Private 5 Hours Highlights Tour by Native Guide with Wine Tasting

Navigating Santorini can be overwhelming with its endless winding streets, iconic blue-domed churches, and stunning vistas. This private 5-hour tour offers a refreshing alternative to the usual group excursions, promising a customized experience led by a local guide and including a delightful wine tasting. With the flexibility to choose your stops and a focus on authentic sights, this tour captures the true spirit of the island.

What we love most about this experience is its personalized approach—you get to set the pace and select the highlights that matter most to you, whether that’s a quiet beach, traditional villages, or panoramic views. The luxury of private transportation in a comfortable Mercedes minivan makes the day smooth and effortless, especially with hotel or port pickups included.

One thing to consider? Since this is a private tour, the cost may seem higher than group options, but the value lies in the tailored itinerary, direct interaction with your guide, and the chance to avoid the crowds. This tour works best for travelers who prefer flexibility, meaningful local insights, and a relaxed pace rather than fixed schedules.

Key Points

• Customizable itinerary allows you to focus on what interests you most on Santorini.
• Private guide and transportation enhance comfort, flexibility, and personalized attention.
• Wine tasting at Argyros Estate offers a taste of local specialties with stunning views.
• The tour is accessible for most travelers; children are welcome when accompanied by adults.
• Pickup and drop-off are included, making logistics simple.
• The tour is value-packed, considering the personalized experience and expert guidance.

A Closer Look at the Experience

This tour is designed for those who want to bypass the hectic, crowded group trips and instead enjoy a tailored, intimate experience of Santorini’s most captivating sights. The fact that it’s private means you control the itinerary and pace, which is a standout feature. You won’t be stuck rushing from one spot to another; instead, you can linger longer at places you love or skip ones that don’t appeal as much.

Transportation and Flexibility

Travel is by a luxurious Mercedes minivan, with air-conditioning to keep you comfortable even on the warmest days. The door-to-door pickup and drop-off—covering hotels, cruise ports, and the Fira cable car station—are especially convenient, saving you from navigating the island’s often confusing transport options. The driver also doubles as your guide, sharing local insights along the way.

Building Your Own Itinerary

One of the biggest advantages? You get to pick your stops. Our review mentions the flexibility to include beaches, villages, or scenic viewpoints. This means if you’re particularly interested in the famous blue domes of Fira or Oia, or want to explore less crowded villages like Pyrgos, you can incorporate that. Several reviewers appreciated the personalized route adjustment—someone with mobility concerns was grateful for fewer steps, and others loved the chance to visit their favorite spots without feeling rushed.

Exploring Santorini’s Villages

• Firostefani: Often called the “Crown of Fira,” this village offers panoramic views and a peaceful vibe. It’s a quick stop, but one that sets the scene for the beauty of the island’s northern tip.
• Imerovigli: Known as the highest town, it remains a well-preserved area with traditional Cycladic architecture—whitewashed houses and blue-domed churches. Reviewers highlight its authentic charm and breathtaking views.
• Oia: The highlight for many visitors, this village is famous for its stunning sunsets and hillside position. Our review quotes a visitor saying, “Oia is the perfect place to relax, with pastel houses and windmills descending the hillside.” It’s a must-visit, even if just for a walk and some photos.
• Pyrgos: Less touristy but equally charming, Pyrgos offers a sense of local life. The castle built around 1580 provides spectacular views of the surrounding plains and sea.

The Wine Tasting Experience

A key highlight—and a favorite among reviewers—is the stop at Argyros Estate. This modern winery is situated on the outskirts of Episkopi-Gonia, with spacious tasting rooms overlooking the vineyards. You’ll sample four different wines, gaining insight into Santorini’s unique viticulture. Reviewers appreciated the quality of the wines and the chance to relax in a scenic setting.

One guest noted that the winery visit felt different from typical tastings, thanks to the beautiful ocean views and the chance to learn about local wine production. The cost includes the tasting, making it a great value for wine enthusiasts or anyone wanting to deepen their appreciation of the island’s flavors.

