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Tuscan Hills Full-day Tour: Val D’orcia, Montalcino, Montepulciano & Pienza With 2 Wine & Cheese Tastings

Piazzale Montelungo, FI Firenze

Escape the hustle and bustle of Florence and discover the heart of Tuscany on a tour through the enchanting Val d’Orcia, a UNESCO World Heritage Site.

Cancellation policy

Review the supplier policy below before booking.

Duration 11h 30m

Duration supplied by the experience provider.

Languages

English, Italian, Spanish

Group size

1–20 travelers

Full description

Escape the hustle and bustle of Florence and discover the heart of Tuscany on a tour through the enchanting Val d’Orcia, a UNESCO World Heritage Site.
Visit the charming towns of Montalcino, Pienza, and Montepulciano while enjoying two wine and pecorino cheese tastings!

The tour begins in Montalcino, home of the world-famous Brunello Wine, where a unique wine cellar will captivate you with its charm. Wander through the town’s picturesque streets to the top, where breathtaking views await: golden hills, ancient oaks, scenic olive groves, winding country roads through perfect vineyards, and solitary cypress trees. Keep your camera ready!

Next, explore Pienza, the “ideal city” of the 15th century designed by Bernardo Rossellino for Pope Pius II. Admire architectural treasures such as the Duomo and Palazzo Piccolomini, featured in Zeffirelli’s Romeo and Juliet, and enjoy one of the most beautiful panoramic views of Val d’Orcia.

Finally, visit Montepulciano, famed for its Vino Nobile vineyards and its cinematic history. Savor a final wine and pecorino tasting inside a historic underground cellar before returning to Florence.

Itinerary

Florence - Piazzale Montelungo

Pienza. The first stop of the day is the town of Pienza, around one hour and a half from Florence. Enjoy some free time to explore the first “ideal city” of the Renaissance period that dominates the valley from up above, giving you an incomparable sight of the surrounding hills. Start the tour from the heart of the historic center: Piazza Pio II with its honey-colored buildings, the Duomo of Santa Maria Assunta, and Palazzo Piccolomini.

Montalcino. Then you will head to Montalcino, the Medieval town par excellence dominated by its massive fortress. In just about thirty minutes you will reach the hometown of Brunello and you will have some free time to explore the most authentic borgo of Val d’Orcia. Breathe in the peaceful atmosphere and step back to the past while taking a stroll down its steep alleys. Think about having a coffee in Piazza del Popolo to recharge your batteries before visiting the Temple of Brunello. 

Montepulciano. Next up is a unique experience inside the monumental complex of the former convent of Sant’Agostino, which now houses the Temple of Brunello: an interactive museum where you can unveil the secrets of Montalcino's famous red wine and its hometown through an immersive path. Start a multi-sensory journey through local history and culture to discover the pillars of the production of one of the most renowned wines of Italy, Brunello di Montalcino. But that’s not all! Top off the visit tasting the famous Tuscan Brunello to finally understand why it's addressed as the King of Sangiovese wines. You will find waiting for you in the cloister of the Temple a sumptuously laid table, so get ready to taste a delicious lunch made of gourmet dishes accurately paired with three glasses of local wine. Let the chef’s creativity inspire you as the explosion of flavors perfectly combines with the richness of the best Tuscan wines.

What’s included

Included

  • Roundtrip journey by fully-fitted GT Coach
  • Expert multilingual escort
  • Free visit of Montalcino, Pienza and Montepulciano
  • Visit to a wine cellar in Montalcino with tour of the wine cellars and tasting of the world-famous Brunello
  • Visit to a winery in Montepulciano with tasting of the “Vino Nobile”
  • Pienza'pecorino cheese tasting
  • Possibility of buying wine and cheese at a very competitive price
  • Possibility to retrace the Gladiator's Walk

Not included

  • Food and drinks, unless specified
  • Gratuities
  • Hotel pickup and drop-off

Important information

Meeting point

Piazzale Montelungo, FI Firenze

Don’t forget

Comfortable shoes are recommendedPlease note that the given order of the visits may changeWe regret to inform that this tour is not suitable for guests with wheelchairs or with impaired mobilityEnglish and Spanish are always guaranteed. In order to confirm the excursion in Italian, German, Portuguese or French a minimum of 4 pax is required Comfortable shoes are recommended

Cancellation policy

100% charge if cancelled within 48 hours of start.

Your host

VE

Verified Local Host

With GetExperience since 2026

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