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Experience Santorini's highlights in 5 hours with luxury transport, wine tasting, a scenic village walk, monastery visit, and a sunset in Oia, ending with dinner.
Santorini Luxurious Highlights Tour with Dinner offers an elegant way to explore this iconic island in about 5 hours. Priced at $329.26 per person, the tour combines comfort, culture, and breathtaking scenery. Traveling in a luxury, air-conditioned minivan, guests enjoy insightful commentary from an expert guide, along with visits to charming villages, historic sites, and a famous sunset spot. The tour culminates with a delicious dinner at Oia, complemented by a local wine tasting and free time to marvel at the sunset views. While the experience is well-paced and tailored for those seeking a rundown, it’s best suited for visitors who appreciate a mix of sightseeing, cultural insights, and scenic relaxation.
This tour stands out with its inclusion of a wine museum, a scenic village walk, and a monastery visit—plus, the convenience of pickup and drop-off. Only group discounts are available, and the tour is designed for most travelers, with flexible cancellation policies. Although the itinerary is rich with highlights, it’s a shorter experience, ideal for those who want a luxurious overview without overextending their day.


The tour begins with the convenience of pickup and drop-off from designated locations, making logistics straightforward. Traveling in a luxury, air-conditioned minivan, guests experience a comfortable ride while the guide shares stories and facts about Santorini’s culture and history. This focus on comfort and personalized service enhances the overall experience, especially after a day of exploring the island’s highlights.
The group size is designed for intimacy, and group discounts may be available, offering good value for those traveling with family or friends. The mobile ticket option adds flexibility, and all fees and taxes are included in the price of $329.26.
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The tour’s first stop is Megalochori, a village celebrated for its peaceful ambiance and distinct aesthetic. Visitors walk through its narrow streets, discovering whitewashed houses and colorful details that showcase authentic local architecture. The 30-minute walking tour provides a gentle introduction to the island’s rural charm, with plenty of opportunities for photos and quiet contemplation.
Because admission is free, this stop offers a taste of traditional life without added costs. The tranquil atmosphere makes it a perfect start to the day, capturing the essence of Santorini’s quiet beauty away from busier tourist spots.

Next, the Prophet Elias Monastery sits atop the highest point on the island, offering spectacular panoramic views of Santorini. The 20-minute stop allows visitors to take in the scenery and snap photos from the hilltop location. The monastery itself adds a sense of tranquility and spiritual significance, making it a meaningful sight on the itinerary.
Since admission is free, this stop emphasizes natural beauty and historical architecture, giving guests a peaceful pause while soaking in the vast vistas of the island, caldera, and the blue Aegean Sea.

The tour’s highlight is spending about 2 hours in Oia, renowned worldwide for its breathtaking sunset. The village’s iconic white houses, carved into volcanic rock, spill down toward the sea, creating picture-perfect scenery. Visitors have free time to explore at their own pace, shop for souvenirs, or simply relax while waiting for sunset.
The included sunset views are a major draw, with Oia’s charming streets providing countless opportunities for stunning photographs. The dinner at Oia is scheduled after sunset, offering a chance to enjoy local cuisine while immersed in the village’s magical atmosphere.

A visit to the Wine Museum Koutsogiannopoulos presents a fascinating insight into Santorini’s viniculture. As the only underground wine museum in Greece, it stretches 300 meters in a labyrinthine space 8 meters below ground. The museum showcases the history of wine-making and daily life of local vine growers through engaging exhibits.
This 40-minute stop enriches the tour with cultural depth, offering a chance to learn about the island’s wine heritage. It’s a standout feature that combines education with a unique underground setting, making it memorable for wine lovers and curious travelers alike.
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The tour concludes with a dinner at Oia, providing a relaxing end to the day. The included dinner offers a taste of local flavors, rounding out the experience with authentic cuisine. This meal, paired with local wines during the tasting, allows guests to unwind while enjoying Oia’s scenic ambiance.
The combination of dinner and wine tasting ensures that the day ends on a flavorful note, with ample time for reflection and enjoying the stunning sunset backdrop.
Designed for comfort and culture, this tour balances sightseeing, tasting, and relaxation. The pace is manageable, with enough time at each stop to appreciate the sights without feeling rushed. The shorter duration makes it suitable for visitors who want a rundown without a full day commitment.
While the itinerary is packed, it remains accessible for most travelers, including those with moderate mobility. The tour’s small group setting fosters a personalized experience, with the expert guide sharing insights and answering questions along the way.

This luxury highlights tour appeals most to visitors seeking an upscale, curated experience. It is ideal for those interested in cultural sites, scenic views, and wine tasting, all in a comfortable setting. The dinner at Oia adds a romantic or relaxed touch, perfect for couples or small groups.
Because it offers less walking than some full-day tours, it suits travelers who prefer a leisurely pace. The inclusion of key sights like Megalochori, Prophet Elias Monastery, and Oia’s sunset makes it a well-rounded introduction to Santorini’s most beloved spots.
The Santorini Luxurious Highlights Tour with Dinner delivers a rich yet relaxed overview of the island’s best features. The luxury transport, expert guide, and well-chosen stops elevate the experience beyond standard sightseeing. Guests appreciate the blend of scenic views, cultural insights, and the chance to indulge in local wine and cuisine.
While the experience is shorter than full-day tours, the quality of stops and the comfort offered make it a compelling choice for those wanting a luxurious introduction to Santorini. It suits travelers who prefer a personalized, culturally rich outing over more extensive tours, especially those eager to enjoy Oia’s sunset and local flavors.
“Perfect tour! Panos is expert guide. He gave us special informations about the island as a local !!also the diner was unique!!”
Is the tour suitable for all ages?
Yes, most travelers can participate, as the tour is designed for a broad audience with moderate walking.
What is included in the tour price?
The tour includes transportation, guided visits, wine tasting, dinner at Oia, all fees and taxes, and free cancellation if needed.
How long does each stop last?
The Megalochori village stop lasts about 30 minutes, the monastery about 20 minutes, the wine museum for 40 minutes, and Oia has around 2 hours for exploring and sunset viewing.
Is the wine tasting part of the experience?
Yes, the tour features local wine tasting as part of the itinerary, enhancing the cultural experience.
Can I cancel the tour?
Yes, cancellations are free up to 24 hours before the scheduled start, with full refunds available.
Does the tour cater to dietary restrictions?
The provided information does not specify dietary accommodations; it’s best to inquire directly with Pigaia travel for special requests.
Is transportation comfortable?
Absolutely, traveling in a luxury, air-conditioned minivan ensures a comfortable ride.
Are the stops accessible for mobility-impaired travelers?
While not explicitly detailed, the stops are generally accessible, but it’s advisable to check with the provider for specific needs.
What makes this tour stand out?
The combination of scenic village walks, panoramic monastery views, underground wine museum, and sunset in Oia, all with luxury transport and dinner, offers a well-rounded, upscale experience.
Would this tour be good for a romantic getaway?
Definitely, with sunset views, dinner, and a peaceful vibe, it suits couples seeking a memorable, relaxed evening.