The Wine Triangle: Montepulciano, Pienza & Montalcino

Three legendary villages. Two of Italy's most prestigious wines. A cheese that conquered Lorenzo the Magnificent. This isn't just a winery tour: it's a journey into the heart of Tuscan food and wine excellence, where every glass tells centuries of tradition and every taste is a sensory experience.

The Wine Triangle takes you from Montepulciano, with its underground cellars carved into tuff and the history-making Vino Nobile DOCG, to Pienza, the UNESCO-listed ideal Renaissance city where pecorino ages in oak barriques acquiring hints of grape marc, and finally to Montalcino, undisputed kingdom of Brunello di Montalcino, the wine the world envies us for.

Two days (or one intensive) to discover that Tuscany's wine country isn't just landscape: it's the art of transforming grapes and milk into masterpieces you experience with all your senses.

The Wine Triangle: three villages, one unforgettable journey

From Montepulciano to Pienza takes just 15 minutes, from Pienza to Montalcino 30. Three excellences within reach, each with its own personality. Vino Nobile tells historic elegance, pecorino in barriques is the perfect meeting of milk and wine, Brunello is power becoming poetry. This isn't a wine itinerary: it's an immersion in the art of transforming extraordinary raw materials into excellences the whole world envies us.

Start from Podere Grotta Antica and discover why Tuscany's food and wine scene is legendary.

DAY 1: MONTEPULCIANO AND PIENZA

Distance from Podere: 40 minutes
Recommended time: 4-5 hours (morning + lunch)

Montepulciano welcomes you perched on a tuff ridge, with 60 meters of elevation gain offering breathtaking views of Val di Chiana and Val d'Orcia. But what it hides beneath the Renaissance palaces makes it unique: a labyrinth of underground cellars carved in the 15th century, where Vino Nobile di Montepulciano DOCG has been aging for over 500 years.

Nobile Wine: Italy's first DOCG
In 1980, Vino Nobile di Montepulciano became the first Italian wine to obtain DOCG status. Minimum 70% Sangiovese base, notes of black cherry, blackberry, forest fruits, violet. Ruby red color that evolves to garnet with aging. A wine that made history.

The unique experience: strolling among cellars
Unlike other wine regions where you need to drive from one scenic winery to another, in Montepulciano you just walk through the historic center: the historic cellars are all beneath Piazza Grande and the medieval streets. Descend into the Gothic-Renaissance depths, among narrow tunnels, stone stairs, barrel vaults and centuries-old casks. The atmosphere is like a wine cathedral.

Cellars to visit:
Contucci (Via del Teatro, 1 - steps from Piazza Grande) - Historic since 1700, one of Montepulciano's oldest cellars still run by the family. Tastings in period settings, tales of generations of winemakers.

De Ricci (Via di Collazzi)
15th-century Gothic-Renaissance underground city. Labyrinth of tunnels, hidden crypts, time-travel atmosphere. The barrels guard Vino Nobile and Vin Santo within walls steeped in history.

Le Berne (outside town center, for those seeking views)
Family-run by Andrea and Federico Natalini. Spectacular panoramic views of vineyards and hills. Traditional artisan wines. Awarded best Nobile di Montepulciano 2018 (93.2 points).

🧺 Podere Advise

For the most authentic experience, choose a historic underground cellar in the center (Contucci or De Ricci): descending into the village's depths is an experience worth as much as the wine itself.

What to see beyond cellars:

• Piazza Grande: The village's Renaissance living room, with Palazzo Comunale (tower with 360° views), Cathedral, Palazzo Nobili-Tarugi
  

• Via di Gracciano del Corso: The main street climbing upward, lined with historic palaces and wine shops
  

• San Biagio Church: Just outside the walls, 16th-century masterpiece by Antonio da Sangallo

  
  Where to lunch:
  

• Osteria Acquacheta: Legendary Florentine steaks, authentic atmosphere, reservations required

• Osteria del Conte: Traditional Tuscan cuisine, elegant yet informal setting

• Il Teatro: Creativity meets tradition, panoramic views

• Rosso Rubino Trattoria: Handmade pici, Chianina ragù, honest prices

STOP 2: PIENZA - The ideal city and kingdom of pecorino

Distance from Montepulciano: 15 minuti
Recommended time: 3-4 hours (afternoon + dinner)

After Montepulciano, fifteen minutes of scenic road through hills and cypresses and you reach Pienza, the "ideal city" commissioned by Pope Pius II in 1459. UNESCO Heritage Site since 1996, Pienza is the first concrete example of Renaissance urban planning: every stone, every perspective, every building dialogues in perfect harmony. A dream of beauty turned to stone.