Beach Stop: Kamari

The tour concludes at Kamari Beach, one of Santorini’s most popular beaches. Known for its black volcanic shingle and dramatic cliffs, it offers a different side of the island. Although walking barefoot on the pebbles can be uncomfortable under the sun, a good pair of beach shoes makes all the difference. Reviewers mention that the water is stunning, and the quieter end near Mesa Vouno is ideal for families or those seeking a more relaxed atmosphere.

How the Tour Works in Practice

Based on the reviews and the itinerary, this private tour usually lasts around 4 hours and 40 minutes to 5 hours, depending on your preferences. The timing allows for ample exploration at each stop without rushing.

Guides like Sofia, Christo, and George receive praise for their knowledge, friendliness, and flexibility. They’re attuned to personal needs—whether adjusting routes for mobility or customizing the experience based on your interests. One reviewer pointed out how their guide, Costos, even captured great photos, adding a personal touch that can make your trip memorable.

Pricing and Value

At around $231.68 per person, this tour isn’t the cheapest option, but it offers significant value. You’re paying for the personalized attention, custom route, and luxury transportation. Plus, the wine tasting and hotel/port transfers are included, which can otherwise add extra costs.

Travelers who want to see the most authentic and scenic parts of Santorini at their own pace will find this experience well worth the investment. It’s especially attractive for couples, small groups, or those celebrating a special occasion who prefer a more intimate, flexible experience.

Who Will Love This Tour?

This tour is best suited for travelers who value personalized experiences and want to avoid the rigid schedules of group excursions. It’s ideal for those who enjoy local insights, scenic drives, and tasting authentic wines. Since the itinerary is flexible, it’s perfect for people with specific interests—whether it’s charming villages, beaches, or scenic viewpoints.

It also appeals to those with mobility considerations thanks to the customizable route and private transportation. Families with older children or couples seeking a romantic, relaxed day will appreciate the comfort and intimacy this tour offers.

Final Thoughts

This private tour offers an excellent balance of sightseeing, flexibility, and culture. The expert guides genuinely enhance the experience with their local knowledge, and the custom itinerary ensures you get exactly what you want out of your few hours on Santorini. The inclusion of wine tasting at Argyros Estate adds an extra layer of enjoyment, making it a well-rounded day.

While the price might be higher than shared tours, the value in personalized service and comfort makes it a worthwhile investment if you seek a relaxed, authentic way to explore the island. It’s especially suited for those who want to craft a memorable, tailored experience with plenty of room for spontaneous stops and local insights.

Who is this tour suitable for?
This private tour is ideal for travelers who want flexibility and personalized attention. It suits couples, small groups, or families with older children who appreciate comfort, scenic stops, and local insights.

What does the tour include?
It features private transportation in a Mercedes minivan, hotel or port pickup and drop-off, a guided itinerary, wine tasting at Argyros Estate, bottled water, and a private guide.

Are there any hidden costs?
The tour price covers all listed features, including the wine tasting. Lunch and additional alcoholic beverages are not included and are at your discretion.

Can I customize the stops?
Yes, the tour is designed to be flexible. You can select from beaches, villages, or scenic viewpoints, and your guide will help tailor the route.

How long does the tour last?
Expect about 4 hours and 40 minutes to 5 hours, depending on your preferences and the stops included.

Is this suitable for cruise ship passengers?
Yes, pickup and drop-off at the Fira cable car station are included, making it convenient for cruise travelers.

What about accessibility?
The tour can be adjusted for those with mobility concerns, and the private nature allows for route modifications to minimize walking.

How many wines will I taste?
You will sample four different glasses of local wine at Argyros Estate, offering a nice variety to enjoy.

What if the weather is bad?
If canceled due to poor weather, you’ll be offered a different date or a full refund. The experience requires good weather to fully enjoy the outdoor stops.

This private, flexible, and culturally rich tour offers a well-rounded way to experience Santorini beyond the usual crowds. Whether you’re after stunning vistas, authentic villages, or a taste of local wine, it’s a memorable way to discover the island’s true essence.