Last Updated on January 19, 2026
We recently visited five wineries in Tuscany, Italy – each with its own story, charm, and character. In this post, we’re sharing why we chose them and our honest impressions of all five – including what we loved and what didn’t quite hit the mark.
Use this guide if you’re deciding which winery tours to do in Tuscany.
But first, a little background on us and what we were looking for in a Tuscan winery experience:
- We love Italian wine, but we’re by no means experts. We generally know what we like, but we don’t have a favorite winemaker or vintage – we just drink what tastes good.
- We wanted our winery visits to feel authentically Italian, so the atmosphere and setting mattered just as much as the wine itself.
- We gravitate toward smaller wineries that offer a more personal, intimate experience rather than large, high-volume operations.
- We knew we wanted to visit a few wineries in the Chianti region (since Chianti Classico is our favorite at home) and at least one Brunello producer in the Montalcino area.
So, with that in mind, here are the five wineries we toured – in the order we visited them.
De’Ricci Cantine Storiche – Montepulciano
The experience: We joined a 75-minute historic cellar tour and wine tasting featuring six wines, including a Vino Nobile di Montepulciano and a Rosso di Montepulciano – both local specialties.
Why we picked it: We were already planning to explore Montepulciano and had read that the underground cellars were a can’t-miss experience. De’Ricci kept popping up with rave reviews, and the photos of its ancient cellars sealed the deal.
What we loved: Seeing the cellars in person was breathtaking – they’re massive, full of history, and so authentically Italian. Our guide, Emilio, a certified sommelier, was excellent and made the wine tasting both educational and fun.
What didn’t quite hit the mark: Honestly, nothing. The experience felt intimate, authentic, and the wine was excellent. This was our first winery of the trip, and De’Ricci set the bar high!
Ciacci Piccolomini d’Aragona – Montalcino
The experience: We booked a 90-minute winery tour and “Rare Italian Style” tasting featuring four wines, including two Brunellos.
Why we picked it: We couldn’t visit Montalcino without tasting Brunello. Ciacci Piccolomini d’Aragona came highly recommended – and their tour time fit perfectly with our schedule.
What we loved: The setting is everything you imagine Tuscany to be – sweeping panoramic vineyards views and a relaxed, personal vibe. It was just the two of us and our guide, Shanel, who was wonderful. The tasting felt private and unhurried, with generous pours in our own tasting room. We even enjoyed our final glasses while strolling the grounds and soaking in the views. We would have stayed all afternoon if we’d had more time!
What didn’t quite hit the mark: Again, nothing at all. We had so much fun and were now officially two-for-two on incredible winery tours in Tuscany!
Podere Campriano – Greve in Chianti
The experience: We took part in a hands-on cooking class at Podere Campriano, which included a tasting of four Chianti Classico wines and a tour of their boutique winery.
Why we picked it: We stayed at this family-run agriturismo for three nights, drawn by its intimate family atmosphere, beautiful setting overlooking Greve in Chianti, and highly rated cooking class.
What we loved: Wow – where to begin? Our stay at Podere Campriano was unforgettable, and the cooking class turned out to be the highlight of our entire trip. We sampled their Chianti Classicos while cooking, which made the experience even more fun. Midway through, we toured the small winery and learned about the family’s traditional winemaking methods.
What made the experience truly special was the personal connection with Elena and Pietro, who made us feel like old friends. The food we created was delicious, but their wines stole the show. Their Chianti Classico became our favorite wine among all five wineries we visited in Tuscany.
What didn’t quite hit the mark: Absolutely nothing. By this point we were smiling ear to ear – not just from the wine, but from three incredible winery experiences in three days.
Montefioralle Winery – Montefioralle
The experience: We joined a 75-minute late afternoon tour and tasting of four wines, including two Chianti Classicos.
Why we picked it: Montefioralle Winery was just a stone’s throw from where we were staying in Greve in Chianti. We’d read glowing reviews of both the winery and the charming medieval village of Montefioralle.
What we loved: The views from the winery were superb, especially looking back towards Montefioralle from the outdoor tasting patio. The atmosphere felt cozy and personal – just us, one other couple, and our guide, who was part of the family that owns the winery. Their variety of wines was also impressive for such a small winery.
What didn’t quite hit the mark: Our guide was knowledgeable but not particularly engaging, and we never felt much of a personal connection. It also felt a bit rushed. Overall, we enjoyed the experience but weren’t as wowed as we had been earlier in the trip.
Ricasoli Winery at Brolio Castle – Gaiole in Chianti
The experience: We booked a 45-minute wine tasting in the Limonaia of Brolio Castle.
Why we picked it: Ricasoli Winery has been owned by the same family for 32 generations and has produced wine since 1141! That incredible history alone made it a must-visit.
What we loved: Brolio Castle and its surroundings are absolutely stunning – worth visiting even if you’re not into wine. From the scenic drive to the castle to the manicured grounds, every view feels picture-perfect. We loved wandering through the vineyards and capturing gorgeous photos along the way.
What didn’t quite hit the mark: The Limonaia is a very modern bar area with beautiful vineyard views, but it lacked a rustic, old-world Tuscan feel. The wine tasting itself was enjoyable but a bit too commercialized, with a video presentation playing on a large-screen TV. We also would have loved to see more of the castle’s interior, but that wasn’t included in this particular tasting.
Overall, the castle was breathtaking, but the wine experience itself fell short. In hindsight, we should have opted for their longer “classic tour” which includes both the winery and castle interior. That likely would’ve given us more of the Tuscan experience we were hoping for.
Our Takeaways from Touring 5 Tuscan Wineries
All in all, we had an incredible time visiting these five wineries in Tuscany. Each offered something unique – from centuries-old cellars to cozy family-run estates – and even the few misses taught us what we value most in a winery experience.
With so many wineries to choose from, we hope this guide gives you some insight and direction as you plan your own Tuscany wine adventure.
Have questions or want to share your favorite Tuscan winery? Leave a comment below – we’d love to hear from you!
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