Santorini Highlights Small-Group Tour with Wine Tasting option

Taking a tour of Santorini’s top sights can feel overwhelming—unless you opt for a well-planned, small-group experience like this one from Argyros Travel. This 5-7 hour adventure promises a balanced mix of iconic viewpoints, charming villages, cultural insights, and a touch of local flavor through a wine tasting. What truly shines here is the personal attention you get from knowledgeable guides, ensuring you don’t just see the sights but also understand their stories.

What we love most? The intimate group size of just 12 travelers means more time for questions, relaxed stops, and genuine interactions with your guide, Harry, who visitors describe as charismatic and extremely well-versed in the island’s secrets.

A potential consideration? The tour covers quite a bit of ground, so if you’re not a fan of walking or have mobility issues, some parts—like the winding streets of Oia or the ancient site of Akrotiri—may require a bit of effort.

Who is this for? Perfect for first-time visitors eager to get a snapshot of Santorini’s highlights without feeling rushed, as well as those who enjoy a mix of sightseeing, culture, and local wine. It’s also a great choice if you prefer guided tours with a personal touch and want to avoid the crowds.

Key Points

• Personalized Experience: Small groups ensure personalized attention and the chance to ask questions freely.
• Diverse Itinerary: From stunning villages to archaeological sites, the tour offers a comprehensive snapshot of the island.
• Expert Guides: Guides like Harry and Yoti earn praise for their knowledge, enthusiasm, and ability to avoid crowds.
• Scenic Views & Photo Opportunities: The stops at Oia, Prophet Elias Monastery, and Red Beach promise breathtaking vistas.
• Wine Tasting: The visit to Artemis Karamolegos Winery combines beautiful vineyard views with a four-course tasting.
• Value for Money: For around $85 USD, the combination of transport, expert guidance, and diverse sights makes for pretty good value.

Deep Dive into the Santorini Highlights Tour

Starting Point & First Impressions

The tour kicks off at the Argyros Travel Meeting Point in Thira. From the get-go, it’s clear this is a thoughtfully curated experience—your guide greets you with enthusiasm, ready to share the island’s stories and secrets. The small-group setup (max 12 travelers) means you’re not just another face in a crowd but rather part of a relaxed, engaging journey.

Exploring Oia’s Main Street

Your first major stop is Oia, the postcard-perfect village famous for its whitewashed houses, pastel balconies, and views over the caldera. With nearly an hour to wander, you’ll have time to get lost in its winding streets, duck under bougainvillea archways, and soak in views that countless travelers have marveled at. Reviewers consistently mention how guides like Harry and Jakob take the time to point out the best photo spots—so don’t forget your camera.

Melissa, one traveler, shared, “I learned so much and it didn’t feel rushed or overwhelming.” This highlights one of the biggest advantages: a relaxed pace that balances sightseeing with free time.

Pyrgos & Megalochori: Authentic Greek Villages

Next, the tour visits Pyrgos, a traditional village with narrow alleys and a medieval castle. Reviewers note the charm of Pyrgos, with one mentioning about 20 minutes to explore its quiet streets and historic sites. It’s a great chance to see a less touristy side of Santorini and appreciate local life.

Megalochori is another village you’ll pass through, offering more authentic Cycladic architecture and peaceful vibes. These stops are valued by guests who want to see beyond the typical tourist spots and experience local culture.

The Monastery of Profitis Ilias

Perched at the island’s highest point, this monastery offers sweeping views that are described as “wow-inspiring” by visitors. The 20-minute stop allows for photos and a quick look into monastic life. It’s a fantastic vantage point to understand the island’s geography and get a sense of its tranquility—something that many reviewers praise as a highlight.

The Winery Experience

No visit to Santorini is complete without wine, and the Artemis Karamolegos Winery offers a scenic setting for a 4-course tasting. Guests often rave about the views overlooking vineyards and the quality of the wines, with some reviewers mentioning that the wine tasting alone makes the tour worthwhile. The tasting costs $20 per person and includes a selection of local varietals.

Melissa called this a “beautiful winery,” emphasizing the experience of sipping wine in such a picturesque location. The guides, like Constantine, are praised for their knowledge, making the tasting both educational and relaxing.

Archaeological Marvel: Akrotiri

Dubbed the “Pompeii of the Aegean,” Akrotiri’s excavations reveal an advanced prehistoric city buried under volcanic ash. Entrance costs $20, but the hour-long visit provides fascinating insights into Minoan civilization. Reviewers who’ve visited note the detailed frescoes and the importance of this site in understanding Santorini’s ancient history.

Harry, the guide, is appreciated for making the site accessible and interesting, even for those not normally big on archaeological sites.

