Country Roads of Umbria & Tuscany - Classic Group

Tuscany, Italy, is a region where the essence of Italy's beauty, history, and culture is captured in its rolling hills, timeless villages, and world-class art. Famous for its postcard-perfect landscapes, Tuscany is where cypress-lined roads lead to centuries-old hilltop towns like Montepulciano and Montalcino, which are steeped in history and offer some of Italy's finest wines, including the renowned Brunello di Montalcino. Tuscany is a treasure trove for lovers of art and architecture, boasting some of the most important works from the Renaissance period. The city of Florence, Tuscany’s capital, is a UNESCO World Heritage Site and home to the Uffizi Gallery, where you can witness masterpieces by Michelangelo, Botticelli, and Leonardo da Vinci. A visit to the Cathedral of Santa Maria del Fiore with its iconic terracotta dome is essential, offering breathtaking views of the city and its surrounding countryside.

For those drawn to medieval charm, the walled city of Siena is a must-see. Famous for the Palio, a thrilling horse race held twice a year in its central Piazza del Campo, Siena's medieval streets unfold into a captivating blend of Gothic architecture and Tuscan culture. Visit the Siena Cathedral, a black-and-white striped marvel of Romanesque-Gothic architecture, which houses works by Donatello and Michelangelo. Siena also offers an authentic Tuscan culinary experience with local dishes such as pici pasta and ribollita soup, paired with robust local wines like Chianti Classico.

No trip to Tuscany would be complete without exploring its breathtaking countryside, especially the Val d'Orcia, another UNESCO World Heritage site. Known for its undulating hills, vineyards, and olive groves, the Val d'Orcia offers picture-perfect scenery that has inspired painters for centuries. Towns like Pienza, designed by Pope Pius II as the “ideal Renaissance city,” offer intimate experiences of Tuscan life. Wander through charming cobblestone streets, sample pecorino cheese, and gaze at the landscapes that stretch as far as the eye can see.

Fun fact: Tuscany is not just about history and art; it's also the birthplace of one of Italy's most iconic cultural treasures—the gelato. The first gelato is believed to have been created in the 16th century by Bernardo Buontalenti, a native of Florence, who impressed the Medici court with his delicious, creamy invention. Today, Tuscany continues to be a fantastic place to savor artisanal gelato, making it a perfect stop for food lovers looking to indulge in authentic Italian flavors.

San Gimignano, a stunning medieval hilltop town in Tuscany, Italy, is often called the "Medieval Manhattan" due to its remarkable skyline of ancient towers. Encircled by 13th-century walls, the town is a UNESCO World Heritage site that offers a mesmerizing journey back in time. As you stroll along the cobbled streets of the historic center, you'll be enchanted by the preserved Romanesque and Gothic architecture, from charming piazzas to grand churches. The Collegiata di San Gimignano, a Romanesque cathedral, is a must-visit, renowned for its vivid frescoes that depict scenes from the Old and New Testaments, crafted by some of Italy's most celebrated artists of the 14th century.

San Gimignano's iconic skyline, once dotted with over 70 towers, was built by noble families competing for power and prestige during the Middle Ages. Today, only 14 towers remain, yet they still evoke the town's rich history and rivalries. Climb the Torre Grossa, the tallest tower in town, for panoramic views of the surrounding Tuscan countryside, with its rolling vineyards and olive groves stretching to the horizon. The climb is well worth the effort, offering a bird's-eye view of the medieval rooftops and the distant hills.

The town is not just about history; it also offers a delightful culinary experience. San Gimignano is known for its locally produced white wine, Vernaccia di San Gimignano, which has been celebrated since the Renaissance and was even praised by the likes of Dante and Michelangelo. Enjoy a glass of this crisp, golden wine at a local enoteca, paired with regional specialties such as saffron-infused dishes and wild boar ragu. For dessert, treat yourself to the world-famous gelato from Gelateria Dondoli, winner of multiple Gelato World Championships, located right in the heart of Piazza della Cisterna.

