In Tuscany, this journey becomes an authentic experience. Scenic roads, medieval villages, historic wineries, and hills shaped by time create the perfect itinerary for those who want to explore the region in an immersive way.
Among the most fascinating destinations, Montepulciano and the Val d'Orcia area are must-see stops for anyone wanting to explore Tuscany at a relaxed pace and with complete freedom.
Having a car gives you the freedom to travel without time constraints, reach places off the beaten path, and customize your itinerary based on your own interests.
For those arriving by train, the ideal starting point is the Chiusi station, a strategic hub between Umbria and Tuscany. Here you can pick up your rental car with Revirent24, a company specializing in car and van rentals, offering modern vehicles and flexible services even without a credit card.
Recommended Itinerary: 3 Days Discovering the Most Authentic Tuscany
Thanks to its central location, Montepulciano is the perfect starting point for exploring some of the most charming villages of southern Tuscany by car.
We suggest a 3-day itinerary, easy to follow and designed for those who love to combine beautiful landscapes, local culture, and food and wine excellence.
Montepulciano: History, Wine, and Views
Montepulciano is a gem in the heart of Tuscany, known as the "pearl of the Renaissance" for its extraordinary blend of history, art, and landscapes. This charming village sits atop a hill surrounded by stretches of vineyards and olive groves, a place where time seems to stand still.
The historic center is the heart of the town, where you'll find Piazza Grande, home to some of the most important buildings, such as the Cathedral, an architectural masterpiece dominating the square, and the Town Hall, symbol of the city’s administrative and cultural life since the Middle Ages.
Montepulciano is also internationally renowned for the production of the famous Vino Nobile, a wine of excellence that has made this village known worldwide. A must-see are its underground cellars, ancient storerooms carved into tuff rock where you can discover the secrets of winemaking and taste Vino Nobile di Montepulciano. Among the most famous are the Ercolani and De’ Ricci cellars, which offer a full sensory experience, blending history, flavors, and aromas that tell the passion and tradition of this land.
Outside the historic center stands another architectural and scenic treasure: the Temple of San Biagio, a Renaissance church surrounded by the green countryside.
Pienza and Monticchiello: Two Villages, One View
Along the spectacular SP146, one of the most beautiful scenic roads in Tuscany, nature blends harmoniously with history and culture. This road leads directly to Pienza, a Renaissance gem born from the dream of Pope Pius II, who wanted to transform his hometown into a perfect example of an ideal city. Today, Pienza is recognized as a UNESCO World Heritage Site.
Walking through the streets of Pienza, you can admire noble palaces, including the Palazzo Piccolomini, built for the Pope's family and symbolizing the elegance and power of the era.
In addition to art and architecture, Pienza also offers a sensory journey through its typical products, especially the famous pecorino cheese, which can be tasted in the many artisan shops of the village, where tradition and quality come together to delight the palate.
The village's scenic viewpoints are another reason to visit. From these spots, you can admire the stunning Val d'Orcia.
A few kilometers from Pienza lies Monticchiello, a small and lesser-known but captivating village. Monticchiello is also famous for its "Poor Theater", a theatrical tradition involving the entire community and representing a unique form of popular culture. The local crafts, handed down through generations, further enrich the visit by offering unique, handmade items.
Visiting Pienza and Monticchiello offers a precious opportunity to discover two different but complementary realities, united by an extraordinary landscape and a rich, captivating history.
Radicofani and Città della Pieve: Between Fortresses and Art
The third day of your itinerary takes you south to discover two lesser-known but equally fascinating and historic villages: Radicofani and Città della Pieve.
These places, although less visited than Tuscany and Umbria’s most famous destinations, offer authentic and surprising experiences that showcase traditions, art, and breathtaking views.
Radicofani is a village perched on a hilltop overlooking the Val d'Orcia, famous for its imposing Fortress of Ghino di Tacco. This medieval stronghold, a testament to a past of strategy and adventure, offers a spectacular 360-degree view of the surrounding hills, allowing you to admire one of Tuscany’s most stunning landscapes.
Città della Pieve, located on the border between Umbria and Tuscany, can be reached in less than an hour by car. This village stands out for its refined elegance and the characteristic red color of its alleys, paved with typical local terracotta.
