Pienza
Nature & Adventure

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Our most recommended Pienza Nature & Adventure

Pienza and Montepulciano Wine Tour from Siena

1. Pienza and Montepulciano Wine Tour from Siena

Enjoy a day of culture, wine, and food as you visit some of the most impressive towns and villages in Tuscany. Go to the picturesque town of Pienza, and taste world-famous wines produced in Montalcino and Montepulciano. Meet your guide in Siena and join the rest of the group to start your full-day tour. Depart Siena and transfer to a wine cellar in Montalcino. Cross gently rolling hills full of vineyards, and then sample local wines served with a delicious snack of the local produce. Continue to Pienza to discover the “Touchstone of Renaissance Urbanism.” Considered an artistic jewel of the landscape of Val d’Orcia, Pienza is a perfect combination of architectural beauty and harmony. Most of the lanes bearing impressive names overlook the breathtaking landscape of the Val d’Orcia. Unique smells and flavors are entwined with this natural and artistic heritage. Pienza’s most renowned tradition is pecorino cheese. End the tour at Montepulciano, where the stateliness of its Renaissance buildings and the refined beauty of the town's churches mix with the ancient tradition of wine making. Enjoy some free time before your return transfer to Siena by bus.

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From Siena: Pienza and Montepulciano Small-Group Tour

2. From Siena: Pienza and Montepulciano Small-Group Tour

Travel along one of the most panoramic roads in Tuscany, driving the characteristic moonscape of the Crete Senesi en route to the medieval hamlet of Pienza in the Val D’Orcia valley. One of the first towns to be entirely planned on paper by important architects and artists of the time, Pienza was commissioned by Pope Pius II - the humanist pope - to help him renovate his native town and bring it to new splendor. A wholesome lunch, based on fresh local ingredients will be waiting on a beautiful terrace (weather permitting) at a local dairy farm. Learn about the process of making Italy’s famous pecorino cheese. Continue in the afternoon to Montepulciano, one of Tuscany’s largest hill towns. Under the dominance of Siena in the Middle Ages, and Florence during the Renaissance, today it is renowned for its wine. See influences from both towns in the architecture and art of the historic center, located on a steep hill with beautiful views of the Tuscan and Umbrian border. Go to the main Piazza Grande, and tour one of the many wineries, carved out of the earth below the city. Discover some of the palaces of the noble families that once lived here. After a short walk around town with a guide, enjoy some free time to taste the fabled wines, or continue to explore the palaces, churches and streets on your own. As you follow the route of the main road downhill, imagine how hard the “Bravio delle Botti” festival must be; a competition to race wine barrels from the bottom to the top of the hill!

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From Rome: Full-Day Trip to Tuscany

3. From Rome: Full-Day Trip to Tuscany

During this tour around Tuscany you'll see the medieval architecture of towns such as Montepulciano, Pienza, Monteriggioni and Siena. You’ll see the winemaking process, have a chance to taste some of the region’s fine wines and enjoy a lunch of tasty regional specialties. The town of Montepulciano was a crucial trading center for Tuscany from the Middle Ages through the Renaissance. Its fame today derives from its world-renowned red wine. Proceed to the town of Montalcino, which has always been of major importance to the region due to its strategic hilltop position. It is home to Brunello, the well-known Tuscan red wine. Brunello is produced exclusively from the Sangiovese Grosso grape. The country’s average annual production is nearly 8 million bottles. Next on your tour is a stop in Siena, where you’ll see the medieval towers and alleyways that characterize this elegant town. The Piazza del Campo, the shell-shaped main town square, is one of the most unique in Italy. This is the home to the famous horse race known as the Palio one of the country’s best-preserved medieval traditions.

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Florence: Wine Tasting and Tuscan Villages Full-Day Trip

4. Florence: Wine Tasting and Tuscan Villages Full-Day Trip

Discover the magical essence of lesser-known Tuscan villages on this trip. Immerse yourself in rural culture and authentic beauty of Val d’Orcia valley. Relax while tasting local wine and experience the scenic panoramas and rolling vineyard-covered hills of the region.  Listen to the history of hidden villages from your guide. The harmonious hills of this magical place change colors every season. Feast on a traditional Tuscan lunch. Taste their wines paired with local cheese and extra-virgin olive oil. After lunch, continue to your next stop. Relax in the famous Roman spa of Bagno Vignoni. The hot and steaming thermal waters are great for sore muscles. Rejuvenated, continue to Pienza, an incredible village full of history and traditions. This town is famous for its typical cheese, the “pecorino”. See excellent examples of Renaissance architecture in the historic center.

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Arezzo and Province: Guided Tour by Driving Vintage Vehicle

5. Arezzo and Province: Guided Tour by Driving Vintage Vehicle

This tour is designed to familiarize you with places of historical and nostalgic significance. Many of the places available to discover on this tour are off-the-beaten path, and not commonly seen by tourists.  Start your adventure at the meeting point where you will get to choose your tour option, and the vintage vehicle you desire to drive. Pick the tour most suited to your needs and the car you've always dreamed of driving. Once you've picked your tour and vehicle, you will be required to successfully complete a driving lesson to familiarize yourself with the technical components of driving your vintage vehicle.  Once you have learnt the basics, you will be able to set-off, learning a lot about the places you drive past with your complimentary audio-guide. Your vehicle will be equipped with everything you need as you drive through quaint Tuscan towns and witnessing places of historical curiosity.

