Santorini Private Highlights Tour & Wine Tasting with local guide

Santorini Private Highlights Tour & Wine Tasting with Local Guide

If you’re visiting Santorini for the first time and want more than just postcard-perfect photos, this 5-hour private tour offers a genuine taste of the island’s beauty, history, and culture. Led by knowledgeable local guides, you’ll visit some of the most famous spots, from volcanic beaches to charming villages, all while learning what makes Santorini so unique. For $178.22 per person, this experience promises personalized attention and a blend of sightseeing, storytelling, and a memorable wine tasting session.

Two things we really appreciate about this tour: first, the flexibility offered by a private guide means you get to focus on what interests you most without feeling rushed. Second, the inclusion of a wine tasting at a contemporary winery with stunning art exhibits is a delightful surprise in a landscape often overshadowed by its natural beauty.

A potential consideration is the price — while it’s excellent value for a private experience, it might feel steep for those on a tight budget. Also, given the tour’s focus on highlights, travelers looking for off-the-beaten-path or very detailed archaeological insights might find it a touch superficial.

This tour is perfect if you’re after a comprehensive, flexible, and engaging overview of Santorini’s top sights in a short time. It’s especially suited for first-timers, couples, or small groups who value good storytelling, stunning views, and a taste of local wine. If you want a curated experience that balances sightseeing with cultural flavor, this tour delivers.

Key Points

• Personalized Experience: Private guide ensures a flexible, tailored tour.
• Stunning Views & Iconic Spots: Visit the most photogenic locations like Red Beach, Oia, and Pyrgos.
• Engaging Narration: Guides reveal much of Santorini’s stories and secrets.
• Wine Tasting: Enjoy local wines in a unique winery with art exhibits.
• Comfort & Convenience: Air-conditioned vehicle and hotel pickup make logistics a breeze.
• Time-Efficient: Covers at least 5 key spots in about 5 hours, ideal for short stays or cruise passengers.

A Deep Dive Into the Santorini Highlights Tour

What This Tour Offers in a Nutshell

This private tour is designed for travelers who want to see the essence of Santorini without the hassle of self-driving or joining large groups. For roughly $178 per person, you get around five hours of expert-guided exploration, including transportation in a comfortable, air-conditioned vehicle, and the chance to taste some of the island’s best wines.

The tour covers seven key stops, each chosen for their visual appeal, cultural significance, or both. From volcanic beaches to medieval villages and art-filled wineries, it balances natural beauty, history, and local lifestyle.

The Itinerary: A Closer Look

Red Beach kicks off the tour. Known for its vivid red volcanic sand and dramatic cliffs, it’s a must-photo stop. While accessible from Akrotiri, parts of the beach have become inaccessible since 2013 landslides, so the visit is mostly about the view—and the photo opportunities. Travelers consistently mention how breathtaking the scenery is, with one reviewer noting, “the island of Santorini is beautiful but if you don’t know your way around, you miss its true beauty.”

Next, you’ll visit Perissa Black Sand Beach, the island’s longest stretch of volcanic sand. It’s perfect for a quick stroll or just to take in the crystal-clear waters. Its remoteness from heavily trafficked spots provides a more relaxed vibe, and many reviews praise the opportunity to just soak up the Aegean Sea’s calm.

Moni Profiti Ilia, or Prophet Elias Monastery, offers a panoramic view from the island’s highest point. Sitting at around 567 meters, it’s a simple but powerful spot for photos and reflection. The guide’s storytelling about the monastery’s history enhances the experience, according to guests.

Pyrgos, the charming hilltop village, is a highlight. Built in a medieval style, with narrow streets, fortified walls, and panoramic views, it remains less touristy than Fira or Oia. Travelers love wandering its labyrinthine alleys, discovering hidden corners, and imagining what it was like centuries ago. One reviewer states, “Pyrgos is a typical example of medieval architecture and one of the least spoiled villages by tourism.”

The Art Space Winery is a true standout. Housed in an old pumice stone winery from 1861, it’s a fusion of art and wine. Visitors can explore contemporary Greek art, sculpture, and then sample four local wines in a setting that’s both historic and creative. Many reviews mention how this stop isn’t just about drinking wine but experiencing local craftsmanship and passion for art.

