. The timing is ideal to experience the island’s highlights while avoiding the midday heat and crowds. Since it’s a private experience, your guide can tailor the pace, allowing for spontaneous photo stops or additional explanations.
Your first stop is Megalochori, a village that seems to have leapt right out of a postcard. As you stroll through its narrow, winding streets, you’ll notice the preservation of traditional architecture and the peaceful atmosphere that sets it apart from busier parts of the island. The guide, likely a local with storytelling flair, will explain the village’s history, making the 30-minute walk both informative and visually delightful.
Reviewers have praised guides like Maria, noting their friendliness and knowledge, which enhances the authenticity of this visit. One reviewer described the dinner in Oia as “delicious with a magnificent view and sunset,” emphasizing how the small details — like a well-chosen guide — can turn a good tour into a memorable one.
Next, you’ll venture underground to the Wine Museum — an 8-metre-deep labyrinth shaped to showcase the history of Santorini’s wines since 1660. This 45-minute stop is a highlight for wine lovers and curious travelers alike. The labyrinthine tunnels stretch for 300 metres and provide an immersive experience into the island’s viticultural past, with depictions and displays that tell stories of local winemaking traditions.
The tour includes a wine tasting of four select wines, in a cozy, specially designed space that accentuates the volcanic notes of the wines. This isn’t just a quick sip — it’s a chance to appreciate the distinct character of Santorini’s volcanic terroir, which is often a point of praise from visitors. The fact that the guide makes the experience engaging and informative makes this stop both educational and delicious.
After wine, your journey continues to the Prophet Elias Monastery, perched high on a hilltop. This spot offers sweeping panoramic views of the island, making it a perfect place for photos and a breather from the day’s sightseeing. The 20-minute visit is brief but impactful, offering insight into local religious traditions and providing photo opportunities that capture Santorini’s volcanic landscape.
Evening activities in Santorini include these interesting options
The finale is a 2-hour visit to the village of Oia, renowned for its mesmerizing sunsets. Unlike the crowded evenings often associated with Oia, this tour ensures you experience the sunset in a more exclusive, peaceful setting. You’ll wander the charming alleys lined with whitewashed houses, vibrant accents of ochre, fuchsia, and cobalt, and enjoy a traditional Cycladic dinner overlooking the Aegean Sea.
Reviewers echo how special this part of the tour is. One mentioned, “the dinner was delicious with a magnificent view and sunset,” highlighting how the experience combines visual beauty with local cuisine. The guide’s local insight helps you find the perfect vantage point, away from the throngs of travelers, making it a truly serene and picture-perfect moment.

This tour’s inclusions — dinner, all fees and taxes, mineral water, transportation, pickup/drop-off, and wine tasting — offer a comprehensive package for the price. The fact that all admission fees are covered means no hidden costs, and the private nature of the experience ensures a personalized touch.
The convenience of hotel pickup and drop-off in a comfortable vehicle means you don’t have to worry about navigating or parking, especially in popular spots like Oia. Plus, the small-group or private setting maximizes flexibility, allowing your guide to adapt the itinerary if you want more time at certain stops or to explore additional areas.
At $323.91 per person, this isn’t the cheapest way to see Santorini, but considering the personalized service, curated stops, and inclusions like wine and dinner, it’s a good value for travelers seeking a seamless, high-end experience. Many travelers appreciate the attention to detail and the opportunity to enjoy the island without the hassle of planning each stop.

This experience suits travelers who want a luxurious, hassle-free day exploring Santorini’s highlights with a private guide. It’s perfect for couples, honeymooners, or small groups celebrating a special occasion. If you’re a wine enthusiast or photography lover, the stops at the underground winery and Oia’s sunset will particularly appeal.
While it’s on the higher end of the price spectrum, the inclusions and personalized nature make it a worthwhile splurge if you value comfort, exclusivity, and authentic insights. It’s especially great for those pressed for time but eager to capture the essence of Santorini in a single, well-curated half-day.

This private tour offers a well-balanced mix of culture, scenery, and culinary delights, all set within a manageable 5-hour window. The thoughtful itinerary, combined with the personal attention from guides, ensures you experience Santorini in a way that feels both special and authentic. From the quiet charm of Megalochori to the volcanic wines and spectacular sunset, every element has been chosen to give you a genuine taste of the island’s magic.
If you’re after a relaxed, intimate experience that showcases Santorini’s most iconic sights without the crowds, this tour hits the mark. It’s especially suited for travelers who value flexibility, comfort, and a touch of luxury in their vacation.
On the other hand, if you’re on a strict budget or prefer self-guided exploration, you might find this experience a bit pricey. But for those looking to indulge in a seamless, memorable day with expert insights and breathtaking views, this tour delivers on every front.
Is hotel pickup available for this tour?
Yes, pickup and drop-off are included from designated meeting points and all hotels or villas in Santorini, making the experience very convenient.
How long does the tour last?
The tour lasts approximately 5 hours, starting at 3:00 pm and ending back at the meeting point.
Are all fees included in the price?
Yes, all fees and taxes are included, along with mineral water, wine tastings, and dinner, ensuring no hidden costs.
Can I cancel the tour if my plans change?
Yes, free cancellation is available up to 24 hours before the scheduled start, with a full refund.
What should I wear or bring?
Comfortable shoes are recommended for walking, especially in villages and at the monastery. Don’t forget your camera for those spectacular views.
Is the tour suitable for children or elderly?
Most travelers can participate, but consider mobility — the tour involves walking and some uneven terrain, especially at the villages and monastery.
What makes this tour special compared to others?
The personalized, private experience combined with a curated itinerary, wine tasting in Greece’s only underground wine museum, and a serene sunset in Oia sets this tour apart.
This carefully curated experience promises a blend of Santorini’s best sights, tastes, and views, all delivered with a touch of luxury and local charm. Whether you’re celebrating a honeymoon or simply want a memorable way to explore the island, it offers a taste of Santorini’s magic with none of the hassle.