Top 5 Charming Cities in Tuscany to Include in Your Rome Itinerary

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Bungiorno and welcome to Stefano’s RomeCabs, Rome’s top-rated company for private Tuscany tours from Rome. Tuscany, with its picturesque landscapes and rich cultural heritage, is a destination that enchants travelers worldwide. There are many beautiful Tuscan towns that deserve a day dedicated to a day trip to Tuscany during your stay in Rome. In this blog post, we will explore the top five charming cities in Tuscany: Pienza, Cortona, Montepulciano, Montalcino, and Arezzo.

These cities offer a perfect blend of history, architecture, culinary delights, and breathtaking views. On Stefano's RomeCabs private tours in Italy, you can easily incorporate these destinations into your itinerary and experience the true essence of Tuscany.


Top 5 Charming Cities in Tuscany to Include in Your Rome Itinerary




1.  Pienza: The Jewel of Val d'Orcia


Located in the heart of Val d'Orcia, Pienza is a small Renaissance town that exudes charm and elegance. Designed by Pope Pius II as a "Utopian City," Pienza showcases exceptional architecture, quaint streets, and stunning views of the surrounding countryside.


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Pienza’s origins can be traced back to the 15th century when Pope Pius II, who was born  Enea Silvio Bartolomeo Piccolomini in the village of Corsignano, decided to transform his birthplace into a model Renaissance city. Then, the village of Corsignano was renamed Pienza in honor of the homegrown Pope Pius II.

Under the guidance of renowned architect Bernardo Rossellino, Pienza was redesigned with grandeur and precision. The vision was to create an ideal city that showcased the principles of Renaissance urban planning and architecture. The result was a masterpiece of harmonious design, with wide streets, elegant buildings, and spacious piazzas that epitomized the ideals of the time.

Pope Pius II, known as a humanist and lover of the arts, sought to create a place that reflected his values. He encouraged the construction of beautiful buildings, including the Palazzo Piccolomini, which served as his residence, and the stunning Pienza Cathedral, a testament to the town's spiritual significance.


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The transformation of Pienza into a Renaissance gem was not only an architectural endeavor but also a cultural one. Pope Pius II envisioned Pienza as a center of humanistic learning and a haven for artists and intellectuals. The town became a hub of creativity and scholarship, attracting renowned thinkers and artists of the time.

Piazza Pio is a picturesque piazza flanked by architectural gems such as the Cathedral of Santa Maria Assunta, the Palazzo Piccolomini, and the Palazzo Comunale. Immerse yourself in the Renaissance atmosphere as you soak in the beauty of these remarkable structures.

You will be surprised to know how many UNESCO World Heritage sites in Tuscany you can see on our tours. Today, Pienza stands as a living testament to its Renaissance heritage. The town's historic center, a UNESCO World Heritage site, enchants visitors with its perfectly proportioned buildings, harmonious layout, and breathtaking views of the resplendent surrounding Val d'Orcia, also a UNESCO World Heritage Site. It is a place where the spirit of Pope Pius II and the Renaissance period lives on, inviting visitors to step back in time and experience the grandeur of a bygone era.


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Savor Pienza’s pecorino cheese: Pienza is renowned for its delectable pecorino cheese, made from sheep's milk, Pecorino di Pienza. Take the opportunity to visit a local cheese shop and savor the distinct flavors of this Tuscan delicacy. Pair it with a glass of regional wine for a true gastronomic delight. We also dedicated an informative article on what to see and do in Pienza.

Be awed by Pienza's panoramic views: Wander through the narrow streets of Pienza and make your way to the town's edge along charming lanes with romantic names such as "Via dell'Amore" (Love Lane), "Via del Bacio" (Kiss Lane), where you'll be rewarded with breathtaking panoramic views of the Val d'Orcia valley. The sight of the rolling hills, vineyards, and olive groves stretching into the distance is a true feast for the eyes and the soul.

As you stroll through Pienza's charming streets, admiring the architecture and soaking in the tranquil atmosphere, you can't help but feel the weight of history and the lasting impact of Pope Pius II's vision. Pienza is a testament to the power of human creativity, a place where the past and present coexist in perfect harmony.

You may visit Pienza on our Valley of Paradise Tuscany Tour from Rome, and Enchanting Tuscany Day Tour from Rome.


2.  Montepulciano: Wine and Renaissance Beauty


Famous for its exquisite wine, Montepulciano is a hill town overlooking Val di Chiana valley that combines the pleasures of the palate with architectural wonders that effortlessly blends wine, history, and Renaissance beauty.


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As you wander through its medieval streets, you'll be enchanted by the architectural splendor of the Renaissance palaces, churches, and piazzas that grace the town. Thousands of our guests booked our Tuscany Tour from Rome to Montepulciano and Pienza for a fun-filled day trip from Rome to Tuscany.

