In the south of Tuscany, nestled among rolling hills and ancient forests, lies the city of Arezzo, a small medieval gem set in a territory rich with natural and architectural attractions. In this article, we’ll offer some suggestions on what to see in Arezzo and its province, adding a few strategic stops to your itinerary.
Hotel booked, suitcases packed, car loaded! So, you're off to Arezzo: where to start? Naturally, from the historic center of the capital: begin at the Medici Fortress for a panoramic view of the city, or from the characteristic Piazza Grande. Sloping towards the center like the more famous Piazza del Campo in Siena, it hosts the traditional equestrian tournament, the Joust of the Saracen, twice a year in June and September. If you're looking for an authentic experience, you might plan your trip during one of these times and be transported back in time by the sumptuous and colorful costumes of the noble knights who compete in the tournament.
Every first Sunday of the month and the preceding Saturday, the historic center hosts the Arezzo Antique Fair, known as the Portobello of Italy—a unique opportunity to find unique treasures and experience the originality of local craftsmanship firsthand. During the fair, the Museum of the Porta Sant’Andrea District is also open, showcasing precious memorabilia from the Arezzo jousts of the last 100 years. If you prefer sacred art, the Basilica of San Domenico houses a splendid crucifix by Cimabue, while the Basilica of San Francesco is home to one of the grandest frescoes of the Italian Renaissance, Piero della Francesca’s Legend of the True Cross.
Leaving the city walls behind and embarking on a road trip through the province of Arezzo, you can immerse yourself in the hidden treasures of the villages that dot the Aretine countryside. Cortona, for example, perched on the slopes of the hills overlooking the Val di Chiana, offers breathtaking views and a unique atmosphere. Surrounded by vineyards and olive groves, it is an ancient village with numerous and peculiar religious architectures, including the Basilica of Santa Margherita with its richly colored vaults. From here, you can move towards Anghiari, with its sixteenth-century walls and the suggestive panorama overlooking the Tiber Valley.
The province of Arezzo boasts many other villages of great charm and historical interest that you might want to include in your travel program: for instance, Montepulciano and Montalcino combine the charm of medieval cobblestone streets and breathtaking views with renowned wine production, famous throughout Italy and the world. If you enjoy good wine, it's definitely worth stopping at one or both of these villages!
Montalcino, like other villages in the province, is located in Val D’Orcia, an expansive hilly area stretching from the south of Siena to Monte Amiata. In April and May, it bursts into a sea of yellow, red, purple, and green hues from seasonal blooms: a unique panorama to traverse by car and capture in spectacular photographs.
If you love venturing into unspoiled nature, there’s a stop you absolutely cannot miss during your road trip through Arezzo: the Casentinesi Forests. This protected natural heritage encompasses majestic mountains, ancient forests, and crystal-clear streams. Here, among the ancient tree branches, you might encounter wild animals and breathe the fresh air that only unspoiled nature can offer—roll down the window and enjoy the journey!

To reach these extraordinary places, you can rent a car in Arezzo or, if you wish to start from a different city, turn to other Locauto rental points in Tuscany: