Tuscany is more than a postcard-perfect destination—it’s a living, breathing region where history, wine, and architecture intertwine. Stretching from the rolling hills of Chianti to the medieval streets of Montepulciano and Montalcino, this part of central Italy is home to some of the world’s most celebrated wine regions.
In Italian, Castello means "castle"—and in Tuscany, many have become working wineries. Often perched on hilltops with sweeping views, these estates are rich in heritage and surrounded by vineyards that have shaped the culture for centuries. Florence, Siena, and Arezzo are ideal base cities for exploring the area, offering easy access to the countryside and its storied estates.
Castle wineries here offer more than tastings—they’re living spaces shaped by stone, oak, and time. Many provide guided vineyard walks, vertical tastings, cellar tours, and access to private collections. Some offer elegant accommodations or host cooking classes and seasonal harvest experiences.
Below, you’ll find a selection of medieval estates that capture the true essence of Tuscany—not just in their architecture or wines, but in the way they carry centuries of tradition with quiet pride. Authentic, grounded, and ever-evolving, they invite you to experience Tuscany not as a visitor, but as a welcomed guest.
Castello Sonnino – The Castle of Dreamy Wines
In the heart of Chianti, Castello Sonnino is where medieval soul meets modern elegance. Once a noble stronghold, this historical estate now pulses with the energy of refined winemaking. Take a guided tour through frescoed halls and aging cellars, then savor a tasting with views over the vineyards. Whether it’s velvety Chianti or rich Vin Santo, Castello Sonnino captures the spirit of Tuscany.
Castello Sonnino - Wine Tasting Gourmet (Tuscany, Italy)
Just 20 minutes from Florence, tucked into the quiet folds of Chianti’s hills, Castello Sonnino seduces with old-world charm and aristocratic flair. This 16th-century castle estate—still home to the Baron and Baroness de Renzis Sonnino—is more than a winery. Walk its sun-washed terraces and you’ll taste the past in every pour—bold reds like the San Leone Merlot and Chianti Montespertoli, all born from estate-grown grapes.
The castle’s cellars, lined with aging barrels beneath vaulted ceilings, are the heart of its slow magic. From small-batch olive oil to expressive blends of Sangiovese, Malbec, and Viognier, everything speaks of care, lineage, and taste.
Castello di Radda: Tradition Reimagined
Set amid the classic hills of Chianti Classico, Castello di Radda is modern in vision but deeply respectful of its roots. This historic winery in Tuscany is known for precision winemaking and sustainability. Castello di Radda produces pure, expressive wines shaped by their terroir. It's a must for any wine enthusiast craving authenticity with a contemporary twist.
Castello Di Radda - Advanced Tasting of Castello di Radda’s finest wines (Tuscany, Italy)
Experience pure Tuscan indulgence with Castello di Radda’s most refined tasting experience. Led by a seasoned wine expert, you’ll explore six standout wines that reveal the depth and personality of the estate. Start with the bright, fresh Chianti Classico DOCG 2022, followed by the graceful structure of the Riserva 2020. Then comes the star—Gran Selezione Vigna Il Corno 2017, a bold and layered expression of Chianti heritage.
Continue with two powerful vintages of the Super Tuscan Guss (2016 & 2015), before ending on a rare, golden note: the Vin Santo del Chianti Classico Occhio di Pernice 2018. A private, seductive tasting for 2 to 8 guests—red, rosé, and deep Tuscan pleasure in every glass.
Castello di Meleto – Bridging Heritage and Modern Excellence
Originally a fortress against Florentine invasions, Castello di Meleto is a beacon of Tuscan charm and winemaking excellence. Just outside Gaiole in Chianti, this castle winery in Tuscany combines centuries-old history with organic farming and state-of-the-art techniques. Enjoy a guided tasting inside the ancient stone walls or stay overnight in one of the castle suites. Their Chianti Classico Riserva is a highlight, as is their experimental range of sparkling wines.
Castello di Meleto - Castle Tour with Wine Tasting Paired with a Light Lunch (Tuscany, Italy)
Begin your journey with a guided stroll through lush vineyards and the fragrant Aromatic Garden, culminating at the iconic Big Bench with sweeping views over the rolling Chianti hills. Next, wander through the castle’s elegant noble rooms, admire the charm of the 18th-century theatre, and descend into the historic cellars and Vinsantaia. Finally, taste three fine wines, paired with a light Tuscan lunch and the estate’s olive oil—a true taste of Chianti.
