Santorini Small-Group Tour with Wine Tasting & Food Pairing

Visiting Santorini is like stepping into a postcard—whitewashed buildings, dramatic cliffs, and deep blue waters. While many travelers stick to the well-trodden paths, this small-group tour offers an insightful and relaxed way to experience the island’s most iconic spots, combined with a memorable wine tasting and delicious Greek food pairing.

What we love most about this experience is the intimate size—limited to just seven participants—which ensures a personal touch and plenty of opportunity for questions. The visit to the ancient city of Akrotiri really stands out, offering a fascinating glimpse into life 3,500 years ago. However, keep in mind that some parts of the tour, like the walk up to Pyrgos castle, involve steps, so it may not be suitable for everyone.

This tour appeals most to travelers who enjoy a mix of history, scenic beauty, local culture, and a relaxed tasting experience. If you’re after a comprehensive yet manageable way to see Santorini’s highlights, this one’s worth considering.

• Intimate small-group setting enhances personalized experience and interaction
• Mix of cultural, archaeological, and scenic stops offers a well-rounded day
• Wine tasting paired with Greek dishes provides authentic flavors and insights
• Visiting iconic sites like Akrotiri and Oia balances history and postcard-perfect views
• Includes hotel pickup and drop-off for easy, stress-free transportation
• Limited availability means booking ahead is recommended

Discovering Pyrgos: A Venetian-Inspired Village

The tour begins with a visit to Pyrgos, a charming village built in the 15th century under Venetian influence. This spot isn’t just picturesque—it’s also historically significant, home to one of the best-preserved castle ruins on the island. As you wander through narrow alleys, you’ll notice the traditional architecture and narrow streets that tell tales of centuries past. Our reviewer Monika appreciated the guide’s detailed explanations, especially about the village’s history and architecture, which added depth to the visit.

Expect a few steps in the process of reaching the castle’s top vantage point, so mobility considerations are worth noting. Still, the panoramic views over Santorini from Pyrgos make the climb worthwhile.

Stepping Back in Time at Akrotiri Archaeological Site

Next is a visit to the Prehistoric city of Akrotiri, buried under volcanic ash around 3,500 years ago. This excavation site is a highlight for those intrigued by ancient civilizations. The tour includes a one-hour stop, which provides plenty of time to explore the well-preserved ruins—though, notably, an expert guide is not included here. Reviewers mention that the site is a must-see, with some describing it as “an archaeological wonder” that offers a real sense of life on the island long before modern Santorini.

The site’s significance lies in its status as the earliest settlement on the island, and walking through the remains gives a tangible connection to the past. Expect to see volcanic ash-preserved buildings, streets, and artifacts that tell stories of a thriving Bronze Age community.

Vlihada and Perivolos Beaches: Unique Natural Beauty

After the archaeology, you’ll visit Vlihada Beach, famous for its striking white volcanic cliffs sculpted by wind and waves. It’s a dramatic landscape, where the black sand of Perivolos Beach also catches the eye. Both beaches stand out for their distinctive volcanic origin, offering excellent photo opportunities and a chance to take in Santorini’s natural artistry.

While these stops are more about appreciating the landscape than lounging, they add a much-needed breather and a chance to marvel at the island’s geological history. We loved the way these beaches highlight Santorini’s volcanic personality and provide a stark contrast to the traditional white buildings.

Exploring Megalochori: A Step Back in Time

The small village of Megalochori is our next stop, dating back to the 17th century and historically linked to the island’s wine trade, particularly Vinsanto—a sweet, fortified wine. Wandering through its quiet streets gives the sense of a true local community, away from tourist-heavy spots. The guide’s insights about local wine production enrich this stop, making it more than just a photo opportunity.

Lunch and Wine Pairing: Flavors of Greece

No visit to Santorini is complete without tasting its wines. The highlight of the tour is a lunch at one of the island’s best wineries, paired with local wines and traditional Greek dishes. Under the guidance of an expert sommelier, you’ll learn about the wines’ characteristics and why they pair so well with local cuisine. Reviewers mention the quality of the wines, noting that the pairing elevates the meal and enriches the experience.

This part of the tour offers great value—it’s not just about eating but understanding how the island’s unique microclimate and volcanic soil influence its wine. The relaxed, friendly atmosphere makes it easy to ask questions and learn about what makes Santorini’s wine special.

