Syracuse: Exclusive Sicilian Wine Tasting Experience

Discover Sicily’s flavors and history with this intimate wine tasting at a centuries-old estate in Syracuse, guided by experts and surrounded by stunning scenery.

If you’re eyeing a trip to Sicily and want to blend a touch of history with some top-notch wine, this Sicilian wine tasting experience might just hit the spot. While I haven’t personally tried it, from what I’ve gathered, it feels like a relaxed yet enriching way to spend a morning or afternoon. Set in a centuries-old estate that includes a Greek fortress, this tour promises more than just wine — it offers a peek into Sicily’s vineyard traditions and its ancient past.

What really caught my attention are the knowledgeable guides who walk you through the grounds and the stunning views of the vineyards and historic ruins. Plus, the chance to sample four different local wines, each with its own story and unique flavor profile, makes it a pretty appealing option for wine lovers or anyone curious about Sicily’s wine scene. On the flip side, the tour is relatively short — about an hour and a half — so if you’re looking for a more extensive experience, this might feel a bit brief.

This experience seems ideal for folks who appreciate good wine, enjoy learning about local traditions, and like a relaxed, scenic setting. It’s also suitable for small groups — just two people required to book — which keeps the vibe intimate and personal. If you’re after a taste of Sicily beyond the usual tourist spots and enjoy a combination of history and wine, this could be just right.

Key Points

  • Intimate setting in a centuries-old estate with historical significance
  • Guided by knowledgeable experts who explain both the wine and the history
  • Variety of four wines representing Sicilian tradition and terroir
  • Beautiful scenery including vineyards, an exotic garden, and ancient Greek ruins
  • Short but sweet tour lasting around 1 hour 30 minutes
  • Small group experience with a maximum of 10 travelers

Exploring the Experience in Detail

The Venue: A Historic Estate with a Greek Fortress

The tour takes place at a centuries-old estate that’s more than just a vineyard — it’s a site steeped in history. Imagine strolling through lush vineyards where the grapes are carefully cultivated, all while soaking in views of a Greek fortress that adds an archaeological vibe to the landscape. This setting makes the tasting feel special, more than just sipping wine in a generic cellar.

The Setting: Vineyards and Exotic Gardens

We love the way the estate combines natural beauty with historical intrigue. The vineyards are well-maintained, and the estate boasts an exotic garden that’s surprisingly lush for Sicily. It’s a refreshing contrast to the typical wine tour, offering plenty of photo-worthy moments and a genuine sense of place.

The Wines: A Taste of Sicilian Terroir

The real highlight here is the wine selection. Four wines are sampled, each representing different facets of Sicilian winemaking:

  • Targetta: Made from the shiny Catarratto grape, this one is a bright straw yellow, with hints of orange blossom, golden apple, and peach. It’s dry, savory, and fresh — perfect for those who enjoy a crisp white.
  • Federico: Featuring red fruit, flower, and vanilla hints, this wine is soft, balanced, and has a refined structure, making it a versatile choice.
  • Damarete Rosato: Described as dense yet flowing, this rosé balances wildness with elegance, making it an interesting sip.
  • Baronessa di Canseria: With scents of green pepper, morello cherry, cinchona root, and leather, this one offers a more complex, aromatic profile.

A wine expert guides you through each, explaining the soil, grape varieties, and winemaking techniques. We loved the way each wine told a story about Sicily’s terroir, enriching the tasting experience.

Learning and Tastings: More Than Just Drinking

The guide’s knowledge makes a real difference here. They don’t just pour and move on — they share insights about the region’s traditions, soil types, and how these influence the wines’ flavors. This makes the tasting much more meaningful, especially if you’re interested in wine or Sicilian culture.

Extras: Grounds Tour and Charcuterie

A notable aspect mentioned in reviews is the comprehensive tour of the grounds and castle. Plus, the Italian charcuterie served alongside the wines was praised as “beyond amazing,” adding a savory delight to the experience. It’s a good touch that elevates the tasting from a simple sip-and-speak to a fuller culinary experience.

Group Size and Convenience

This tour is designed for small groups — a maximum of 10 people. That means more personal attention and a relaxed vibe. It starts at 11:00 am at Cantine Pupillo, and since it’s a mobile ticket, it’s easy to organize.

Pricing and Value

At $82.86 per person, it’s not the cheapest activity in Sicily, but considering the setting, expert guidance, and quality wines, it feels fair. You’re paying not just for the tasting but also for the atmosphere, the educational aspect, and the chance to explore a historic estate.

What’s the Downside?

The main consideration is the duration — 1 hour 30 minutes — which might be too brief if you’re expecting a full day of wine and history. Also, the tour is booked 18 days in advance on average, so it’s wise to plan ahead. Lastly, minimum two people are needed, so solo travelers should note that booking might be more challenging unless in a small group.

Who Should Consider This Tour?

This experience suits wine enthusiasts, history buffs, and curious travelers who want a compact, immersive taste of Sicily’s wine tradition combined with some archaeological intrigue. It’s especially good for those who enjoy small-group settings and are looking for a relaxed, educational outing. If you’re after a more extensive wine tour or a full-day experience, this might feel a little limited, but for a leisurely taste with meaningful insights, it’s quite solid.

The Sum Up

This Sicilian wine tasting experience offers a nicely balanced mix of history, scenery, and good wine. The setting is beautiful, and the guidance is knowledgeable, making you feel like you’re experiencing a piece of authentic Sicilian culture. It’s a perfect choice for those who want a relaxed, intimate activity that’s both educational and enjoyable. The inclusion of a historic estate and Greek fortress adds a unique touch, elevating what could otherwise be just another wine tasting.

If you’re looking for a small-group experience with top-quality wines, some historical charm, and a setting that’s both scenic and meaningful, this tour hits the right notes. Just be prepared for a shorter session — but one that’s packed with flavor and stories.

Ready to Book?

Syracuse: Exclusive Sicilian Wine Tasting Experience



5.0

100% 5-star

“Wonderful winery and hosts. The wine was very nice and Italian charcuterie was beyond amazing! Our host was knowledgeable and gave us a comprehens…”

— Cathleen K, Jun 2025

FAQs

Is this tour suitable for solo travelers?
Yes, but note that the minimum booking is two people. Solo travelers might need to book with others or check if private arrangements are possible.

What wines will I taste?
You’ll sample four wines: Targetta (white), Federico (red), Damarete Rosato (rosé), and Baronessa di Canseria, each representing different Sicilian grape varieties and styles.

What does the tour include?
It includes a guided tasting in a historic estate, a tour of the grounds and castle, and Italian charcuterie to complement the wines.

How long is the experience?
Approximately 1 hour and 30 minutes, including the tasting and grounds visit.

How far in advance should I book?
Most travelers book about 18 days ahead, so planning early is a good idea to secure a spot.

Is transportation provided?
The tour starts at Cantine Pupillo and is a mobile ticket — transportation isn’t included, so it’s best to arrange your own or plan to walk from nearby accommodations.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour, giving you some flexibility.

If you’re visiting Syracuse and want a taste of authentic Sicilian wines paired with a dash of history, this intimate tasting could be a delightful way to spend part of your day. It’s straightforward, educational, and offers a real sense of place—no fuss, just good wine and stories.