Private 5 Hours Highlights Tour by Native Guide with Wine Tasting

Exploring Santorini: A Personal Touch with a Private Guide and Wine Tasting

If you’re looking to get a genuine feel for Santorini, skipping the crowds and typical tour buses, this private 5-hour highlights tour could be just what you need. Offered by Top Santorini Tours, it promises a customized experience with a local guide, allowing you to explore at your own pace. The idea of building your own itinerary or working with your guide to select highlights makes this stand out from run-of-the-mill group excursions. Plus, a wine tasting at one of the island’s top wineries adds a delicious and memorable local flavor.

What really caught our eye about this tour is the flexibility it offers—you’re not just stuck with a pre-set route, and the private transport means you won’t be racing to keep up with a large group. Plus, the tour’s high rating (a perfect 5.0 based on 25 reviews) and the fact that most travelers book it around 6 to 7 months in advance show it’s a popular choice for those seeking a personalized experience. On the flip side, it’s worth noting that this tour is a bit pricier than typical half-day options, but for the customization and comfort, many find the cost justified.

One thing to consider is that this tour is designed for those aged 18 and above, so it’s not suitable for kids under 18. If you’re after a laid-back, intimate way to see Santorini’s top sights, and you value having a knowledgeable local guide along, this tour might be just perfect. It’s especially well-suited for travelers who appreciate good wine, want to avoid the typical tourist spots rushed through, and prefer a flexible, private experience.

Key Points

• Flexibility and Customization: You have the chance to shape your own itinerary or work with your guide to visit the sights that interest you most.
• Private Experience: Only your group participates, ensuring a personalized and intimate day.
• Stunning Views & Authentic Stops: From the highest villages to iconic sunsets, you’ll see some of Santorini’s most photogenic spots.
• Wine Tasting at Estate Argyros: Tasting four different local wines with ocean views makes for a memorable highlight.
• Comfort & Convenience: Transportation in a private Mercedes minivan, including hotel or port pickup, simplifies logistics.
• Time Management: With around 4.5 to 5 hours, you’ll enjoy a relaxed pace without feeling rushed.

In-Depth Look at the Experience

This tour stands out because it’s truly tailored to your preferences. Unlike large, structured group tours, here you get to decide what parts of the island to visit, and your guide helps craft an itinerary that suits your interests and energy level. Whether you want to explore charming villages, relax on beaches, or take in panoramic views, the guide’s flexibility makes this a perfect fit.

Transportation in a Mercedes Minivan: Traveling in style and comfort, you’ll be driven around by a knowledgeable local driver-guide. This not only boosts the experience but also keeps things smooth—you won’t have to worry about navigating or parking. The private transfers include pickup and drop-off from your hotel, port, or airport, which saves a lot of hassle, especially if you’re arriving by cruise or staying outside the main villages.

Stops and Highlights:

• Firostefani: Starting in this scenic village offers a peek into local life, perched high above Fira. This spot, often called the “Crown of Fira,” is perfect for a quick photo op and soaking in views without the crowds. Since it’s just a 15-minute stop, it’s more about the vibe and scenery than extensive exploring.

• Imerovigli: Known as the highest town on Santorini, Imerovigli boasts quintessential white houses and blue-domed churches. Its preserved architecture provides a glimpse into traditional Cycladic style. Reviews mention the beauty of the views here, and the fact that it remains largely unchanged makes it a more authentic experience.

• Oia: No trip to Santorini is complete without a visit to Oia. Famous for its breathtaking sunsets, but equally magical in the morning or afternoon, Oia’s pastel houses, narrow alleys, and iconic windmills are picture-perfect. Travelers say it’s a relaxed place to wander and enjoy the scenery—great for shopping or grabbing a coffee amid stunning architecture.

• Castelli of Pyrgos: This traditional village is home to a fortress-like castle built around 1580. Its location offers sweeping views of the island’s plains and the Aegean Sea. The review mentions feeling like a local here, and the atmospheric castle provides a charming break from more tourist-heavy spots.

