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Our most recommended Pienza Tours

From Rome: Tuscany Guided Day Trip with Lunch & Wine Tasting

1. From Rome: Tuscany Guided Day Trip with Lunch & 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.

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

2. 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.

Montepulciano & Pienza: Wine Tour From Florence

3. Montepulciano & Pienza: Wine Tour From Florence

Leave the bustling Renaissance hub behind as you travel comfortably in an air-conditioned vehicle to the enchanting locales of Pienza and Montepulciano. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Delight your taste buds with the exquisite flavors of the renowned Brunello di Montalcino wines. Plunge into the picturesque village of Montepulciano nestled in the Val d’Orcia, where you'll be captivated by the elegant Renaissance architecture and the breathtaking vineyard landscapes. Enjoy some leisure time to explore the village at your own pace. Reach finally Pienza, where you'll conclude your journey in the Renaissance era. Admire the panoramic vistas of the surrounding Val d’Orcia while diving into the rich history and enduring traditions of Pienza. At the end of your trip, enjoy your comfortable back to Florence.

From Siena: Montepulciano & Pienza Wine Tour

4. From Siena: Montepulciano & Pienza Wine Tour

Enjoy a day of culture, wine, and food as you visit some of the most impressive towns and villages in Tuscany. Meet your guide in Siena and join the rest of the group to start your full-day tour. Explore Montepulciano, where the stateliness of its Renaissance buildings and the refined beauty of the town's churches mix with the ancient tradition of winemaking. Cross gently rolling hills full of vineyards, and then sample local wines served with some snacks. Enjoy some free time in this magnificent village. 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. Enjoy the end of the tour by walking through the streets of the village before your return transfer to Siena by bus.

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 farm. 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, tour one of the many wineries carved out of the earth below the city and discover some of the palaces of the noble families that once lived here. Taste the Vino Nobile local wine and 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!

Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano

6. Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano

The tour departs from Florence and heads into the luscious surrounds of Val d’Orcia, a UNESCO World Heritage Listed site since 2004. As you travel to the first destination of the day, feel immersed in the region’s breathtaking landscapes, which were a source of inspiration for many Renaissance painters. Arrive at Montalcino, a locally owned family-run winery with an immensely welcoming atmosphere. Settle into the winery as if you were at home and learn everything there is to know about Brunello di Montalcino wine, vineyard techniques, the wine making process, wine aging, and how to appreciate wine properly. Enjoy a tasting session of the winery’s wines and try to pick up the flavors that are unique to this region. After the wine tasting, head to the nearby Papal village of Pienza, famous for its delicious Pecorino cheese. Here, enjoy a gourmet 3-course lunch in the colorful gardens of a former convent that dates back to the 15th century (April to October only). In winter season, lunch will be served inside at the restaurant). Following lunch, spend some free time exploring the town, wander around its historic center, and visit the famous cheese shops to pick up a tasty souvenir. Continue onto Montepulciano next, the final stop of the tour. Famous worldwide for its Vino Nobile wine, Montepulciano is a quintessential medieval Tuscan village with vast green landscapes marked by rolling hills and castle walls. Follow your guide for a tour of the village’s historical cellar, known locally as the ‘underground city’ and then enjoy another wine tasting session along with a sampling of delicious olive oils and other food specialties. At the end of the tasting there’s enough time to visit the main square to take some photos of the breathtaking landscape before returning to Florence.

Pienza: Dairy Farm Tour with Pecorino Cheese Tasting

7. Pienza: Dairy Farm Tour with Pecorino Cheese Tasting

This tour will take you to discover one of the best Tuscan products, right at a dairy farm located in the beautiful hills of the Val d'Orcia (UNESCO World Heritage Site). Here, you will observe the techniques of cheese processing, meeting these artisans of flavors, understanding the differences between the various types of Pecorino cheese, and finally you will learn to taste it. Flocks of sheep graze on the Val d’Orcia hills, feeding on the herbs offered by this area: the result is a high-quality milk, which, once it is processed, turns into the famous Pecorino cheese, with its unmistakable flavor. Be it fresh, semi-seasoned, or seasoned, you will realize that Pecorino cheese from Pienza is excellent in every version, pure or paired with honey or jams.