Fun fact: San Gimignano was an important stop along the Via Francigena, a major pilgrimage route that stretched from Canterbury to Rome in the Middle Ages. Pilgrims would rest and refresh in the town before continuing their arduous journey southward. Today, visitors can still walk part of this historic route, which winds through some of Tuscany's most breathtaking landscapes.

San Gimignano, a stunning medieval hilltop town in Tuscany, Italy, is often called the "Medieval Manhattan" due to its remarkable skyline of ancient towers. Encircled by 13th-century walls, the town is a UNESCO World Heritage site that offers a mesmerizing journey back in time. As you stroll along the cobbled streets of the historic center, you'll be enchanted by the preserved Romanesque and Gothic architecture, from charming piazzas to grand churches. The Collegiata di San Gimignano, a Romanesque cathedral, is a must-visit, renowned for its vivid frescoes that depict scenes from the Old and New Testaments, crafted by some of Italy's most celebrated artists of the 14th century.

San Gimignano's iconic skyline, once dotted with over 70 towers, was built by noble families competing for power and prestige during the Middle Ages. Today, only 14 towers remain, yet they still evoke the town's rich history and rivalries. Climb the Torre Grossa, the tallest tower in town, for panoramic views of the surrounding Tuscan countryside, with its rolling vineyards and olive groves stretching to the horizon. The climb is well worth the effort, offering a bird's-eye view of the medieval rooftops and the distant hills.

The town is not just about history; it also offers a delightful culinary experience. San Gimignano is known for its locally produced white wine, Vernaccia di San Gimignano, which has been celebrated since the Renaissance and was even praised by the likes of Dante and Michelangelo. Enjoy a glass of this crisp, golden wine at a local enoteca, paired with regional specialties such as saffron-infused dishes and wild boar ragu. For dessert, treat yourself to the world-famous gelato from Gelateria Dondoli, winner of multiple Gelato World Championships, located right in the heart of Piazza della Cisterna.

Fun fact: San Gimignano was an important stop along the Via Francigena, a major pilgrimage route that stretched from Canterbury to Rome in the Middle Ages. Pilgrims would rest and refresh in the town before continuing their arduous journey southward. Today, visitors can still walk part of this historic route, which winds through some of Tuscany's most breathtaking landscapes.

San Gimignano, a stunning medieval hilltop town in Tuscany, Italy, is often called the "Medieval Manhattan" due to its remarkable skyline of ancient towers. Encircled by 13th-century walls, the town is a UNESCO World Heritage site that offers a mesmerizing journey back in time. As you stroll along the cobbled streets of the historic center, you'll be enchanted by the preserved Romanesque and Gothic architecture, from charming piazzas to grand churches. The Collegiata di San Gimignano, a Romanesque cathedral, is a must-visit, renowned for its vivid frescoes that depict scenes from the Old and New Testaments, crafted by some of Italy's most celebrated artists of the 14th century.

San Gimignano's iconic skyline, once dotted with over 70 towers, was built by noble families competing for power and prestige during the Middle Ages. Today, only 14 towers remain, yet they still evoke the town's rich history and rivalries. Climb the Torre Grossa, the tallest tower in town, for panoramic views of the surrounding Tuscan countryside, with its rolling vineyards and olive groves stretching to the horizon. The climb is well worth the effort, offering a bird's-eye view of the medieval rooftops and the distant hills.

The town is not just about history; it also offers a delightful culinary experience. San Gimignano is known for its locally produced white wine, Vernaccia di San Gimignano, which has been celebrated since the Renaissance and was even praised by the likes of Dante and Michelangelo. Enjoy a glass of this crisp, golden wine at a local enoteca, paired with regional specialties such as saffron-infused dishes and wild boar ragu. For dessert, treat yourself to the world-famous gelato from Gelateria Dondoli, winner of multiple Gelato World Championships, located right in the heart of Piazza della Cisterna.

Fun fact: San Gimignano was an important stop along the Via Francigena, a major pilgrimage route that stretched from Canterbury to Rome in the Middle Ages. Pilgrims would rest and refresh in the town before continuing their arduous journey southward. Today, visitors can still walk part of this historic route, which winds through some of Tuscany's most breathtaking landscapes.