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Things to do in Pienza

Our most recommended things to do in Pienza

From Rome: Tuscany Day Trip with Lunch and Wine Tasting

1. 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.

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.

From Florence: Val D'Orcia, Montepulciano, Pienza Wine Tour

3. From Florence: Val D'Orcia, Montepulciano, Pienza 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 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. Next, go to Pienza to explore its Renaissance heart. Enjoy panoramic views of the surrounding Val d’Orcia, and learn about Pienza’s ancient traditions before your return transfer to Florence.

From Siena: Val D'Orcia Wine Tour

4. 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. 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 a delicious snack of the local produce. 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 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.

Florence: Val d'Orcia Private Chauffeur-Driven Tour

7. 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.

Day Trip From Rome: Tuscan Hilltowns, Fortresses & Vineyards

8. Day Trip From Rome: Tuscan Hilltowns, Fortresses & Vineyards

Experience a unique side of Tuscany on a small-group tour and visit areas that aren't accessible to larger vehicles. Explore a family-run farm and dine on a terrace overlooking Val d’Orcia, climb the walls of Montalcino castle, shop in Pienza, and sample some good wine at a local vineyard. Your tour starts early, whisking you from Rome in an air-conditioned luxury minibus that takes you straight into the heart of Tuscany. Your first stop is at Pienza, where your expert tour leader gives you an introduction to the history of the town, famous for its Pecorino cheese. Next, you get some free time to explore, and take the chance to do some shopping if you like. See the advantage of traveling in a small vehicle as you navigate the narrow route to a family-run organic farm. Learn about the local life, including how the farmers make their own olive oil and cheese, before you enjoy a mouthwatering lunch with ingredients that were grown onsite. The menu changes daily, with plenty of wine, olive oil, and cheese for a perfect reflection of traditional Tuscan living. Later, stop at Montalcino Castle and climb the walls for stunning views of Tuscany. Hear about the area's history and its main highlights before you move onto the last stop of the day, a Montalcino vineyard. Enjoy a tour of the cellars before a tasting of the region's world-famous wines.

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

9. 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. 

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.

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What people are saying about Pienza

Overall rating

4.5 / 5

based on 1,185 reviews

From the beginning of the trip the tour guide Valentina was very welcoming and ensured her guests were treated with the upmost respect. Valentina was very knowledgeable from the history of certain areas of our trip to her recommendations for food and sites to see after the tour. The overall experience of the locations visited we’re breathtaking. The additional tour guides were also welcoming and informative. If I were to visit Rome again I would highly book another trip with this company to ensure I get the best experience during my time in Italy.

So much fun with our guide Heather and driver Andre. They looked after us very well all day long. The views were amazing and overall the day was very enjoyable, made several friends on the trip as a solo traveler so never really felt alone. Would recommend!

Anna (guide) and Andrei (driver) were both excellent and made the trip a breeze for all patrons. My girlfriend gets motion sick easily and they offered her the emergency seat in the front of the bus to alleviate it. Highly recommended.

The mountaintop town and the farm were the best! Fantastic views and great homeade food!

Heather is the best guide! Thanks for a wonderful honeymoon excursion to Toscana