Itinerary

Montepulciano
Montepulciano, a jewel of Tuscany, is a medieval hilltop town renowned for its Renaissance architecture, stunning landscapes, and world-famous wine. Surrounded by rolling vineyards, this charming town is home to the prestigious Vino Nobile di Montepulciano, one of Italy’s finest wines. As you stroll through its winding cobblestone streets, you’ll discover elegant palaces, ancient churches, and breathtaking panoramic views of the Tuscan countryside. The heart of Montepulciano is Piazza Grande, a picturesque square lined with historic buildings, including the majestic Palazzo Comunale and the stunning Duomo. Wine lovers can visit traditional cellars carved into the town’s underground vaults for tastings of the region’s celebrated wines. With its blend of history, culture, and exquisite flavors, Montepulciano offers an unforgettable experience, capturing the essence of Tuscany’s timeless charm.
4 hours
Montalcino
Montalcino, a picturesque hilltop town in Tuscany, is world-famous for producing Brunello di Montalcino, one of Italy’s most prestigious wines. Surrounded by rolling vineyards and olive groves, this medieval gem offers breathtaking panoramic views of the Tuscan countryside. Its historic center is a delightful maze of narrow streets, charming piazzas, and elegant stone buildings. The imposing 14th-century fortress, Rocca di Montalcino, stands as a symbol of the town’s rich past, offering stunning views from its ramparts. Visitors can explore historic churches, such as Sant’Agostino and the Abbey of Sant’Antimo, a beautiful Romanesque monastery just outside town. Wine enthusiasts can enjoy tastings at traditional wineries, discovering the deep flavors and heritage of Brunello. With its perfect blend of history, culture, and gastronomy, Montalcino is an unmissable destination for those seeking the authentic beauty of Tuscany.
4 hours
Cortona
Cortona, a charming hilltop town in Tuscany, is a place where history, art, and breathtaking landscapes come together. Enclosed by ancient Etruscan walls, this medieval gem offers stunning panoramic views of the Val di Chiana and Lake Trasimeno. Its historic center is a maze of narrow stone streets, lively piazzas, and elegant Renaissance buildings. The heart of Cortona is Piazza della Repubblica, home to the grand Palazzo Comunale. Art lovers can explore the MAEC Museum, which houses fascinating Etruscan artifacts, and the Church of San Francesco, a masterpiece of medieval architecture. Cortona is also famous for its role in the book and film *Under the Tuscan Sun*, adding to its romantic allure. Whether you’re savoring local Tuscan cuisine, admiring breathtaking sunsets, or soaking in the town’s rich history, Cortona offers an unforgettable experience filled with charm, culture, and timeless beauty.
3 hours