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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.

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!

From Siena: Val D'Orcia Wine Tour

3. 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

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.

Florence: Val d'Orcia Private Chauffeur-Driven Tour

5. 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: Val D'Orcia, Montepulciano, Pienza Wine Tour

6. 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 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.

From Rome: Private Day-Tour of Tuscany

7. 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.

Pienza: Palazzo Piccolomini & Palazzo Borgia Entrance Ticket

8. Pienza: Palazzo Piccolomini & Palazzo Borgia Entrance Ticket

A visit with the audioguide allows you to discover the inner courtyard of this wonderful palace, built as an expression of the interrelations between man and nature. Wander through the hanging garden and the charming rooms of the Palazzo Piccolomini and the Palazzo Borgia, then enjoy a breathtaking view from the loggia over the Orcia Valley.  Palazzo Piccolomini was the summer residence of Pope Pius II, and is part of a complex that includes the cathedral and the square, commissioned by the Pope and built in 1459 by famed architect Bernardo Rossellino, student of Leon Battista Alberti. The rooms on the main floor are furnished with period furniture, paintings and other furnishings, testimony to a past that still remains intact. Part of the Bishop’s Palace together with the palace of Cardinal Francesco Jouffroy of Arras, Palazzo Borgia, once owned by Cardinal Rodrigo, future Pope Alexander VI, overlooks the square. Pienza is also known as having the first roof garden of the Renaissance, with views of the Val d'Orcia and Mount Amiata.

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).

Arezzo and Province: Drive Vintage Vehicle with Audio Guide

10. Arezzo and Province: Drive Vintage Vehicle with Audio Guide

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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What people are saying about Pienza

Overall rating

4.5 / 5

based on 1,167 reviews

Ana, Francesca and Julio made our day! Ana shared interesting facts and told us everything we needed to know without making it boring and also threw in some jokes. We went on a really cold day, but she made it shine with her vibe. Francesca was so cute! She showed us around and made walking up & down the hills a lot easier than it seemed. Unfortunately at the last stop everything was closed (cold weather and February), but there were still really beautiful views :) Overall we enjoyed it very much, wine was amazing, food was even better and everyone was really welcoming. Recommend 100%, but probably better with warm weather.

Me and my wife had a really good time and we got to see so many interesting places that we wouldn’t have found by our self’s. Elizabeth, Tabata and Paulo the driver did a really good job. Highly recommend!

The tours were very informative and interesting. They start earlier than the first destination, so try and sit towards the front of the bus.

The trip was perfect. Peter the driver was kind, nice and it was a very pleasant experience. I will definitely be back

Beautiful trip. I enjoyed every single minute of it