Tuscany Day Trip: Montepulciano & Pienza from Siena
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Overview
The Small-Group Montepulciano and Pienza Day Trip from Siena offers an enchanting journey into the heart of Tuscany. This guided tour takes you through the rolling clay hills south of Siena, showcasing the UNESCO-protected landscapes of the Val d’Orcia region. Experience the beauty of Pienza and Montepulciano, two of Tuscany's most charming towns.
What to Expect: This full-day bus tour immerses visitors in the beauty and culture of the Tuscan countryside. The adventure begins in Siena and travels to Crete Senesi, before venturing into the picturesque Val d'Orcia. Travelers will explore Pienza, known for its delicious pecorino cheese, and visit a local dairy farm. The tour continues to Montepulciano, where you can wander through Piazza Grande and explore the Vino Nobile cellars.
This small-group tour, limited to eight people, ensures personalized attention. Included in the tour is transportation by an air-conditioned minivan, lunch at a local farm with alcoholic beverages. The tour excludes hotel pickup and drop-off services and gratuities. Experience the very best of Tuscany with expert guides.




Highlights
Explore Pienza: Discover the 'ideal city' of the Renaissance and sample local pecorino cheese.
Visit Montepulciano: Wander through the historic Piazza Grande and explore the Vino Nobile cellars.
Enjoy a Tuscan Lunch: Savor a delicious meal with wine at a local farm in the Val d'Orcia.
Small-Group Experience: Enjoy personalized attention on this tour limited to just 8 people.
Sentiment Analysis
Customers generally had a wonderful time, praising the scenery, food, and personal attention. Some wished for a slightly less rushed pace and hotel transfers.

Customers loved the beautiful scenery and charming towns.
Many enjoyed the small group size, which made the experience more personal.
The lunch at the local farm was a highlight for many, with delicious food and wine.
Visitors appreciated the knowledgeable and friendly guide.
Some found the tour a bit rushed, wishing for more time in each location.
A few travelers mentioned that hotel pick-up and drop-off would have been more convenient.
The Journey
Siena and the Crete Senesi
Begin your adventure in Siena, a city steeped in medieval history and renowned for its stunning Piazza del Campo. Leaving Siena, venture south through the Crete Senesi, a surreal landscape of rolling clay hills sculpted by time. This lunar-like terrain offers unparalleled panoramic views and a glimpse into a unique ecosystem, making it a photographer's dream and a truly unforgettable introduction to the Tuscan countryside.
Val d'Orcia
The Val d'Orcia, a UNESCO World Heritage site, unfolds as a tapestry of gently rolling hills, cypress-lined roads, and picturesque farmhouses. This iconic landscape epitomizes the Tuscan ideal, offering postcard-perfect vistas at every turn. Its timeless beauty has inspired artists and travelers for centuries, making it an essential stop for anyone seeking the authentic heart of Tuscany.
Pienza
Step into the Renaissance in Pienza, a utopian town meticulously planned by Pope Pius II in the 15th century. Marvel at the harmonious architecture of the Piazza Pio II, the Cathedral, and the Palazzo Piccolomini. Wander through the charming streets, sample the renowned Pecorino cheese, and soak in the breathtaking views of the Val d'Orcia. Pienza offers a unique glimpse into a visionary's dream realized in stone.
Corsignano
Explore the birthplace of Pope Pius II and the Romanesque church that stands as a testament to Corsignano's enduring history. Wander through this idyllic setting, absorb the serene atmosphere, and discover hidden corners that whisper tales of a bygone era. The scenic routes surrounding Corsignano offer breathtaking views and a tranquil escape from the bustling world.
Val d'Orcia Dairy Farm
Indulge in an authentic Tuscan culinary experience at a Val d'Orcia dairy farm. Savor a wholesome lunch featuring fresh, locally sourced ingredients, including the region's famed pecorino sheep cheese. Learn about the cheese-making process, meet the farm animals, and immerse yourself in the rural lifestyle. Weather permitting, enjoy your meal on a panoramic terrace, overlooking the stunning valley below. It's a feast for the senses and a true taste of Tuscany.
Montepulciano
Ascend to Montepulciano, a majestic hilltop town boasting a rich history and stunning panoramic views stretching to the Umbrian border. Explore the grand Piazza Grande, sample the renowned Vino Nobile di Montepulciano in ancient cellars, and admire the Renaissance architecture. Discover the traces of both Siena and Florence in the town's elegant palaces and imposing churches.
Piazza Grande and Vino Nobile cellars
Delve into the heart of Montepulciano at Piazza Grande, the town's main square, surrounded by historic buildings and offering breathtaking views. Descend into the ancient wine cellars carved beneath the city to taste the prestigious Vino Nobile, a testament to the region's winemaking heritage. Explore the town's artisan shops, churches, and palaces, and imagine the excitement of the annual Bravio delle Botti barrel race.
Know Before You Go
This tour includes transport by air-conditioned minivan for a comfortable journey, as well as a delicious lunch with alcoholic beverages at a local farm. A knowledgeable driver/guide will accompany the group throughout the day. Please note that hotel pickup and drop-off are not included. Gratuities are also not included in the tour price. The meeting point is in Siena. Be sure to confirm the exact location after booking.
Hot Tip
Many travelers suggest wearing comfortable shoes, as there is a fair amount of walking involved. Also, consider bringing a water bottle to stay hydrated, especially during the warmer months.