Florence: Orcia Valley, Montalcino, Pienza with Lunch & Wine

8. Florence: Orcia Valley, Montalcino, Pienza with Lunch & Wine

Discover the medieval villages of Tuscany on this full-day guided tour from Florence. Browse the historic center of Pienza and the fortress of Montalcino. Enjoy a gourmet lunch and three wine tastings at the Temple of Brunello. Explore the Sant'Antimo Abbey with an audio guide and the Palazzo Pubblico. Start the tour in Pienza with free time to explore the first ideal city of the Renaissance. Tour the historic center from Piazza Pio II, the Duomo of Santa Maria Assunta, and Palazzo Piccolomini. If you select the option for the Palazzo Pubblico, enter the former residence of the Priors. Head to Montalcino, a perfectly preserved medieval town with a massive fortress. Start in the former convent of Sant’Agostino, which now houses the Temple of Brunello interactive museum. Travel through local history and culture to discover the production of the renowned Brunello di Montalcino wine. Top off the visit with a tasting of the famous Tuscan Brunello and lunch in the cloister of the Temple of Brunello. Let the chef’s creativity inspire you as the explosion of flavors perfectly combines with the richness of the best Tuscan wines. Close your adventure with a visit to Sant’Antimo Abbey, a Benedictine church founded, according to legend, by Charlemagne in the ninth century. See the scenic clearing surrounded by wheat fields, ancient olive trees, and vineyards. Raise a final glass to the day’s adventures before returning to Florence.

From Rome: Private Day-Tour of Tuscany

9. From Rome: Private Day-Tour of Tuscany

"Escape to Tuscany: Montepulciano, Pienza, and Tuscan Vineyards from Rome" Leave behind the bustling cityscape of Rome for the tranquil charm of Tuscany on this scenic excursion. Your adventure kicks off with a convenient pick-up in Rome via a comfortable air-conditioned car or minivan. By mid-morning, arrive at the ancient Etruscan town of Montepulciano. Dive into the underground wine cellars, home to the acclaimed Nobile wine, and savor a delightful wine tasting session. Take in breathtaking vistas of Tuscany’s lush vineyards before your private driver escorts you to Montepulciano where you can visit parts of the Old underground city and Etruscan thumb. Pause at Pienza, where you'll have free time for a leisurely lunch. Gain insight into notable attractions like the two Renaissance palaces and the exquisite Duomo to explore during your time in town. Pienza’s quaint size encourages self-guided exploration, allowing you to immerse yourself in its historic architecture and panoramic countryside views. Don't miss sampling Pienza's famed specialty, pecorino cheese, available at various artisanal food stores dotted around the town. With your bags brimming with wine and cheese, reconvene at the vehicle for a comfortable and picturesque return journey to Rome.

Pienza: Guided E-bike Tour through the Val d'Orcia

10. Pienza: Guided E-bike Tour through the Val d'Orcia

Our e-bike tour through the Val d'Orcia also includes visits to some of the region's most iconic landmarks, including the 500-year-old Giardino in San Quirico. This stunning garden is a true masterpiece of Italian design and is sure to take your breath away. Another highlight of the tour is the visit to the Chapel of Vitaleta, a beautiful stone chapel that stands in a picturesque countryside setting. This iconic landmark has been featured in many postcards and photographs, and its beauty is truly awe-inspiring. As you continue your journey through the Val d'Orcia, you'll also have the chance to explore the Campi Elisi the most breathtaking and iconic landscapes in the region. These stunning fields are filled with colorful wildflowers, and their beauty is unmatched by anything else in the world. With our expert guide leading the way, you'll have the chance to discover all of these amazing landmarks and more during your e-bike tour through the Val d'Orcia. If you're looking for other guided tours in the area, don't worry. In addition to Pienza, you can find similar experiences in Cortona, Arezzo, Castiglion Fiorentino, and Montepulciano. And if you desire a personalized experience, simply contact us, and we'll create a tailor-made tour just for you. Don't miss the opportunity to have a unique and unforgettable experience in beautiful Tuscany!

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What people are saying about Pienza

Melissa was absolutely pleasure, she was knowledgeable and fun! An organized tour that felt comprehensive. Unfortunately we went on a very foggy day and we weren’t able to see the full Tuscan landscape but she made the experience as enjoyable as it can be given the circumstances. Pur local tour guide in montepulciano Chiara was charming. Lets not forget the driver! Julio! Fantastic navigation skills. I’m prone to motion sickness but he did well!

I took my wife, 2 boys 13 and 11, my mother, and my in-laws and they all really enjoyed the trip. The weather wasn’t the best but Tuscany was still very beautiful, lunch was great, the guide was very patient and knowledgeable, and the driver got us there without incident. All of my family members stated that they had a very good time.

It was very nice trip, I enjoyed. Our guide Marylin and the driver Andrea both are elevated Our day with lots of fun and joy. Marylin's explanation about the rome history is very clear and understandable. Many thanks for you guys giving us the opportunity to taste the fresh olive oil and wine. The lunch was awesome. Thank you.

The tour was incredible! The guide Paula was super friendly and asked for information about the tour and the city of Rome, she exceeded my expectations.

What I've enjoyed the most was the time witb the other people at lunch...great time. But in general, all was fantastic.