• Estate Argyros: Here’s where the tour really shines for wine lovers. This modern estate, located on the outskirts of Episkopi-Gonia, offers a spacious tasting room with views that complement the wine. Sampling four different local wines is a highlight, especially given the estate’s reputation as the second-largest winery on the island. The tasting lasts about 45 minutes, giving you a chance to relax and soak up the flavors.

• Kamari Beach: Wrapping up the day, Kamari offers a different vibe—beachside relaxation. The black volcanic shingle beach is lively, with plenty of spots to dip your toes in the water. It’s a popular beach, which might mean some crowds, but if you prefer a quieter end, the quieter tip near the big rock could be just right.

Review Insights & Authentic Experiences

Feedback from past travelers paints a clear picture: guides are knowledgeable, personable, and often go out of their way to customize routes based on individual needs. One reviewer mentioned how their guide, Costos, was friendly, fun, and a terrific photographer, adding a personal touch that makes the day special. Others loved the insider tips and the relaxed pace, especially since the tour is private.

The wine tasting at Argyros Estate is highly praised, with many reviewers noting it as a key highlight. Tasting four different wines while enjoying ocean views feels like a genuine slice of local life. The overall value is reflected in the positive reviews, with some mentioning how the guide tailored the day to accommodate mobility issues or personal preferences, which is a nice touch.

What to Expect in Terms of Price and Duration

At roughly $231.68 per person, the tour isn’t the cheapest half-day option but considering the private setup, custom routes, and included wine tasting, it offers solid value. It’s an experience designed for those who want to go beyond the typical tour group—more personalized, relaxed, and immersive.

The tour lasts around 4 hours 40 minutes to 5 hours, which means you get a good chunk of the day without feeling overwhelmed. It’s ideal if you want a highlight reel of Santorini without dedicating an entire day or dealing with large crowds.

Who Is This Tour Best For?

This private tour is perfect for those who prioritize flexibility and personalized experiences. If you enjoy wine and want to incorporate local flavors into your sightseeing, the wine tasting is a natural bonus. It suits travelers who value comfort and a relaxed pace—especially if you’re traveling with someone who prefers avoiding strenuous walking or large groups. While it’s not explicitly family-focused, it’s suitable for adults who want a more refined, intimate glimpse of Santorini.

It’s also a good choice if you’ve already visited the main sights and want to explore less obvious spots, or if you’re arriving by cruise and need a seamless transfer. Keep in mind that it’s geared toward travelers 18 and over, so families with younger children might want to look elsewhere.

Frequently Asked Questions

Is this tour suitable for different mobility levels? Yes, since the tour is private and customizable, guides can adapt the route to accommodate mobility concerns, including fewer steps or less walking.

Can I choose which villages or sights to visit? Absolutely. You can build your own itinerary or work with your guide to select the stops that interest you most.

What kind of vehicle is used? The tour uses a private Mercedes minivan, offering comfort and air-conditioning for a smooth ride.

Does the tour include lunch? No, lunch isn’t included, but you can plan to grab a bite during your time at the various stops, especially in Oia or Kamari.

Are there any additional costs? The wine tasting at Estate Argyros is included in the price, but you’ll need to cover any extra purchases or snacks.

Is this tour available for cruise ship travelers? Yes, the tour offers pickup and drop-off from the Fira Cable Car upper station, making it convenient for cruise passengers.

Can children join this tour? The minimum age is 18, so it’s intended for adult travelers only.

How far in advance should I book? On average, travelers book about 201 days ahead, indicating it’s popular and worth reserving early.

What’s the cancellation policy? You can cancel for free up to 24 hours before the tour, which offers some flexibility if plans change.

Is the tour weather-dependent? Yes, it requires good weather. If canceled due to weather, you’ll be offered a different date or a full refund.

In the end, this private highlights tour offers a fantastic way to see Santorini through a tailored lens, with the bonus of wine tasting and relaxed pacing. It’s best suited for those who value personalization, comfort, and a genuine local experience. Whether you’re there for the scenery, the wines, or simply avoiding the crowds, this tour can give you a memorable slice of Santorini that feels just right.