Private 5 Hours Highlights Tour by Native Guide with Wine Tasting

When it comes to experiencing Santorini, many travelers are familiar with the crowded cruise ship excursions or large bus tours. But if you’re after a more intimate, flexible, and authentic way to enjoy the island’s highlights, this private 5-hour tour managed by Top Santorini Tours offers a refreshing alternative. It’s designed for those who want to shape their own adventure, guided by a local who knows the ins and outs of this volcanic wonder.

What makes this experience stand out? First, the customizable itinerary gives you the freedom to choose your favorite spots—whether that’s sandy beaches, picture-perfect villages, or scenic overlooks. Second, the wine tasting at Argyros Estate adds a flavorful local touch that many visitors miss in larger tours. However, it’s worth noting that the price point might seem high for some, but considering the private nature and personalized approach, it’s a worthwhile investment for those seeking quality over quantity.

This tour is ideal for travelers craving a tailored experience, those who prefer avoiding large groups, or anyone who wants to explore at their own pace without feeling rushed. It’s especially good if you’re staying in multiple locations or arriving via cruise, as pickup is available from most hotels, ports, and even the Fira cable car station.

Key Points

• Personalized Experience: Build your own itinerary with a local guide, focusing on what interests you most.
• Comfort and Convenience: Door-to-door service with private transport ensures a smooth day.
• Authentic Santorini Vibes: Visit traditional villages and scenic spots away from the crowds.
• Wine Tasting: Savor four different wines at the well-loved Argyros Estate, with a chance to learn about local varieties.
• Flexible Timing: The tour lasts just under five hours, giving you ample time to explore without feeling hurried.
• Ideal for Private Groups: Only your party participates, making it perfect for couples, families, or friends.

A Detailed Look at the Tour Itself

This tour is all about flexibility and quality. Unlike typical bus excursions, it offers a chance to customize your route in collaboration with your guide. We love the way this approach respects your pace and interests, whether that’s wandering through ancient villages or relaxing on a beach.

The tour kicks off with a visit to Firostefani, often called the “Crown of Fira,” perched at the highest point of the main town. It’s a quiet, less crowded spot with sweeping views, perfect for snapping photos or simply soaking in the scenery. The fact that it’s free of charge makes it a great starting point, allowing travelers to enjoy a peaceful moment before heading to busier areas.

Next, the guide takes you to Imerovigli, the highest town in Santorini. Here, you’ll find white houses and blue-domed churches that epitomize Cycladic charm. The preserved architecture gives you a real sense of local life, and although it attracts plenty of visitors today, the town still retains a traditional feel. One reviewer noted how their guide helped them avoid too many steps due to a medical condition—showing the tour’s flexibility.

A highlight of any trip to Santorini is a stop in Oia, renowned worldwide for its spectacular sunsets. While most visitors come for the view, you’ll get an authentic experience during your visit—no crowds needed, as the tour allows for a relaxed exploration of the hillside houses, windmills, and charming alleys. The one-hour visit might seem brief but is enough to soak in the magic and snap countless photos. Many reviews praise guides who shared local stories and photography tips, making this stop more than just a postcard scene.

The tour continues to Pyrgos, a traditional village crowned by its 1580 castle. Walking through Pyrgos, you’ll feel like a local, with narrow lanes and atmospheric views of plains and the sea. The 30-minute stop offers a chance to breathe in authentic island life away from the busier Santorini hotspots.

Then, it’s time for the wine tasting at Argyros Estate. Located southeast of Fira, this modern winery impresses with its spacious tasting room and views of the vineyards. You’ll sample four different wines, learning about local varieties and wine-making methods. According to travelers, this part of the tour is a real treat—both for the palate and the insights from the knowledgeable staff. One reviewer called their guide a “terrific photographer,” adding a personal touch to the experience.

Finally, if you have some energy left, the tour visits Kamari Beach, one of Santorini’s most popular beaches. It’s a black volcanic shingle stretch that’s perfect for a quick stroll or a refreshing dip. While the pebbles might be uncomfortable for walking in flip-flops, bringing beach shoes makes all the difference. The 20-minute stop is enough to enjoy the stunning backdrop of cliffs and relax by the water.

Transport and Overall Value

The tour’s Mercedes minivan ensures a comfortable ride, and the air conditioning keeps everyone cool, even during the warmest months. Being a private tour, the pacing is entirely up to you, avoiding the rush of larger groups. Pickup from most hotels and the Fira cable car station simplifies logistics, especially if you’re arriving on a cruise or staying in different parts of the island.

Priced at around $231.68 per person, the cost might seem high compared to group tours. However, when you consider the private guide, customizable itinerary, and wine tasting experience, it’s actually quite competitive for the personalized level of service. Multiple reviews mention the excellent guide, with one describing the guide as “full of energy, funny, informative,” which adds to the overall value.

Who Will Love This Tour?

If you prefer tailored experiences over cookie-cutter group excursions, this private tour is perfect. It’s especially suitable for couples, families, or groups of friends who want to explore at their own pace. The flexibility to avoid crowds and focus on your interests makes it a good choice for those with limited time or mobility concerns—just let your guide know, and they’ll adapt accordingly.

It’s also ideal for wine lovers who want to taste local varieties and learn about Santorini’s wine-making traditions. The scenic stops appeal to photographers and anyone who appreciates stunning views, while the private setup ensures a more relaxed, authentic experience.

The Sum Up

This private highlights tour offers a thoughtful, flexible way to discover the best of Santorini. You’ll visit iconic sites—like Imerovigli and Oia—without the crush of big crowds, all while enjoying a personalized route curated by a knowledgeable local guide. The inclusion of a wine tasting at Argyros Estate adds a memorable flavor touch that elevates the experience beyond just sightseeing.

While the price is higher than standard group tours, the private nature, customization, and quality of experiences make it a solid investment for those who value comfort, authenticity, and tailored attention. It’s particularly suited for travelers who want a more relaxed, intimate glimpse of Santorini’s beauty and culture.

Overall, if you’re eager to explore Santorini in your own style, this tour promises a rewarding, memorable day—balanced between scenic beauty, cultural charm, and delicious local wines.

FAQ

Is this tour suitable for children?
The minimum age for this tour is 18, so it’s geared toward adults. Children must be accompanied by an adult.

What is included in the price?
The price covers wine tasting, bottled water, a local experienced guide, private transport, and hotel/port pickup and drop-off. The wine tasting fee at Argyros Estate is included.

Can I customize the itinerary?
Yes, the tour is private and flexible. You can work with your guide to choose your preferred highlights or skip certain stops.

How long does the tour last?
It lasts approximately 4 hours 40 minutes to 5 hours, giving you plenty of time to explore without feeling rushed.

Are transportation and pick-up provided?
Yes, door-to-door pickup and drop-off are included, even from hotels across the island or the Fira cable car station.

What if I have mobility issues?
The guide can adjust the route to accommodate mobility concerns, avoiding too many steps if needed.

Is there a specific time I should book?
Most travelers book about 6-7 months in advance—on average, 201 days ahead—so planning ahead ensures availability.

What should I bring?
Comfortable walking shoes, sun protection, and a camera are recommended. The tour provides bottled water, but bringing your own snacks or additional drinks is fine.

In essence, this private Santorini tour offers a personalized, relaxed, and authentic way to get to know the island’s top sights, savor local wines, and experience the true spirit of Greece’s most famous island.