The story: from Corsignano to Pienza

In 1405, Enea Silvio Piccolomini was born here, becoming Pope Pius II in 1458. Returning to his native village of Corsignano, horrified by its decay, he decided to transform it into his "ideal city." He entrusted the project to architect Bernardo Rossellino (student of Leon Battista Alberti) who in just 4 years (1459-1462) redesigned the village applying principles of Renaissance humanism. Pienza - "city of Pius" - was born.

Must to see:

• Piazza Pio II - Heart of the ideal city. Perfectly proportioned trapezoidal square, surrounded by:

• Cathedral (Cathedral of the Assumption): Renaissance façade, German Gothic interior (commissioned by the Pope as tribute to Germanic tradition), extremely bright windows

• Palazzo Piccolomini: Pope's summer residence, inner courtyard with loggia and hanging garden with breathtaking Val d'Orcia views

• Palazzo Comunale: Elegant loggia, tower

• Palazzo Borgia: Now Diocesan Museum with sacred art

• Corso Rossellino - Gourmet shopping street

  The main axis connecting the two medieval gates. Here artisan shops of pecorino, cured meats, wines, honey concentrate. Every 10 meters a different aroma stops you.

🧺 Podere Advise

Visit Pienza in late afternoon: the grazing sunset light ignites the square's travertine with unforgettable warm gold. And the shops are still open for purchases.

Il Pecorino di Pienza: cheese of the gods

Pienza is the undisputed capital of pecorino. But not just any pecorino: here they produce Pecorino di Pienza aged in barriques (PAT - Traditional Agricultural Product), an excellence that Lorenzo the Magnificent himself came to taste.

The secret:

• Unique clay soils: Sheep graze on wild herbs (wormwood, soapwort, wild mint) giving the milk hints of chestnut, bay leaf, herbaceous notes

• Sardinian breed sheep: Tradition brought by Sardinian shepherds who migrated to Tuscany

• Aging in oak barriques: Forms rest at least 90 days in the same barrels that contained wine, acquiring tannic aftertaste and grape marc notes

  The result: white rind with violet shades, straw-colored paste, intense flavor with unmistakable wine notes.

  Where to buy pecorino:

  Cugusi - The absolute reference (Podere's recommendation)
  Careful selection, possibility to taste before buying, passionate explanations about production.

Unique experience

Fiera del Cacio (first Sunday of September): popular festival with "Palio del Cacio al Fuso" - the town's six districts compete throwing pecorino wheels toward a central target. Tastings, stalls, medieval atmosphere.

DAY 2: MONTALCINO - The kingdom of Brunello

Distance from Pienza: 30 min
Distance from Podere: 1 hour
Raccomanded time: full day

If Montepulciano is historic elegance and Pienza is Renaissance harmony, Montalcino is pure power. Here Brunello di Montalcino DOCG is born, the world's most famous Italian red wine, the one international connoisseurs venerate and collect.

Brunello: 100% Sangiovese Grosso

Unlike Vino Nobile (Sangiovese + other grapes), Brunello is 100% Sangiovese Grosso, the local clone called "Brunello." Minimum 2 years aging in oak + 4 months in bottle (Annata) or 6 months (Riserva). Release for consumption: from January 1st of the 5th year after harvest (6th for Riserva).

Result: wine of extraordinary body, elegance, complexity, decades-long aging potential. Prices starting from €30-40 and reaching €300-500 for Riservas from iconic wineries.

The territory:

Montalcino rises on a 564m hill, surrounded by holm oak and strawberry tree woods. 15% of the territory is covered by vineyards (about 2,000 hectares). 250 producers. Over 6 million bottles annually. UNESCO World Heritage since 2004.

What to see:

The Fortress (1361) - Perfectly preserved pentagonal castle. Walk the rampart walkways for 360° views of vineyards, Val d'Orcia, Monte Amiata. Inside: wine shop with Brunello selection (tasting available), cultural events.

Historic center - Intact medieval village with narrow streets, small squares, stone palaces, wine shops at every corner.