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Tuscany: Movie Sets Tour in Valdichiana Senese & Val d'Orcia

6. Tuscany: Movie Sets Tour in Valdichiana Senese & Val d'Orcia

Explore the cinematic side of Tuscany on this guided movie set tour that visits iconic film locations in Valdichiana Senese and Val d'Orcia. See where films like “The Gladiator” and “The Twilight Saga: New Moon” were filmed. Afterward, enjoy a wine tasting at an underground cellar in Montepulciano. Begin at the meeting point in Piazza Grande, Montepulciano. From there, visit the villages and hills between Valdichiana and Val d’Orcia that have been featured in your favorite films. “The Gladiator,” “The Twilight Saga: New Moon,” “The English Patient,” “Midsummer Night’s Dream,” “Heaven,” “Under the Tuscan Sun,” and “The Medici” are some of the major film sets you may recognize. Listen as your guide retraces the plots of the moments shot at these locations. At the end of the tour, enjoy a wine tasting of Vino Nobile di Montepulciano DOCG at an underground cellar in the historic center of Montepulciano. Tour the cellar as you sip your wine.

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Pienza with Cheese and Wine Tasting: Full-Day from Rome

7. Pienza with Cheese and Wine Tasting: Full-Day from Rome

Meet with your private driver and depart towards the Southern part of Tuscany. Here you will visit Pienza, a real Renaissance pearl. Breath in the landscape and scenery and feel the history of the area. Next you will reach Giuseppe's farm, where you will gain a real feeling of nostalgia for the ancient art of sheep's cheese production. Let your tastebuds run wild with the delicious flavors.  The second part of the tour is spent exploring the town of Pienza itself. Walk through the streets, and visit the most important parts of town. Pienza is now known for its wine production and food culture. In particular, Pienza is famous for its pecorino cheese, that is matured in several different ways in order to enhance its flavor. At the end of the tour, sit back, relax and enjoy your 2.5-hour drive back to your hotel in Rome. The duration of your tour is about 10 hours and you can expect to be back at your hotel around 18:00, depending on local traffic. 

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Florence: Val d'Orcia Private Chauffeur-Driven Tour

8. Florence: Val d'Orcia Private Chauffeur-Driven Tour

Let your driver do all the work as they take you on a journey through the enchanting Val D'Orcia countryside, a region known for its scenic beauty, picturesque villages, rolling hills, and cypress trees. Explore in total freedom the enchanting towns of Montalcino, Pienza, and Montepulciano, and try some of the best wines in the world. The first stop will be Montalcino, the land of the world-renowned Brunello wine. Here you will be enchanted by the outstanding charm of the tiny village itself, a maze of cobbled streets, quaint wine shops, and Romanesque-style churches. Next stop is the majestic medieval fortress. Admire the views of sunny rolling hills, picturesque olive groves, and scenic country roads winding through perfect vineyards. Continue to Pienza, built high on a hill with extraordinary views of the Orcia valley. The entire city was rebuilt as an ideal Renaissance town by order of Pope Pius II, and represents the first application of humanist urban planning concepts. Explore the pretty alleyways of this small town at your leisure and soak up the relaxed atmosphere. The last stop will be Montepulciano, home to the famous Vino Nobile vineyards and more recently famous for the filming of the vampire movie "New Moon". Enjoy free time here to stroll around Renaissance buildings, majestic palaces, and imposing churches.

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Tuscany: Full-Day Wine Tour with Tastings

9. Tuscany: Full-Day Wine Tour with Tastings

Begin your wine tour with a pickup from your accommodation and head to your first winery in Brunello. Once there you will enjoy samples of Brunella, Riserva, and Supertuscan wines at this historic winery. Following that, head to the second winery and learn about the family-run establishment including exactly what makes it one of the most famous wineries in the area.  Take a break from wine and continue on to Pienza. Referred to as the "pearl of Valdorcia", Pienza is known for pecorino cheese. You'll also visit the city center and take a scenic walk, with the opportunity to visit local boutiques for a quick cheese tastings at your disposal. You'll later end your wine tour with a visit to the village of Montepulciano. There you will make your way underground to a wine cellar enjoy a delicious lunch consisting of typical Tuscan products,paired with Nobile di Montepulciano wines. Following your lunch, you'll return back to your accommodation.

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Other Sightseeing Options in Pienza

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What people are saying about Pienza

Overall rating

4.6 / 5

based on 124 reviews

I can't say enough about my guide, Marzia - she is a total 5-star guide and went above and beyond to make my trip incredible!! She is also super knowledgeable about the history and culture of Italy and Tuscany, you can ask her anything from Italian history, Tuscan history, Tuscan wine to the tree on the road! Marzia also holds a environmental guide license she is really the greatest guide you could meet!

It was a great experience discovering wonderful places. The guide was thorough and kind. I recommend the tour to those who do not have a car and want to visit more places in a short time. We came back tired but happy.

Excellent wine tasting in Montalcino!!!! Lucia’s knowledge of wine and history was enlightening!!! Best tasting ever.

The activity was what we wanted. Alexander the driver speaks very good spanish and he helped us all the time.

Highlight of our trip Georgia was knowledgeable and entertains and a perfect host and teacher.