Città della Pieve is also famous as the birthplace of Renaissance painter Pietro Perugino, whose works enrich the churches and palaces of the town center. Among the must-sees is the fresco of the Adoration of the Magi, an extraordinary example of sacred art.
This is a place where traditional crafts still thrive, thanks to numerous ceramics workshops and shops offering high-quality local products. Here, you can find and purchase unique items crafted with skill and passion, telling the story and culture of this land.
The views over Lake Trasimeno complete the experience, offering natural scenery of great beauty that perfectly complements the urban environment.
With this itinerary, you’ll enjoy a full experience of historic villages, great food, excellent wines, and charming roads — all with the freedom only a rental car can provide.
Summer in Montepulciano: Events and Traditions to Enjoy
Summer in Montepulciano is a unique opportunity to immerse yourself in the culture, traditions, and liveliness of this beautiful Tuscan village.
Between July and August, the town comes alive with a series of historical and cultural events that attract visitors from all over Italy and abroad, offering engaging experiences.
One of the most significant events is the Bravio delle Botti, held on the first Sunday of August. This traditional competition among Montepulciano’s eight districts features a spectacular uphill race where participants roll large wine barrels through the steep streets of the historic center. The event is accompanied by a grand historical parade in medieval costumes, traditional games, live music, and festive moments celebrating the town's history and identity. The Bravio delle Botti is a true collective ritual involving the entire community.
The summer calendar also features many other notable events.
On August 10th, for the night of San Lorenzo, the magical event Calici di Stelle takes place. This evening is dedicated to tasting the region’s famous wines, such as Vino Nobile di Montepulciano and Rosso di Montepulciano, in a magical atmosphere under the stars. The streets of the historic center come alive with food and wine stands, live music, and performances, creating a multisensory experience.
During Ferragosto, Montepulciano hosts the Bruscello Poliziano, a popular theatrical performance in Piazza Grande. This ancient form of folk theater features local actors performing stories and legends related to the area, offering a vivid portrayal of the community’s culture and roots.
For music lovers and wine enthusiasts, the evening Sunset Vineyard events are a must. Held in local wineries, these events combine tastings of selected wines with 80s and 90s music concerts. These evenings are designed for moments of relaxation and fun in a picturesque setting.
Not far from Montepulciano, in Montalcino, the Jazz & Wine festival takes place from July 9th to 14th. This event blends jazz music with the area’s wine excellence. It’s an opportunity to explore the region’s flavors and atmosphere in a high-level musical context, further enriching the summer schedule in Tuscany.
Attending these events is a way to experience a place of connection and sharing, where tradition and modernity harmoniously intertwine.
Why Choose Revirent24 for Your Road Trip?
Planning a road trip through Montepulciano and the Val d'Orcia is easy, especially with the right partner by your side.
Thanks to its strategic location, Revirent24 is the ideal and convenient solution for those who want to rent a car quickly and hassle-free.
This service lets you immediately begin your itinerary to some of the most beautiful destinations in Tuscany, such as Montepulciano, Pienza, Radicofani, and the other stunning villages of the Val d'Orcia.
Choosing Revirent24 means exploring these areas full of history, culture, and unique landscapes with freedom and flexibility, fully enjoying each stop without depending on public transport or fixed schedules.
With Revirent24 you can:
- Rent a car even without a credit card
- Choose from cars, vans, or 9-seater minibuses — ideal for small groups or families
- Pay in cash, credit card, debit card, or bank transfer
- Add useful options such as child seats or additional drivers
Additionally, they offer:
- Short-term rentals for a weekend or a few days
- Medium and long-term rentals, perfect for longer stays
All vehicles come with unlimited mileage, 24/7 assistance, and the option to return the car to a different location, even in a different city, providing maximum flexibility in your travels.
Exploring Montepulciano and its surroundings by car is an experience that combines freedom, comfort, and the chance to enjoy each place at your own pace.
With a carefully planned itinerary and the support of a reliable partner like Revirent24, your trip to Tuscany will be simple, safe, and unforgettable.
Booking a rental car with Revirent24 means choosing a flexible service, with modern vehicles, stress-free payment options, and 24/7 dedicated assistance.
Revirent24 is ideal for anyone seeking a clear and transparent rental experience, with a service tailored to those who want to discover the region’s wonders in total freedom and safety.
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