Wineries to visit:

La Sesta di Sopra ⭐
Artisan winery, warmest welcome, great professionalism. Podere arranges tastings for you - contact us to book. A personalized, authentic experience, far from mass tourism.

Biondi Santi (optional - historic icon)
The winery that "invented" modern Brunello. Clemente Santi in 1800, then Ferruccio Biondi Santi who created the first Brunello from selected 100% Sangiovese grapes. History, legend, significant prices.

Casanova di Neri (optional - modern excellence)
Two legendary labels: Cerretalto and Tenuta Nuova, considered among the absolute best Brunellos. Even the White Label (more accessible) is very high quality.

🧺 Podere Advice

Trust us for Sesta di Sopra: we arrange personalized tastings with our partners. You'll have an authentic experience, relaxed pace, chance to ask questions and discover Brunello told by passionate producers.

Where to lunch:

Boccon Divino
Well-executed traditional Tuscan cuisine, excellent wine list (obviously), welcoming atmosphere. Perfect for pairing Brunello with pici with wild boar ragù or Chianina tagliata.

🧺 Podere Advice

In Montalcino always order a meat course (wild boar, Chianina) with a glass of Brunello. It's the pairing the territory has demanded for centuries.

IF YOU HAVE ONLY 1 DAY: THE CONCENTRATED ROUTE

Don't have two days? Focus on Montepulciano + Pienza (55 minutes total from Podere, 15 minutes between them).

Intensive 1-day program:
- 9:00 - Departure Podere → Montepulciano (40 min)
- 9:40-11:30 - Montepulciano: Underground cellar visit + Piazza Grande stroll
- 11:45 - Transfer to Pienza (15 min)
- 12:00-13:30 - Pienza: UNESCO center visit, pecorino shopping, light lunch
- 14:00-16:00 - Wine + cheese tasting at leisure in panoramic wine shop
- 16:30 - Return to Podere (35 min)

Alternative 2: Montalcino + Pienza (leaving Montepulciano for another time)

🌟 SPECIAL EXPERIENCES BOOKABLE THROUGH PODERE

Beyond independently visitable wineries, Podere Grotta Antica arranges unique experiences you won't find elsewhere:

🍷 Tasting at La Sesta di Sopra (Montalcino)
Personalized Brunello tasting arranged directly by us. Family welcome, relaxed pace, chance to dialogue with producers. The authentic Brunello experience.

🏛️ Santa Mustiola - The winery in an Etruscan tomb
The experience NO OTHER winery can offer: Vino Nobile tasting inside an authentic 6th-century BC Etruscan tomb. Archaeology + enology = unforgettable and world-unique experience.

✨ Luteraia - Dreamlike tastings
Sensory experience where wine is tasted in an atmosphere designed to enhance every nuance. Lights, sounds, temperature, everything calibrated for a tasting experience beyond the glass.

Contact us to book these exclusive experiences.
The Wine Triangle can become even more special.

PRACTICAL INFO

📍 DISTANCES AND TIMES

• Podere → Montepulciano: 40 min (35 km)

  - Podere → Pienza: 35 min (30 km)

  - Podere → Montalcino: 1h (45 km)

  - Montepulciano → Pienza: 15 min

  - Pienza → Montalcino: 30 min

⏰ WHEN TO GO

• Year-round: Villages and wineries open 12 months

  - High season: Spring (April-June) and fall (September-October) - harvest period, spectacular colors, perfect climate

  - Low season: Winter - fewer tourists, authentic atmosphere, quieter tastings

  - Events: Fiera del Cacio Pienza (first Sunday September), Benvenuto Brunello (February), Jazz&Wine Montalcino (July)

💡 USEFUL TIPS

• - Winery reservations: Always recommended, mandatory weekends and high season

  - Designated driver: Necessary - tastings are serious

  - Minimum time: 2 days to experience everything leisurely, 1 intensive day doable but rushed

  - Tasting budget: €15-25 historic cellar, €35-50 premium winery with tour, €60-80 dinner with wine pairings

  - Shopping: Bring cooler bag for pecorino and wines (especially summer)

Ready for the ultimate food and wine journey?

Start from Podere Grotta Antica and discover the Wine Triangle

Two days among historic cellars, UNESCO villages and legendary flavors. Vino Nobile, Brunello, pecorino in barriques. The excellences that made Tuscany world-famous await you less than an hour from Podere.

Book your stay and let us guide you through authentic wine Tuscany.