Pienza
Wine Tasting & Winery Tours

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Our most recommended Pienza Wine Tasting & Winery Tours

  • Tuscany Taster Tour: Day Trip from Rome with Lunch & Wine

    1. Tuscany Taster Tour: Day Trip from Rome with Lunch & Wine

    A comfortable, air-conditioned coach will pick you up in Rome. As you leave the city behind for rolling hills, your expert, English-speaking tour guide will fill you in on Tuscany’s rich culture and answer any questions you might have about the day ahead.  First is a walking tour in the hill town of Montepulciano, led by a local expert guide, taking in an ancient but still-functioning wine cellar and ruins that pre-date Rome. Next is San Biagio, a picturesque church resting below the town at the point where the Val d’Orcia fades into the Val di Chiana. In the midst of a breathtaking landscape overlooking the Tuscan hills, the classic-style church, with its travertine facade welcoming in the sunlight, is a 16th-century Renaissance masterpiece with exquisite decorations inside. Just a short drive away is the highlight of any trip to Tuscany: lunch. In the wine cellar of an authentic vine...

    Easy to meeting point, great guide (Jon), lunch was excellent, wine excellent ( my only gripe was small amounts) but great quality.

  • From Siena: San Gimignano, Montalcino & Wine Tasting

    2. From Siena: San Gimignano, Montalcino & Wine Tasting

    The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers, a UNESCO World Natural and Cultural Heritage Site. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops. San Gimignano is also the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. The tour continues on to Monteriggioni, the ancient crown-shaped fortress that appeared on Italy’s old 100-Lire currency. The 13th-century walls feature 14 towers that Dante likened to the giants in his Inferno. Afterwards, you’ll stop at a winery for a lunch of salami, cheese, and other local products, accompanied by a tasting of Chianti wines. Visit Val d’Orcia, another Tuscan jewel and ...

    My wife and I enjoyed the experience. If you want a hardcore wine tour, this is not for you. But if you want a tour of Of beautiful Tuscany, see San Gimignano and Montalcino, and check out a couple wineries, this is perfect. We enjoyed both wineries very much and we appreciated that the driver of our tour bus would stop at picturesque locations so we could get great pics of San Gimignano from a distance and the Chianti valley. It was more of a 10 hour tour than 11 but fun nonetheless.

  • Pienza and Montepulciano Wine Tour from Siena

    3. Pienza and Montepulciano Wine Tour from Siena

    Enjoy a day of culture, wine, and food as you visit some of the most impressive towns and villages in Tuscany. Go to 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 tra...

    Excellent wine tasting in Montalcino!!!! Lucia’s knowledge of wine and history was enlightening!!! Best tasting ever.

  • From Florence or Siena: Montepulciano Wine Tour with Lunch

    4. From Florence or Siena: Montepulciano Wine Tour with Lunch

    Start with pickup from your hotel in the morning and travel first to Brunello, a boutique family-run winery and one of the most famous in the area. Enjoy tastings of some high-quality wines on site. Travel to the second winery for some tastings, before you visit the town of Pienza, which is known as the "pearl of Valdorcia". In the early afternoon, explore the village of Montepulciano. Make your way to an underground winery cellar, where you will enjoy a delicious lunch of local products, paired with in-house wines, before being returned to your accommodation.

    This entire experience was amazing. Starting off, they pick you up at your hotel. They went out of their way to accommodate my group as we bought our tickets only a few hours before. We did the brunello tour. It was a 10/10 experience. The vineyards were stunning, the wine was delicious, and the organization of the whole tour was outstanding. You absolutely MUST do this tour if you can. It was one of the most memorable days of my life.

  • Pienza and Montepulciano Full-Day Wine Tour

    5. Pienza and Montepulciano Full-Day Wine Tour

    Explore the wine lands and medieval villages of Tuscany on a full-day tour from Florence. Escape the “Cradle of the Renaissance” to sample some of the most celebrated wines in all of Italy. 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.

    This tour covered the wine area that we wanted to experience and we were not disappointed. Our guide, Alberto, was excellent! Be prepared to climb some steep hills in these villages.

