Pienza Wine tasting & winery tours

Our most recommended Pienza Wine tasting & winery tours

From Siena: Val D'Orcia Wine Tour

1. From Siena: Val D'Orcia Wine Tour

Enjoy a day of culture, wine, and food as you visit some of the most impressive towns and villages in Tuscany. See 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 winemaking. Enjoy some free time before your return transfer to Siena by bus.

From Rome: Tuscany Day Trip with Lunch and Wine Tasting

2. From Rome: Tuscany Day Trip with Lunch and Wine Tasting

Leave Rome's hustle and bustle behind and head to Tuscany for the day.Enjoy a guided town of Montepulciano and eat a delicious 3-course lunch with an Italian wine-tasting experience you won't forget. A comfortable, air-conditioned coach will pick you up in Rome. As you drive towards rolling hills, your expert tour guide will explain Tuscany’s rich culture and answer any questions you might have about the day ahead.  First, enjoy a walking tour of the hill town of Montepulciano. Take in an ancient but still-functioning wine cellar and ruins that pre-date Rome. Next, visit San Biagio, a 16th-century Renaissance church with a travertine facade welcoming in the sunlight and exquisite decorations inside. Just a short drive away awaits a delicious Tuscan lunch. Enjoy a 3-course meal with wine pairings in the wine cellar of an authentic vineyard farmhouse, including the famous Brunello di Montalcino and varieties from the vineyard itself.  Buy your souvenir Tuscan wine here, or wait for the final stop: Pienza. Your tour leader will offer insights, but your time is yours: shopping for pecorino cheese, balsamic vinegar, wines, and other local specialties, finding the right photo opportunity, or simply wandering the streets like a local. Next, return to Rome in air-conditioned comfort — fulfilled, relaxed, and ready for the next day.

From Florence: Pienza and Montepulciano Guided Wine Tour

3. From Florence: Pienza and Montepulciano Guided Wine Tour

Explore the wine lands and medieval villages of Tuscany with a guide on a day trip from Florence. Escape the “Cradle of the Renaissance” on an air-conditioned vehicle and head to Pienza and Montepulciano. Sample some of the most celebrated Brunello di Montalcino wines.   Transfer to Pienza to explore its Renaissance heart. Enjoy panoramic views of the surrounding Val d’Orcia, and learn about Pienza’s ancient traditions.  Next, go to the village of Montepulciano in the Val d’Orcia where you'll discover stately Renaissance buildings and churches of rare beauty, all set among the vineyards. Have some free time to visit the village before your return transfer to Florence.

Val D'Orcia: Cheese and Wine Tasting Tour from Florence

4. Val D'Orcia: Cheese and Wine Tasting Tour from Florence

Escape the hustle and bustle of Florence and experience the heart of Tuscany on this day trip from Florence. Ride in a spacious and air-conditioned van to the lush Val D’Orcia, a UNESCO World Heritage site. Stop at wineries, stroll through local towns, and savor local cheese. Hop aboard the comfortable bus at a centrally-located meeting point in Florence. Relax on the drive through the Tuscan countryside on the way to Montalcino. Try some world-renowned Brunello wine and stroll through the cellars and museum of a wine estate. Hear about the history of this estate which once belonged to the powerful Piccolomini family, whose members included Pope Pius II. Move up to the peak of the town for views of rolling hills, ancient oaks, picturesque olive groves, vineyards, and cypress trees. Continue to Pienza, which stands high upon a hill and dominates the Orcia valley with extraordinary views. Explore the charming streets of this small town at your leisure. Head to Montepulciano, home to the famous Vino Nobile vineyards where some of the vampire movie "New Moon" was shot. Sip on some wine while visiting the dungeon where the wine is stored under the ancient walls of the winery. Sample some Pecorino cheese and finally return by bus to Florence.

From Siena: Pienza and Montepulciano Small-Group Tour

5. 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!

From Rome: Private Day-Tour of Tuscany

6. From Rome: Private Day-Tour of Tuscany

Take a break from the chaos of Rome with a Tuscan holiday. The tour focuses on the famous Val D’Orcia region, visiting the historic hill towns of Montepulciano, Pienza, and the vineyards of Tuscany. Be picked up in Rome by a comfortable air-conditioned car or minivan. By mid-morning, you will be in the ancient Etruscan town of Montepulciano. The next stop is at the underground city, where one of Italy’s best wines, Nobile, is produced, and you will indulge in some wine tasting. Absorb views over some of Tuscany’s most beautiful vineyards before your private driver will take you out of town to a beautiful Tuscan vineyard. Stop at Pienza, with some free time for lunch. Get information on sites you may want to visit, such as the two Renaissance palaces and the beautiful Duomo. Pienza is a small town so you’ll go off on your own and take some time to wander around, enjoying ancient architecture and views of the rolling countryside. Whatever you choose to do with your time, be sure to sample Pienza’s most important product, pecorino cheese, in one of the many artisan food stores around the town. With full bags packed with wine and cheese, meet back at the car for a comfortable and scenic drive back to Rome.

Montalcino: Brunello’s Wine Experience and Wine Tasting

7. Montalcino: Brunello’s Wine Experience and Wine Tasting

Pre-book your entry ticket to Brunello Temple for an immersive and emotional journey to discover Brunello, king of wines and of the Montalcino territory. Enrich your visit with an optional tasting of 1 or 2 glasses of Brunello's wine. The experience begins at InChiostro, where a virtual reality viewer station called InVolo will allow you to immerse yourself in villas, castles, vineyards, and the small villages of the vast municipal area. Passing through the uncovered cloister, descend into an underground environment where the four founding pillars that have made Brunello unique are revealed through immersive videos. Move on to hear the voices of Brunello: interviews with the characters who have played a role in Brunello’s legend. In a divine painting, you’ll be invited to leave your mark through the color palette of Montalcino's colors. Artistic masterpieces will be presented in Calix, an expression of the inspiration and creative work that the land of Montalcino has been able to instill in people. Along the route, admire the frescoes of the Church of Sant’Agostino and learn the history of the area and its artistic heritage through the collections of the archaeological museum and the Civic and Diocesan Museum.

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

8. 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.

Florence: Wine Tasting and Tuscan Villages Full-Day Trip

9. 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.

From Rome: Tuscany and Montepulciano Nobile Wine Guided Tour

10. From Rome: Tuscany and Montepulciano Nobile Wine Guided Tour

Board a Wi-Fi equipped Mercedes in Rome and travel to the Montepulciano wine region in Tuscany. Take a tour of a winery and explore the cellars. Taste many types of wine, and snacks. Head to the town of Montepulciano for lunch and visit Pienza. Delve into the Montepulciano wine region of Tuscany as you are picked up at your accommodation. Gaze at the scenery along the way and visit a celebrated winery. Tour the cellars and enjoy a winetasting session. Dine in the town of Montepulciano and continue your tour as you visit medieval Pienza. End your adventure with a transfer back to your hotel in Rome.

  • Entry tickets
  • Guided tours
  • Day trips
  • Private tours
  • Workshops & classes
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