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Discover Santorini's highlights on a private 5-hour tour including iconic sites, stunning viewpoints, and a wine tasting at a unique local winery.
Exploring Santorini with the Private Highlights Tour & Wine Tasting offers a rich and personalized way to see the island. For $178.22 per person, this approximately 5-hour experience is led by knowledgeable local guides who prioritize your comfort and insights. The tour includes private transportation, air-conditioned vehicles, and stops at some of the most photogenic and historically significant sites, complemented by a wine tasting of four local wines at a distinctive winery.
Designed for those seeking a deeper connection with Santorini beyond quick snapshots, this tour is especially appealing to visitors who value history, culture, and authentic experiences. While it covers many of the island’s highlights in a short time, it’s best suited for travelers with a moderate level of mobility because of the walking involved at some stops.


The tour begins with visits to Red Beach and Perissa Black Sand Beach, two of Santorini’s most famous shoreline spots. Red Beach is renowned for its striking red volcanic sand, formed from pulverized volcanic rock from the nearby caldera. This beach is a popular photo spot, though some areas have been inaccessible since 2013 due to landslides. Expect around 25 minutes here, with free entry.
Next, the group heads to Perissa Beach, the longest sandy stretch on the island. Its crystal-clear waters make it perfect for a quick photo or a moment of relaxation. The site also features the remnants of an Early Christian church of Saint Irene, adding a touch of historical intrigue. Here, visitors spend about 30 minutes and enjoy free access.
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A key highlight is the visit to Prophet Elias Monastery, situated at approximately 567 meters above sea level atop Mount Profitis Ilias. The monastery, the highest point on the island, offers stunning views of Santorini’s landscape and sea. The stop lasts about 20 minutes, giving ample time to capture photos and absorb the scenery, all without an admission fee.
This site provides an ideal spot for those wanting to see Santorini from above and appreciate the island’s volcanic terrain. The guides often share insights into local religious traditions, adding depth to the experience.

The village of Pyrgos Kallistis is a well-preserved example of medieval architecture. Built amphitheatrically on a hill, Pyrgos features narrow, labyrinthine streets, fortified walls, and the remains of a Venetian castle known as Kasteli. This stop lasts about 45 minutes and is free to explore.
Visitors can enjoy sweeping views of the island from its elevated position. Pyrgos remains one of the least touristy villages, offering a more authentic feel of traditional Greek life and architecture, making it a peaceful contrast to the busier towns.

A standout part of this tour is the wine tasting at Art Space Winery, housed in an 1861 old winery carved from pumice rock. The winery hosts a museum of contemporary Greek art, displaying works of painting and sculpture, giving visitors a chance to connect with Greece’s artistic side.
The wine tasting includes four local wines, with a focus on unique, high-quality products. The winery also maintains a traditional winemaking process, which guests find particularly interesting. The visit here lasts 1 hour 15 minutes, providing enough time to savor wines and explore the art exhibits.

The Three Bells of Fira is a well-known church with a distinctive blue dome and three bells. Located above the cliffs of Fira, this site offers stunning views of the caldera and picturesque surroundings. The stop lasts around 15 minutes and is free to visit.
Photographers appreciate this location for capturing classic Santorini imagery, but it can be crowded. Guides often recommend the best angles or less busy times for photos.
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The tour culminates at Oia, famous for its white-painted houses, blue domes, and narrow alleys along the volcanic crater’s edge. Built into the hillside, Oia’s architecture reflects the traditional Cycladic style. Visitors spend about 45 minutes exploring its streets, enjoying views, and capturing pictures.
Oia is also known for neo-classical mansions built by wealthy ship captains in the 19th century. The town’s preservation efforts since 1976 ensure that its charm remains intact, making it a highlight for photography and casual wandering.

This private tour offers pickup service, making the start seamless. The transportation is air-conditioned, ensuring comfort during the approximately 5-hour itinerary. Bottled water is provided, and the wine tasting at the Art Space Winery is included, featuring 4 local wines for guests over 18.
Since it’s a private activity, only your group participates, allowing for a flexible and personalized experience. The tour operates with group discounts available and uses a mobile ticket for convenience.

This tour is ideal for first-time visitors who want a rundown of Santorini’s most famous spots while enjoying personalized attention. The experienced local guides are praised for their friendliness and in-depth knowledge, making the journey both informative and enjoyable.
It suits travelers looking for a balanced mix of sightseeing, culture, and wine tasting. Because the stops involve some walking and sightseeing, it’s best for those with moderate mobility. The 5-hour duration fits well into a day’s exploration, especially for cruise guests or short-stay visitors.
By combining scenic viewpoints, historic villages, beautiful beaches, and a wine tasting, this tour offers a well-rounded encounter with Santorini’s charm. The private format guarantees a tailored experience, with guides who are often praised for their extensive knowledge and friendly approach.
Most importantly, the 5-star rating from 33 reviews indicates high satisfaction, especially noting the quality of the guides, the diversity of sites, and the value for money. For those eager to see Santorini’s highlights in a manageable, enjoyable package, this tour provides a practical, personable way to experience the island’s best.
“The island of Santorini is beautiful but if you don't know your way around, are you really miss it's true beauty. Elias promptly picked us up in a …”
What’s included in this tour?
The tour includes private transportation, bottled water, and a wine tasting of 4 local wines at the Art Space Winery. Pickup is offered, and the vehicle is air-conditioned.
How long does the tour last?
It lasts approximately 5 hours, making it perfect for a short visit or cruise day.
Can I customize the stops?
As a private tour, the itinerary is flexible, and guides are happy to accommodate specific interests or needs within the duration.
Are there any costs at the stops?
Most stops, including beaches, Pyrgos, the Three Bells church, and Oia, are free to visit. The wine tasting is included in the price.
Is this tour suitable for children or elderly?
The tour involves some walking, especially in Pyrgos and Oia. It’s best suited for those with moderate mobility.
What is the guide’s role during the tour?
Guides are knowledgeable locals who explain the history and culture of each site, answer questions freely, and help capture memorable photos.
What is the price per person?
The cost is $178.22, which includes all activities and transportation.
Do I need to book in advance?
Yes, this tour is often booked about 85 days in advance and offers free cancellation up to 24 hours beforehand.
Is alcohol served during the tour?
Yes, the wine tasting features four local wines, exclusively for guests over 18.
Can service animals participate?
Yes, service animals are allowed on this private tour.
Will I get good photo opportunities?
Absolutely. Guides often assist with photos at key locations like Oia and the Blue Dome Church. They know less crowded spots for better pictures.
How do I book this tour?
You can reserve through platforms like Viator, where it’s recommended for its ease and flexibility.