Our hill town hopping adventure through Pienza, Monticchiello, and Montepulciano was straight out of a Tuscan daydream – and easily one of the coziest, cheesiest, and cat-filled days of our 2016 Italy trip. We started in Pienza, a town known as the first true expression of Renaissance Humanist urban design (because even in the 1400s, Italians had strong opinions about layout). We wandered the charming Piazza Pio II, peeked into Piccolomini Palace, and, of course, sampled the town’s famous pecorino cheese. From there, we made our way to Monticchiello, where the views at Osteria La Porta made us feel like we’d accidentally wandered into an Italian Olive Garden commercial – except with actual wine and charm. Finally, we rolled into Montepulciano, met a very cuddly street cat we named Monte, and explored the town’s wine scene – starting with Contucci Cantina, a medieval cellar straight out of a movie. We headed straight into the atmospheric depths, where we met Adamo, the legendary and endlessly friendly vintner featured in Rick Steves’ videos. Wandering past enormous casks of wine tucked under ancient stone arches made us feel like we’d unlocked a hidden level of Tuscany. We wrapped up the day back at our 12th-century agriturismo, Castello di Spedaletto, a working castle with a real mill and the kind of peaceful countryside charm that makes you wonder if maybe this is where you were meant to live all along.

Itinerary

This itinerary highlights our visits to the Tuscan hill towns of Pienza, Monticchiello, and Montepulciano during our 2016 Italy trip (September 4).

• 🚗 Drive (13-min) to Pienza and explore Renaissance urban design
  • ⛪️ Piazza Pio II
  • 🏰 Piccolomini Palace
  • 🧀 Try pecorino cheese
• 🚗 Drive (14-min) to Monticchiello and explore
  • 🍷 Wine and/or lunch from Osteria La Porta (gorgeous views)
• 🚗 Drive (15-min) to Montepulciano and explore
• 🍝 Lunch at Caffe Poliziano (stunning views)
• 🍷 Visit wineries in Montepulciano hill town
  • Contucci Cantina (9:30 AM – 12:30 PM, 2:30 PM – 6:30 PM, skip tasting room and head to the medieval cellar to meet the friendly, vintner – Adamo)
  • La Citta Sotterranea (8 AM – 10 PM, free “The Underground City” tour of extensive underground caves and cellars with a free wine-tasting afterwards)
  • De’Ricci Cantine Storiche (10:30 AM – 7 PM, free tasting, historic wine cellar dating back to 1150)
• 🍷 Visit other wineries outside of town (time permitting)
  • Fattoria della Talosa (nice cellars with big barrels, 6-min outside town)
  • Tenuta Valdipiatta (🎟️ Winemaking class offered, 11-min outside town)
  • Boscarelli (🎟️ Reservation required, personal tours offered, 12-min outside town)
  • Salcheto (beautiful views, eco/sustainable winery, 16-min outside town)
  • Avignonesi (30-min out town)
• 🍽️ Dinner at La Bottega del Nobile
• ♨️ Optional: Hot springs
• 🏰 Return to Castello di Spedaletto

Pienza

Hill town

Perched atop a hill in Tuscany’s Val d’Orcia, Pienza is celebrated as the “ideal city” of the Renaissance. Originally a modest village named Corsignano, it was transformed in the 15th century by its native son, Pope Pius II, who envisioned and implemented a harmonious urban design under the guidance of architect Bernardo Rossellino. This ambitious project introduced a rational layout and elegant architecture that have endured through the centuries. In recognition of its historical and cultural significance, Pienza’s historic center was designated a UNESCO World Heritage Site in 1996.  Beyond its architectural allure, the town is also renowned for its production of pecorino cheese, offering visitors a delightful blend of cultural and culinary experiences. 

Castello di Spedaletto

Nestled in Tuscany’s Val d’Orcia, the Castello di Spedaletto is a remarkable 12th-century fortress originally established by Ugolino da Rocchione along the historic Via Francigena to shelter pilgrims journeying to Rome. The castle’s architecture features a square layout with corner towers, crenelated battlements, and a fortified entrance crowned by a commanding keep. Notable historical figures, including Charles II of Anjou and Pope Pius II, are recorded to have stayed within its walls.  Today, Castello di Spedaletto has been thoughtfully restored and transformed into an agriturismo, offering guests a unique opportunity to experience its rich history amidst the serene Tuscan landscape. 

Monticchiello

Nestled in Tuscany’s Val d’Orcia, Monticchiello is a charming medieval village known for its well-preserved stone walls, cobblestone streets, and breathtaking views of rolling hills and cypress-lined roads.  This tranquil hamlet offers visitors a glimpse into authentic Tuscan life, away from the bustling tourist paths.

Montepulciano

Hill town

Perched on a ridge in southern Tuscany, Montepulciano is a picturesque medieval hill town known for its Renaissance architecture, sweeping views, and world-famous Vino Nobile di Montepulciano wine. Its charming streets are lined with historic palaces, churches, wine cellars carved into the hillsides, and the lively Piazza Grande at its heart. Montepulciano blends rich history, local flavor, and scenic beauty – making it a must-stop for wine lovers and Tuscan daydreamers alike.

Contucci Cantina

The Contucci family dates back to the 11th century and is known for its long history of winemaking, cultivating vines even before the Renaissance and contributing to the fame of Vino Nobile di Montepulciano. We headed straight to the cellar and met Adamo, the friendly, vintner featured in Rick Steves’ videos.

De’Ricci Cantine Storiche

De’ Ricci Cantine Storiche is a breathtaking wine cellar known as the “Wine Cathedral” for its grand, cathedral-like architecture of arches and columns. Built atop ancient Etruscan caves and dating back to the 1300s, the cellar sits beneath the Renaissance-era Palazzo Ricci and offers visitors a chance to explore its historic depths while tasting Vino Nobile di Montepulciano produced using sustainable methods.

La Citta Sotterranea

Beneath Montepulciano’s historic center lies this underground city, stretching beneath noble palaces with stone tunnels, ancient wells, Etruscan tombs, and massive wine barrels aging Vino Nobile di Montepulciano and vinsanto DOC. Along the route, you’ll find cellars, fountains, and even a quirky collection of museums curated by the Ercolani family – featuring everything from fossils and viticulture tools to old torture instruments. It’s a fascinating mix of history, mystery, and wine all beneath the city streets.

Caffé Poliziano

Caffè Poliziano is a historic café established in 1868 and known for its elegant Art Nouveau interior and sweeping views over the Val di Chiana. Once a favorite of literary and artistic figures like Carducci and Fellini, it now serves as both a cultural landmark and a spot to enjoy Tuscan cuisine, espresso, and local wines, all with a side of timeless charm.