Stopping at the Three Bells of Fira, a blue-domed church with three bells perched above cliffs, offers iconic views of the caldera. It’s a classic photo spot, but the crowds can be intense, so arriving with a guide who can help you get a good shot is a bonus.

Finally, the tour concludes in Oia, the world-famous village of white houses, blue-domed churches, and narrow paths along the volcanic rim. Many find Oia’s charm in its authentic feel—a place where history and modern living blend seamlessly. It’s a perfect spot for last-minute photos and soaking in the essence of Santorini.

The Guide Experience: Knowledgeable and Friendly

From reviews, guides like Elias, Theo, and Theodore consistently receive high praise. Travelers mention guides going above and beyond, being friendly, knowledgeable, and skilled at capturing memorable photos. One guest describes a guide who “made sure we saw all the best places and learned a lot of history,” which makes a big difference when you’re trying to pack a lot into a short time.

The Wine Tasting: More Than Just Drinking

The included wine tasting at Art Space Winery is not just about sipping. It offers a glimpse into traditional winemaking techniques and renowned local wines. Guests often comment on the quality of the wines, especially the notable sweet wines. The art exhibits within the winery add a cultural layer to the experience, making it feel less like a tourist trap and more like a curated cultural visit.

Transportation & Comfort

The private, air-conditioned vehicle ensures a comfortable ride between stops, especially important on hot days. Many reviews emphasize the professionalism of the driver and the convenience of hotel pickup—no need to worry about navigating or parking.

The Value in Context

While the cost might seem high, the value comes from personalized attention, expert guidance, and covering multiple key sights in just five hours. For travelers with limited time, especially cruise passengers or those on a tight schedule, this tour maximizes what you see without feeling rushed.

Who is This Tour Best For?

If you prefer customized, intimate experiences where you get to ask questions and choose what interests you, this private tour is ideal. It’s perfect if you’re craving authentic stories, scenic views, and a taste of local culture. It’s especially suited for first-time visitors, couples, or small groups who want to see Santorini’s essentials without the hassle of self-navigation.

Those who might prefer more archaeological or off-the-beaten-path sites should note this tour focuses on iconic highlights, so it’s best for visual beauty and culture rather than deep history or adventure.

Frequently Asked Questions

How long is the tour?
The tour lasts approximately 5 hours, covering seven key stops.

What is included in the price?
Private transportation, bottled water, four local wines for tasting, and guided commentary are included.

Is this a group tour?
No, it’s a private experience, so only your group participates.

Can I customize the stops?
Yes, guides are flexible and happy to adapt the itinerary based on your preferences.

Is hotel pickup available?
Yes, pickup is offered, making logistics simple.

What are the main highlights I will see?
Red Beach, Perissa Black Sand Beach, Prophet Elias Monastery, Pyrgos village, Art Space Winery, Three Bells of Fira, and Oia.

Are the stops accessible?
Most sites are accessible for visitors, but some walking through narrow, medieval streets may be more challenging for those with mobility issues.

How much free time is there at each stop?
Stops range from about 15 to 45 minutes, enough to take photos, browse, and enjoy the surroundings.

Is this tour suitable for children?
Yes, most reviews suggest it’s family-friendly, especially since it’s private and flexible.

What about wine tasting for under 18s?
The wine tasting is for adults (18+), but the tour itself is suitable for all ages interested in sightseeing.

Final Thoughts

This Santorini Private Highlights Tour with Wine Tasting offers a well-rounded, engaging way to capture the island’s essence in a limited time. With knowledgeable guides, stunning views, and a unique art-filled winery experience, it provides a memorable snapshot of what makes Santorini special.

It’s particularly ideal for travelers who value personalized attention, cultural insights, and scenic beauty. The flexibility and in-depth stories help you feel like you’re exploring with a knowledgeable friend rather than just ticking off sights.

While it isn’t cheap, the combination of comfort, expert guidance, and curated stops makes it a strong choice for those wanting to maximize their time on this iconic island. If you’re after a balanced mix of sightseeing, storytelling, and local flavor—and don’t mind splurging a bit—this tour could be your best bet for an authentic Santorini experience.

Happy exploring!