The Red Beach & Scenic Outlooks

The tour includes a quick stop at the Red Beach Viewpoint, which offers a dramatic vista of red cliffs and turquoise waters. It’s an ideal spot for photos and a moment to appreciate the island’s volcanic origins. Reviewers mention this as a “breathtaking” viewpoint and a favorite for Instagram-worthy shots.

Emporio Village: A Hidden Gem

Finally, the tour concludes in Emporio, a traditional village with a medieval Kasteli and Cycladic architecture. With about 45 minutes here, you can stroll narrow alleys and soak in local life far from the tourist crowds. Guests appreciate these authentic, less-visited areas, describing the experience as “charming” and “informative.”

What Makes This Tour Stand Out?

Knowledgeable Guides: The reviews consistently highlight guides like Harry, Jakob, and Yoti for their enthusiasm, local insights, and ability to avoid the crowds. They’re praised for answering questions thoroughly, sharing stories, and finding quieter spots for photos.

Scenic Views and Authentic Spots: The mix of famous viewpoints, traditional villages, and archaeological sites ensures a well-rounded glimpse of Santorini. Many travelers mention how the tour avoids the crowds by timing visits well and taking lesser-known paths.

Wine Tasting Experience: The visit to Artemis Karamolegos Winery is a highlight, with the beautiful vineyard setting and quality wines providing a relaxing end to the day.

Value for Money: For roughly $84 USD, including transport, guide service, water, and entry fees to key sites, this tour packs a lot of value. It’s a comprehensive way to see the major sights without the hassle of organizing your own transportation or worrying about logistics.

Small Group Dynamic: The maximum of 12 travelers makes interactions more personal, and reviewers emphasize how this creates a friendly, unhurried atmosphere. It’s especially appreciated by solo travelers and those new to the island.

Practical Details and Tips

Transportation: The tour uses air-conditioned minivans, ensuring comfort during the island’s sometimes warm or windy days. The driver, Takis, is praised for his skill and friendly attitude.

Timing: The tour operates in all weather conditions, but it’s wise to dress appropriately with sunscreen, a hat, sunglasses, and a jacket for cooler evenings or wind. It starts around mid-morning and typically lasts about 5-7 hours, giving you ample time to enjoy each stop.

Walking & Shoes: Expect some walking on uneven cobblestones and steep paths, so comfy shoes are recommended. Reviewers mention moderate walking involved at sites like Oia, Pyrgos, and Akrotiri.

Booking & Cancellation: The tour is booked on average 33 days in advance, indicating high popularity. It has a flexible cancellation policy—full refund if canceled more than 24 hours in advance.

Additional Costs: The wine tasting ($20) and Akrotiri entrance ($20) are extra, but many guests find these well worth the additional expense for the overall experience.

Who Should Consider This Tour?

This experience is ideal for first-time visitors wanting a well-rounded overview of Santorini’s must-see sights. If you’re someone who appreciates a small, intimate group rather than large bus tours, you’ll particularly enjoy the personal attention and flexibility.

It suits travelers interested in a blend of scenic viewpoints, cultural stops, archaeology, and wine—an excellent choice for those wanting a taste of everything without feeling rushed. Perfect for couples, solo travelers, and small groups eager for meaningful interactions with guides.

Final Thoughts

This Santorini Highlights Small-Group Tour offers excellent value by blending iconic vistas, traditional villages, a historic archaeological site, and a scenic winery. The guides are consistently praised for their friendliness, knowledge, and ability to keep the experience engaging. The small-group format makes the day feel personalized and relaxed, perfect for anyone who wants to explore in comfort without the chaos of larger tours.

While the tour involves some walking and a few extra costs (wine, site entry), many find these are worthwhile investments for a truly memorable day. Whether you’re a first-time visitor or someone eager to see the island’s best without the stress, this tour delivers a balanced, authentic, and enjoyable Santorini experience.

FAQ

Is transportation provided? Yes, the tour includes transport by air-conditioned minivan, which helps make the day comfortable and stress-free.

How long is the tour? The duration is approximately 5 to 7 hours, covering multiple stops across the island at a relaxed pace.

What’s included in the price? The price covers transport, a local guide, bottled water, and all taxes and fees. Entry to sites like Akrotiri and the wine tasting are additional.

Can I cancel if my plans change? Yes, free cancellation is available up to 24 hours before the tour, with a full refund.

Is this tour suitable for everyone? It’s suitable for most travelers who can handle moderate walking. It operates in all weather conditions, but dressing appropriately is advised.

Are there any hidden costs? Aside from the wine tasting ($20) and archaeological site entry ($20), no hidden costs are expected.

In summary, this tour is a fantastic way to see the highlights of Santorini with a personal touch, expert guiding, and a lovely wine tasting to end the day. It’s especially recommended for those who value genuine insights, quality scenery, and a relaxed atmosphere.