Final Stop at Oia: The Iconic Cliffside Village

To wrap up the day, the tour stops in Oia, famed for its stunning sunsets and cliffside allure. Here, you have free time to wander the charming streets, browse boutique shops, and take in the famous views of the caldera. It’s a picturesque ending, and many appreciate having the opportunity to explore at their own pace after the guided portions.

Transportation and Group Size

Transportation is by a designated driver in a small, comfortable vehicle, ensuring a relaxed atmosphere. The group is limited to just 7 participants, which means more personalized attention and fewer crowds. Pickup starts early at around 8:45 am from various hotel points, so confirming your meeting spot with the provider is recommended. This small-group format ensures a quieter, more engaging experience.

Duration and Pricing

The tour lasts about 6 hours, which strikes a good balance between seeing key sights and not feeling rushed. Costing $203 per person, the price covers hotel pickup and drop-off, lunch with wine pairing, and liability insurance. Note that you’ll need to purchase your own tickets to Akrotiri and other sites, but the value comes from the seamless transport, expert commentary, and inclusion of the wine tasting experience.

What to Bring & Considerations

Travelers should bring sunglasses, a sun hat, and comfortable clothes—Santorini can be sunny and warm, especially in the summer. Be prepared for some walking and steps, particularly at Pyrgos and the archaeological site. Oversized luggage isn’t allowed on the vehicle, so pack light. The tour isn’t recommended for those with mobility issues, so plan accordingly.

Authentic Insights from Past Travelers

Reviewers consistently praise the knowledgeable guides and personable drivers. Monika highlighted how the guide did a "great job explaining and showing us everything," mentioning insider tips that made the experience more enriching. The wine tasting and food pairing also received high marks, with guests saying it was an "excellent" way to taste local flavors and learn about Santorini’s wine culture.

Another traveler described the experience as "friendly and interesting," emphasizing the relaxed, engaging atmosphere provided by the small group and professional guides. These personal touches help turn a sightseeing trip into a memorable, educational outing.

This tour strikes a good balance between structured sightseeing and relaxed exploration. It’s particularly suited for those who want a tailored experience without feeling overwhelmed by too many stops or large crowds. The combination of archaeology, scenic beaches, charming villages, and wine tasting offers a comprehensive snapshot of Santorini's highlights in one manageable day.

The inclusion of hotel pickup and drop-off minimizes logistical worries, making it ideal for visitors unfamiliar with the island’s transportation. The small group size ensures a more intimate experience, allowing for genuine conversations and personalized attention—something many travelers value.

What sets this tour apart is the focus on authentic experiences, from the ancient city of Akrotiri to local Greek dishes paired with premium wines. While it may not cover every corner of the island, it offers a well-curated, balanced snapshot designed to leave you with lasting impressions—and perhaps a new appreciation for Santorini’s rich history and vibrant flavors.

If you’re a traveler who enjoys a mix of history, scenic beauty, and a good glass of local wine, this small-group Santorini tour will serve you well. The knowledgeable guides and carefully selected stops ensure you get a genuine taste of the island’s character, without the hassle of navigating alone or rushing through sights.

It’s particularly ideal for those who prefer a more intimate, personalized experience, and don’t mind a bit of walking or steps. With the inclusion of a fantastic wine and food pairing, this tour offers real value—combining education, relaxation, and memorable views in one well-rounded package.

Ultimately, it’s a fantastic way to see some of Santorini’s best bits while indulging in authentic flavors and stories, making it a top choice for your island adventure.

How long is the tour?
The tour lasts approximately 6 hours, providing a thorough yet manageable day of sightseeing and tasting.

What’s included in the price?
The price covers hotel pickup and drop-off, a designated driver, lunch with wine pairing, and liability insurance. Entrance tickets are not included.

Is the tour suitable for everyone?
It’s best suited for travelers without mobility issues due to some steps at Pyrgos and the castle ruins. Oversized luggage isn’t allowed, and the tour isn’t recommended for those with mobility impairments.

Do I need to book tickets in advance?
You’ll need to purchase tickets separately for sites like Akrotiri, but the tour handles transportation and provides a guided experience. It’s advisable to reserve ahead due to limited group size.

Can I customize the experience?
Since this is a pre-arranged small-group tour, customization options are limited. However, the guide’s insights and the visit to multiple sites provide a flexible, engaging experience.

How many people are in each group?
Groups are limited to 7 participants to ensure a personalized and relaxed atmosphere, making for a more engaging experience.