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.

From Siena: Val D'Orcia Wine Tour

2. 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.

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

3. 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

4. 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

5. 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

6. 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.

From Florence: Pienza and Montepulciano Guided Wine Tour

7. 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.

Siena: City Introduction in-App Guide & Audio

8. Siena: City Introduction in-App Guide & Audio

Walk through a beautiful route of the city, discover hidden gems and visit 10+ of the most important attractions and spots. Learn some introductory information about each place and interesting stories about the city in general. Download the ‘World City Trail ‘app from the store and login. Read the instructions and head to the starting location. Unlock photos of the exterior and the interior of the location. Listen or read some information regarding the attraction and continue walking to the next checkpoint. Note what you liked and did not like and create your bucket list for the next days! Start your walk any time, without a schedule. Pause it for lunch, have a drink, visit an attraction of your choice, and continue later or even another day. With the maps feature, you will never get lost. Start your tour from the much-photographed Duomo! Visit the unique Baptistry of St John with its facade still under construction, you will still encounter the famous hill of the imposingness of Palazzo Piccolomini. Take a picture of the small central square Loggia del Papa and let yourself get lost in the Torre del Mangia, which when built was one of the tallest secular towers in medieval Italy. Visit the breathtaking Palazzo Pubblico. You will also pass by the Palazzo Buonsignori with its unique and world-renowned exhibits. Admire the exhibits of Santa Maria della Scala, once an important city hospital dedicated to the care of abandoned children, the poor, the sick and pilgrims. The Facciatone of Siena will fascinate you and your camera with its panoramic view! See, walk and relax in Piazza del Campo, considered one of the largest medieval squares in all of Europe. Known for its beauty and architectural integrity, it will be the icing on the cake of this tour!

Pienza: Dining Experience at a Local's Home

9. Pienza: Dining Experience at a Local's Home

Immerse yourself in a private dining experience at a local's home, enjoying an exclusive cooking show and tasting authentic recipes treasured in family cookbooks passed down by real Italian "Mammas". Feel the warmth of Italian hospitality as you connect with local people. You will enjoy a 4-course menu including a starter, pasta, a main course with a side dish, dessert, and drinks included (water, selection of red and white wines from regional cellars, and coffee).

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

10. 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.

Other Sightseeing Options in Pienza

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What people are saying about Pienza

Overall rating

4.5 / 5

based on 820 reviews

Gabriellie (sp?) was a great tour guide for this day trip to Montepulciano and Pienza. Both locations were spectacular. We also visited a family run restaurant for the wine tasting/lunch and a nearby church, so it was a very full day. There was a quick stop at the start and the end of the tour that provided a chance to have a bathroom break and some shopping or a coffee/snack. It was a full tour bus, so not a small group atmosphere, but still enjoyable. The streets in the towns are narrow and somewhat steep in places which was challenging for some people with mobility issues. Great break from busy Rome.

This was a great day out of Rome. If you want to see Tuscany area and can’t make it while in Florence, this is your tour. 5 star guides with Andrea and Sara. Take this tour as the lunch and wine was excellent.

Anna and Andrea were very helpful during the whole trip and Klaus our guide in Multipulciano was great too! The visit to the restaurant was also great which includes the wine tasting experience !!!

We had an amazing time. Our guide Martha was great. Loved all the visits and the food and wine tasting. Loved the medieval city of Montepulciano. Definitely suggest it

Emiliano is the best guide. If you consider going on this tour ask only for him. You will be entertained, informed and get a lot of good tips for your time in Rome.