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Discover Santorini’s highlights on a luxury tour featuring scenic stops, local wine tasting, and a sunset in Oia, topped with a delicious dinner.
Exploring Santorini with the Luxurious Highlights Tour and Dinner
If you’re looking to experience the best of Santorini in a day, this Luxurious Highlights Tour with Dinner offers a balanced blend of sightseeing, cultural insight, and relaxing indulgence. Priced at around $329 per person, it’s a more premium option, but one that promises a carefully curated adventure with a focus on comfort and authentic experiences. Traveling by a luxury, air-conditioned minivan with an expert guide, you’ll get to see some of the island’s most iconic sights, taste local wines, and unwind in the picture-perfect setting of Oia at sunset.
What really appeals to us about this tour is the thoughtful itinerary that combines scenic viewpoints, cultural spots, and leisurely activities. The inclusion of local wine tasting and a dinner in Oia elevates it beyond typical sightseeing, turning it into a full-day indulgence. A potential consideration is the 5-hour duration—if you’re strapped for time or prefer a more flexible pace, this might feel a bit structured. However, for anyone wanting a comprehensive, well-organized experience that hits all the highlights, it’s a fantastic fit. This tour is particularly suited to travelers who value comfort, expert guidance, and a taste of luxury amidst stunning natural beauty.


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The tour kicks off in Megalochori, a village that exudes charm with its traditional aesthetics and peaceful ambiance. It’s a quieter spot compared to the crowds of Fira or Oia, giving you a taste of authentic local life. Walking through narrow cobblestone streets, you might notice how the architecture blends harmoniously with the volcanic landscape, and it’s a fantastic place for photos. The review mentions this as one of the “most serene and beautiful gems,” making it the perfect peaceful start before the busy day.
Next, the group heads to Prophet Elias Monastery, perched atop the highest point of the island. The short visit offers sweeping 360-degree views of Santorini, ideal for snapping pictures and appreciating the island’s volcanic geography. The guide’s commentary—likely provided by someone like Panos, known for local insights—adds context to this spiritual site. Expect around 20 minutes here, a good short stop that balances sightseeing with scenic photo ops.
Perhaps the most renowned part of the day is the sunset in Oia, lasting around two hours. This is where you’ll witness the famous white houses and colorful domes carved into volcanic rock, all bathed in the golden glow of sunset. Oia has long inspired painters and poets, and you’ll understand why as you watch the sky change colors over the caldera. The review highlights this as unsurpassed in beauty, making it a highlight worth the price.
A visit to the Wine Museum Koutsogiannopoulos is a unique experience—it’s Greece’s only underground wine museum, carved 8 meters below ground. The labyrinth-like 300-meter stretch offers an immersive walk through the island’s wine history and viniculture. The review points out that locals love the variety of local wines, and the museum’s setting provides a fascinating contrast to the above-ground scenery. Expect about 40 minutes here, enough to taste and learn without rushing.
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The tour wraps up with a dinner in Oia, which offers a chance to relax and savor authentic Greek cuisine. While the specifics of the meal aren’t detailed, the inclusion of dinner adds value—an opportunity to unwind after a full day of sightseeing, with the bonus of eating in one of the most famous spots on the island.

The tour provides transport in a luxury minivan, which is a significant advantage for comfort—no cramped bus or long walks between stops. Pickup and drop-off ensure a seamless experience, especially if you’re staying in a central area. The wine tasting adds a cultural and sensory dimension, allowing you to sample local varieties that you might not find elsewhere. Plus, all fees and taxes are covered, so no hidden costs.
The dinner in Oia is a standout feature, giving you an authentic, relaxed dining experience with local flavors. Plus, mineral water is provided, helping you stay refreshed throughout the day.

While the price tag might seem steep at over $300 per person, considering everything included—transport, guided tours, wine tasting, and dinner—it’s arguably a well-rounded deal. The emphasis on comfort and quality makes it particularly appealing for travelers who prefer a more curated experience rather than self-guided wandering.
The guide, Panos, has received praise for his expertise and local knowledge, which can make a difference in appreciating the island’s stories and hidden details. One reviewer even highlighted the dinner as “unique”, indicating the meal’s quality and authenticity.
This tour is ideal for travelers who value comfort, expert guidance, and a thoughtfully curated itinerary. It suits those who want to see key sights without the hassle of planning, plus enjoy local wine and a scenic sunset. It’s perfect if you’re looking for a luxury experience that combines sightseeing with culture and culinary delights.
However, if you prefer a more flexible schedule or are on a tighter budget, you might want to consider other options. Still, for those who want a well-organized, memorable day in Santorini that hits all the highlights, this tour offers great value.

What is the duration of the tour?
It lasts about 5 hours, making it a half-day experience that’s packed but not rushed.
Is pickup included?
Yes, pickup and drop-off are offered, making the experience convenient from most locations.
What should I wear?
Comfortable clothing suitable for walking and sightseeing is best, plus a hat and sunscreen for sun protection.
Is the tour suitable for all ages?
Most travelers can participate, but it’s best suited for those comfortable with walking and a structured schedule.
Are meals included?
Yes, the tour includes a dinner in Oia, giving you a chance to enjoy local dishes in a stunning setting.
Can I cancel if my plans change?
Yes, there’s free cancellation up to 24 hours before the tour, with a full refund.
What is the wine tasting about?
You’ll sample local wines at the underground Wine Museum, which features a historical and sensory journey through Santorini’s viticulture.
How many people typically join the tour?
It’s a private tour, so only your group participates, ensuring personalized attention.
Is the tour wheelchair accessible?
While not explicitly stated, most stops involve walking on cobblestone streets, so mobility considerations may apply.
What makes this tour stand out?
The combination of luxurious transport, expert guidance, cultural stops, wine tasting, and sunset in Oia makes it a comprehensive and memorable way to experience Santorini.
To sum it up, the Santorini Luxurious Highlights Tour with Dinner offers a well-rounded, comfort-focused way to see the island’s most iconic sights. It is especially suited for those who appreciate guided experiences, cultural insights, and a touch of luxury. With stunning views, knowledgeable guides, and a chance to taste local wines and enjoy a scenic sunset, it promises a memorable day that captures the essence of Santorini’s charm. If you’re looking for a curated, premium experience that balances sightseeing, relaxation, and authentic flavors, this tour is definitely worth considering.