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

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

    Escape the hustle and bustle of Florence and experience the heart of Tuscany by visiting the enchanting Val D’Orcia, a UNESCO World Heritage Site. Explore the beautiful towns of Montalcino, Pienza and Montepulciano and enjoy two different wine tastings and savour the famous Pecorino cheese! The tour starts with a wine tasting session in Montalcino, the land of the world-renowned Brunello wine. Here you will be enchanted by the outstanding charm of a special and definitely worth visiting wine cellar/museum. The estate has a rich history: it once belonged to the powerful Piccolomini family, whose members included Pope Pius II. Next you move up to the peak of the town, where a magnificent sight will take your breath away: sunny rolling hills, ancient oaks, picturesque olive groves, scenic country roads winding through perfect vineyards and isolated cypress trees atop hills. The tour con...

    It was a great tour except we only had one very small cheese tasting at the end of the tour. I expected a bit more wine and cheese for the tasting. Otherwise, it was a great tour with an amazing tour guide and driver.

  • From Siena: Pienza and Montepulciano Small-Group Tour

    7. 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 cent...

    Highlight of our trip Georgia was knowledgeable and entertains and a perfect host and teacher.

  • From Rome: Private Day-Tour of Tuscany

    8. 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 Montalcino. If you have a taste for Tuscany but just a short time in Italy, this tour is for you! A comfortable air-conditioned car or minivan will collect you in Rome and by mid-morning, you will be in the ancient Etruscan town of Montepulciano. The next stop is at the vineyards of Montalcino. This is where one of Italy’s best wines, Brunello di Montalcino, is produced. Absorb views over some of Tuscany’s most beautiful vineyards before heading to Sant’Antimo Abbey where, with a bit of luck, you’ll be just in time to hear the monks perform Gregorian chants. Your private driver will take you out of town to a beautiful Tuscan vineyard. At lunch, enjoy a wine tasting accompanied by bruschetta and three ...

  • From Rome: Full-Day Trip to Tuscany

    9. From Rome: Full-Day Trip to Tuscany

    During this tour around Tuscany you'll see the medieval architecture of towns such as Montepulciano, Pienza, Monteriggioni and Siena. You’ll see the winemaking process, have a chance to taste some of the region’s fine wines and enjoy a lunch of tasty regional specialties. The town of Montepulciano was a crucial trading center for Tuscany from the Middle Ages through the Renaissance. Its fame today derives from its world-renowned red wine. Proceed to the town of Montalcino, which has always been of major importance to the region due to its strategic hilltop position. It is home to Brunello, the well-known Tuscan red wine. Brunello is produced exclusively from the Sangiovese Grosso grape. The country’s average annual production is nearly 8 million bottles. Next on your tour is a stop in Siena, where you’ll see the medieval towers and alleyways that characterize this elegant town. The Pi...

  • From Florence: Val D’Orcia Full-Day Wine Tasting Tour

    10. From Florence: Val D’Orcia Full-Day Wine Tasting Tour

    Meet your guide in Florence and drive in total comfort amongst beautiful countryside, to reach the heart of the southern province of Siena and its marvelous wine regions Orcia and Montepulciano. Start by visiting the first winery of the day where you will enjoy a private tour of the cellars, receive a full explanation of the wines and get to taste three different DOC Val D’Orcia wines. Enjoy lunch at an organic agricultural farm located in the Pienza countryside and admire the panoramic views of the Val d'Orcia valley from the terrace. Here, sample some sheep and goat cheeses made from raw milk and paired with home-made wood-oven baked bread, jam and honey. Learn about the entire process of cheese production from hand milking to the final product. Continue your tour in the afternoon with a visit to the famous town of Montepulciano. Head to your final stop, a family-run winery and enjoy...

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What people are saying about Pienza

Overall rating

4.6 / 5

based on 179 reviews

It was a day full of wonderful experiences! Our guide Andrea was so knowledgeable and helped us immerse in history of Tuscany and Rome! We had some great tour with a local guide in Montepulciano, tasty lunch and wine tasting in a local winery and great free time in Pienza. Highly recommend!

I can really recommend this day trip. Our guide Andrea gave us excellent information in an interesting way about history of Technology Italy and the in Tuscanny. The landscape is marvellous, so was the food and wine. Good mixture of walking and relaxing.

Easy to meeting point, great guide (Jon), lunch was excellent, wine excellent ( my only gripe was small amounts) but great quality.

Excellent wine tasting in Montalcino!!!! Lucia’s knowledge of wine and history was enlightening!!! Best tasting ever.

Emiliano was very pleasant and interacted with everyone.