Montepulciano’s origins can be traced back to the Etruscan civilization (an advanced Pre-Roman civilization that dominated central Italy), making it one of the oldest settlements in the region. Throughout the centuries, Montepulciano thrived under different powers, including the Romans and the medieval city-states. The town's strategic location along the trading route between Florence and Rome contributed to its prosperity, as it became a hub for commerce and cultural exchange.

During the Renaissance, Montepulciano experienced a golden age of artistic and intellectual achievement. The ruling Medici family recognized the town's potential and bestowed patronage upon local artists and architects, resulting in the construction of magnificent palaces, churches, and public squares.


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The grand Piazza Grande, flanked by Renaissance palaces, is the centerpiece of the town and a testament to its cultural significance. The iconic Duomo, with its exquisite facade and impressive interior, showcases the town's devotion to art and spirituality.

But it's the exquisite wine that truly sets Montepulciano apart. The vineyards that surround Montepulciano have become synonymous with the region's viticultural heritage, and wine enthusiasts flock to the town to sample its celebrated vintages.

The town is renowned for its Vino Nobile di Montepulciano, a robust and elegant red wine that has been produced since the 14th century from the local Sangiovese grapes, tantalizing the taste buds with its rich flavors and velvety texture. Crowned “King of All Wine”, Montepulciano still reigns supreme for its prestigious local wines that are available for wine tasting at wineries in Montepulciano since many local wineries operate their own wine shops with historical wine cellars that you can visit. Take a moment to savor a glass of this exceptional wine while basking in the stunning panoramic views of the surrounding Tuscan countryside. 


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Montepulciano stands as a living testament to its storied history. Whether you're strolling through its historic center, sipping a glass of Vino Nobile, or simply taking in the panoramic views from the town's vantage points, Montepulciano offers an immersive experience into Tuscany's rich history.

Wine lovers can toast their Tuscany adventures on our Tuscany wine tours from Rome to Montepulciano, and experience the magic and flavors of Tuscany on our Tuscany Castles and Wine Tour from Rome.


3.  Cortona: History and Panoramic Views

Perched on a hilltop also overlooking the Val di Chiana, Cortona is a charming town brimming with history and stunning vistas. Lose yourself in its labyrinthine streets, visit the impressive Etruscan Museum, and soak in the captivating views of the surrounding countryside. Cortona's laid-back atmosphere will make you feel like a local. Only about 2.5 hours from Rome, its location is perfect for a day trip from Rome to Cortona.



Cortona’s roots reach as far back as the Etruscan civilization, making it one of the oldest continuously inhabited cities in Italy. Its origins can be traced back to the 9th century BC when the Etruscans established a settlement in this strategic location. The Etruscans thrived in Cortona, leaving behind impressive archaeological remains that tell the story of their advanced civilization. As you explore the city, you can discover remnants of Etruscan walls, tombs, and artifacts that offer a glimpse into Cortona's ancient past.

Over the centuries, Cortona experienced the influence of various civilizations and powers. It became a Roman colony in the 3rd century BC, and Roman ruins can still be found in the city, including the impressive remains of a Roman theater.

During the Middle Ages, Cortona grew into a prominent city-state, known for its strategic position and fortified walls. It became a hub for trade and commerce, attracting merchants and artisans from all over Italy. The city's wealth and prosperity during this period can be seen in its beautiful palaces, churches, and public squares.


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One of the most significant chapters in Cortona's history is its connection to the famous painter and writer, Fra Angelico. Born in the city in the 15th century, Fra Angelico left a lasting artistic legacy with his stunning frescoes in the Monastery of San Marco in Florence.

Today, Cortona stands as a living testament to its rich history. Its charming medieval streets, adorned with stone buildings and quaint shops, offer a glimpse into its storied past. Visitors can explore historical sites, such as the impressive Duomo and the Palazzo Comunale, and wander through the city's narrow alleys that seem frozen in time.

Cortona's fascinating history is a tapestry woven with the threads of ancient civilizations, medieval grandeur, and artistic brilliance. It is a place where the past and present coexist harmoniously, inviting visitors to immerse themselves in the captivating stories and traditions that have shaped this remarkable city.

4. Arezzo: Artistic Heritage and Elegance


With its rich artistic heritage and elegant ambiance, Arezzo is a city that captivates visitors. Explore the medieval old town, visit the Basilica of San Francesco with its remarkable frescoes, and stroll through the beautiful Piazza Grande, the heart of the city's social and cultural life and where the famous Giostra del Saracino takes place in the summer. Arezzo offers a delightful blend of history, culture, and Tuscan charm.


