1. Historical Tour of Castiglion Fiorentino
Duration: 2-3 hours
Description: Explore the medieval and Renaissance charm of Castiglion Fiorentino. The tour begins at the Cassero Tower, the town’s symbol, offering breathtaking views of the Val di Chio. Continue with a visit to the Collegiate Church of San Giuliano, the Archaeological Museum, and the Municipal Art Gallery, which houses works by local and Renaissance artists. Strolling through the historic center, you’ll admire the Vasari Loggia, a splendid architectural masterpiece with panoramic views of the Valdichiana.
Special Stop: The Cassero Tower, perfect for a panoramic insight into Castiglion Fiorentino’s history and landscape.

2. Archaeological and Historical Route
Duration: 2 hours
Description: Castiglion Fiorentino has deep roots in the Etruscan and Roman periods. This tour takes visitors through the Cassero Archaeological Park, home to remains of ancient Etruscan and Roman dwellings. The route also includes a visit to the Church of Sant’Angelo al Cassero, one of the town’s oldest buildings.
Special Stop: Cassero Archaeological Park, with its excavations and historical reconstructions that reveal the life of ancient Castiglione.

3. Wine and Local Flavors Tour
Duration: 3-4 hours
Description: A culinary journey combining visits to vineyards and wineries in the Valdichiana with tastings of local wines, such as Chianti Colli Aretini. During the tour, you’ll savor typical products like extra virgin olive oil, cured meats, and pecorino cheese. Some stops include local farmhouses offering authentic culinary experiences.
Special Stop: Wine tasting at a local winery nestled among the Tuscan hills.

4. Nature Hike in the Val di Chio
Duration: 4-5 hours
Description: Perfect for nature lovers, this tour takes you through the Val di Chio, a lush area nestled in the hills of Castiglion Fiorentino. The route includes trails through woods, vineyards, and olive groves, with stops in small nearby villages like Orzale and Mammi. During the hike, you’ll enjoy stunning landscapes and spot local wildlife.
Special Stop: The panoramic viewpoint of Montecchio Vesponi, offering spectacular views of the valley and its medieval castle.

5. Castles and Fortifications Tour
Duration: 3 hours
Description: Castiglion Fiorentino boasts a rich history of military and fortified architecture. This tour includes a visit to the Castle of Montecchio Vesponi, one of the best-preserved medieval fortresses in Tuscany, and the ancient city walls. Along the way, an expert guide will explain the strategic importance of the town throughout history.
Special Stop: Montecchio Vesponi Castle, with its battlements and fascinating medieval atmosphere.

Other Activities and Experiences

• Tuscan Cooking Classes: Learn how to prepare traditional dishes like ribollita and handmade pici in an authentic local kitchen.
• Bicycle Tours: Explore the hills of Valdichiana by bike, pedaling along scenic routes and roads immersed in nature.
• Local Events and Festivals: Castiglion Fiorentino hosts traditional events throughout the year, such as the Palio dei Rioni and the Maggio Castiglionese, perfect for experiencing the local atmosphere.