Castello di Selvole – A Blend of Tuscan and French Winemaking
Located just outside Castelnuovo Berardenga, Castello di Selvole is a uniquely blend of Tuscan heritage and French winemaking finesse. This castle winery masterfully combines the robust character of Sangiovese with the elegance and complexity typical of Bordeaux, producing wines that are bold, aromatic, and memorable. The estate’s calm setting is perfect for travelers wanting a genuine Tuscan wine experience, close to Siena and Chianti Classico.
Visitors can explore the estate’s beautiful vineyards and cellars. Castello di Selvole’s Super Tuscan blends and well-structured Chianti wines showcase this cross-cultural passion.
Castello di Selvole - Tasting in the Historic Tuscan Hills of Chianti (Tuscany, Italy)
Wander through the wine cellar—both modern and ancient—where age-old craft meets cutting-edge winemaking. Each corner whispers secrets of the land, promising a rich, sensory experience. Then, settle into an intimate tasting surrounded by oak barrels, savoring three exquisite wines paired with authentic Tuscan bites. From bold reds to seductive dessert wines, you feel the passion and precision behind Castello di Selvole’s craft. This is a seductive escape into Tuscany’s soul, led by hosts who breathe the magic of their terroir.
Castello della Paneretta – Hand-Picked Grapes for Elegant Wines
Castello della Paneretta, one of the oldest estates in Chianti, dates back over 400 years. With 22 hectares of hand-tended vines, this historic winery in Tuscany keeps the tradition alive while focusing on pure, single-varietal Sangiovese. Enter the family-run castle, and you’ll feel time pause. The wines are balanced, food-friendly, and layered – especially their Chianti Classico and rare Canaiolo varietal bottlings.
Castello della Paneretta - Private Tour & Wine Tasting with Light Lunch (Tuscany, Italy)
Enjoy Castello della Paneretta’s world — where history, art, and wine collide. Stroll through vibrant gardens and descend into a historic cellar graced with frescoes by Bernardino Poccetti. Savor three elegant Chianti Classico wines paired with savory cold cuts, creamy pecorino, fresh bread kissed by estate olive oil, and the soul-warming ‘ribollita soup’ with stale bread, cannellini beans, kale or cavolo nero (black cabbage), carrots, onions, and tomatoes. End with velvety Vin Santo and crunchy almond cookies (cantuccini) — a seductive finish to a timeless experience.
Castello di Albola – A Village Upon a Hill
Perched high above the charming town of Radda in Chianti, Castello di Albola is a medieval village wrapped in vines and dreams. With roots stretching back to the 12th century, this Tuscan castle blends ancient history with breathtaking altitude. Their Chianti Classico and Super Tuscans capture hillside power and centuries of winemaking.
For travelers seeking more than just a taste, the true enchantment unfolds on the historic terraces. Imagine tasting rich, age-worthy wines while gazing over rolling vineyards bathed in golden light—pure Tuscan romance in every glass. Castello di Albola gently invites you to lose yourself in its timeless charm, where every moment feels like a secret worth savoring.
Castello Di Albola – Albola Premium Experience (Tuscany, Italy)
Stroll through sun-drenched vineyards, discover the enduring beauty of the ancient Borgo, and step into historic cellars rich with tradition. Then, indulge in a private tasting of four exceptional Estate Crus, expertly paired with heartfelt Tuscan dishes crafted by their dedicated Chef. Feel the bright, crisp notes of Poggio alle Fate Chardonnay, the layered elegance of Marangole Chianti Classico Gran Selezione, the bold richness of Il Solatìo Chianti Classico Gran Selezione, and the luscious sweetness of Vin Santo del Chianti Classico.
Why Visit a Castle Winery in Tuscany?
From the sun-drenched hills of Montalcino to the medieval charm of San Gimignano, each historic winery reveals a distinctive blend of heritage and terroir, producing wines that seduce the senses and capture the essence of Tuscany. Wander ancient halls, taste wines shaped by centuries of expertise, and feel the magic of places where history and winemaking merge nicely. It’s a sensual escape into the heart of Italian elegance.
Winera makes this experience smooth and memorable. Discover the finest historic wine estates in Tuscany with expertly curated tours, insider access, and personalized tastings designed for true wine lovers. Ready to taste history? Start your journey with Winera today and let Tuscany’s noble wines tell their story. Book your exclusive Tuscan castle winery tour with Winera now!
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