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Arezzo also vaunts a rich and fascinating history that spans over 2,000 years. Legend has it that the city was founded by the Etruscans in the 9th century BC, but it truly flourished during the Roman era. As an important Roman trading hub, Arezzo enjoyed prosperity and grew into a thriving city.

Throughout the centuries, Arezzo witnessed the rise and fall of different powers. It became a flourishing medieval city-state in the Middle Ages, known for its skilled artisans and vibrant trade. The city was a prominent center for banking, textile production, and goldsmithing, which contributed to its wealth and cultural influence. 

Arezzo's historical significance is evident in its architecture and landmarks. The city's old town boasts an array of medieval and Renaissance structures, including the impressive Cathedral of San Donato, which dates back to the 13th century. The Basilica of San Francesco is renowned for its frescoes by the illustrious painter Piero della Francesca, showcasing the artistic brilliance of the time.


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Over the years, Arezzo has also witnessed significant events. In 1289, it was the site of the famous Battle of Campaldino, where the Florentine and Arezzo forces clashed. This battle played a crucial role in the political dynamics of Tuscany.

Arezzo was also where the award-winning movie Life is Beautiful was filmed.

Beyond its artistic allure, Arezzo boasts a warm and welcoming ambiance, inviting you to savor the authentic flavors of Tuscan cuisine and immerse yourself in the rhythms of daily life.  There are so many wonderful things to see and do in Arezzo.  From the monthly Antiques Fair and Medieval Festivals to the hidden corners of its enchanting old town, Arezzo is a city that beckons you to discover its secrets and create lasting memories.

Dedicate a day for a day trip from Rome to Arezzo and Cortona and experience the charm and beauty of these exceptional Tuscan cities.


5.  Montalcino: A Wine Lover's Paradise


Renowned for its exquisite Brunello di Montalcino wine, Montalcino will enchant wine enthusiasts. Beyond the wine, Montalcino's allure lies in its serene atmosphere and breathtaking vistas, offering a tranquil retreat from the bustling world. As you explore the narrow streets of Montalcino, you can't help but feel the weight of its history. 

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Fortress of Montalcino, wander through the ancient walls of the Fortress of Montalcino, stroll along its atmospheric streets, and indulge in wine tastings at the local wine shops throughout the town.

Like most of Tuscany’s historical hill towns, Montalcino has a storied history that spans centuries. This enchanting town traces its roots back to the Etruscan era when it served as a strategic outpost overlooking the surrounding landscape.

However, it was during the medieval period that Montalcino truly flourished. The town grew in importance as a fortified stronghold, boasting impressive city walls and a formidable fortress. These defensive structures stood as a testament to the tumultuous times when rival city-states vied for control of the region.

In the 14th century, Montalcino became an independent city-state, governed by the influential Sienese Republic. The town's strategic position and thriving economy allowed it to prosper, attracting merchants, artists, and scholars from far and wide. Its streets buzzed with activity, and its palaces and churches were adorned with exquisite art and architecture.

The Renaissance brought further prosperity and cultural splendor to Montalcino. The town became a hub for learning and artistic expression, drawing renowned painters, sculptors, and poets. The grand Palazzo dei Priori, a symbol of the town's civic pride, was constructed during this period and stands as a testament to Montalcino's historical significance.


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The highlight of Montalcino is its coveted Brunello di Montalcino wine, a rich and velvety red that embodies the essence of Tuscany. Take a sip of this exquisite wine as you overlook the vineyard-covered hills, where rows of grapevines bask in the warm Tuscan sun. Along with Montepulciano,  Montalcino is a favorite destination for Wine Tasting Tours from Rome.

Montalcino's captivating history, combined with its breathtaking vistas of vineyards and rolling hills, make it a must-visit destination for those seeking to experience the essence of Tuscany. Whether you're wandering through its historic center, sipping a glass of Brunello di Montalcino, or simply basking in the timeless beauty of the landscape, Montalcino is a place that leaves an indelible mark on the heart and soul.

Wine enthusiasts revel in a day of wine tasting and Tuscan beauty on our  Tuscany Wine Tour from Rome.


Exploring Tuscany’s charming cities of Pienza, Cortona, Montepulciano, Montalcino, and Arezzo will add a touch of authenticity and charm to your Rome itinerary. These cities showcase the rich heritage, breathtaking landscapes, and exceptional culinary traditions that Tuscany is famous for.

On Stefano's RomeCabs Tuscany Tours from Rome, you can seamlessly include these captivating cities in your itinerary and embark on an unforgettable journey through the heart of Tuscany. So, indulge in the beauty, history, and flavors of these top five charming cities and experience the magic of Tuscany.  We look forward to seeing you soon in Italy!

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