Grosseto, our capital, is just 23 Km from Castiglione towards the south. It is one of the few capitals whose old town is completely surrounded by a massive sixteenth-century walls,  it is well worth a visit the Duomo and Palazzo Aldobrandeschi in Piazza Dante, the Cassero of the Salt situated in Piazza del Sale, the Archaeological Museum and several churches. A few kilometers from Grosseto, in the direction of Siena, we find the important archaeological site of Roselle ancient Etruscan/Roman town, the site requires at least three hours for a visit. Continuing towards the south we get to Alberese, entry point of the Maremma Natural Park or Park of Uccellina, Here nature lovers will have the opportunity to go hiking in the Mediterranean brushwood , the park is home of numerous colonies of water birds and fauna of the area, in the grasslands at the bottom of the mountains of Uccellina grazing Maremman cows and Maremman horses. Still in a southerly direction at 64 km approximately from Castiglione are located at the center of one lagoon is Orbetello. The lagoon is crossed by a road that runs through the entire length and leads to the Argentario promontory, a famous tourist destination due to  its beautiful views and seaside villages like Porto Santo Stefano, which is the main town and offers connections with the islands of Giglio and Giannutri and Porto Ercole, which is among the most beautiful villages in Italy with its four forts, of which the most visited is Forte Stella with a six-pointed star-shape. A little further south along the highway towards Rome (63 km from Castiglione) at the Ansedonia exit, following the signs, we find the Etruscan - Roman archaeological site of Cosa, situated on a promontory, the show that can be enjoyed from here on tombolos of Feniglia and Giannella, which connex the mainland to the Argentario, is unmatched. Just 40 kilometers to the south, in Montalto di Castro, there are Vulci , a very rich archaeological site for it's remains and ruins, famous for the tomb of Francois and his unique environment that blends the pastures reserved at Maremmane cows with archeology in an ideal environment for long walks and picnics. Continuing south, now in Lazio region but still close enough for a day visit, we find Tarquinia, known for its funerary frescoes dating back to the seventh century BC. Among Ansedonia and Montalto di Castro, at Pescia Fiorentina in the municipality of Capalbio is a famous theme park, the Tarot Garden , where they represented  twenty-two tarot cards in cyclopean sculptures made of famous artist Niki de Saint Phalle.

On our way inwards  we find many are medieval towns, let's start with the Tufo area. The territory is characterized by fascinating rock settlements, villages and medieval fortifications which arise nearby of major population centers of the Etruscan-Roman period. Pitigliano by car, is almost two hours from Castiglione (103 km). It is a typical village of Maremma, unique for being built entirely on tufa rock. Sorano is just 9 km from Pitigliano, a rare jewel of medieval town planning, and the small Sovana 7 km, a charming village with an atmosphere of being frozen in time. At the end of the visit of these three villages we recommend a relaxing bath in the sulphurous waters of Terme di Saturnia that are nearby, you can enjoy the thermal waters is a SPA, or  freely outdoors in the beautiful Cascate del Mulino . Along the two roads to reach Pitigliano will cross Magliano in Tuscany, a charming medieval town is surrounded by sturdy walls running along the top where you can stop to enjoy beautiful views, or Scansano is known for its production of fine wine. Just one hour from Pitigliano you can even reach Orvieto, where down the road you can see the Lake of Bolsena. If you go to Siena, you can not miss the opportunity to visit the tiny Monteriggioni surrounded by its walls, just a twenty minute drive from Siena toward Florence. As well as San Gimignano , an important medieval town renowned for its numerous towers. Now, to return to our base you can continue the road towards Cecina and along the way visit Volterra , the acropolis where there are the foundations of two temples and medieval buildings like the Cathedral, the Medici Fortress and Palazzo dei Priori on the homonym square, the city preserves a remarkable historical center of Etruscan origin. On the main road that connects Grosseto to Siena, about half an hour from the  capital, it is important to note Petriolo  where you can enjoy sulphurous thermal waters at a SPA, or  freely outdoors. The most popular of inland tours, because of its wonderful villages and local products, is that of Montepulciano, which is a 1:50 hour drive (116 km from Castiglione) and Montalcino , their famous wines need no introduction; Pienza for its many shops where you can buy high quality of Pecorino chesse at good price; San Quirico, another charming medieval village and the small Bagno Vignoni , where an ancient thermal pool replaces the town square and there are high-level spas as well as  free hot springs. A religious itinerary can not miss the Abbey of S. Antimo just 9 km from Montalcino, an ancient monastery surrounded by greenery that was an important stage of the Via Francigena; completely different in architecture is the Abbey of Monte Oliveto Maggiore, located between Montepulciano and Buonconvento is less than a 2-hour drive (100 km) from our base point, inhabited by Benedictine Olivetani monks famous for the production of officinal products; and, finally, the abbey of San Galgano , Gothic style, dating from 1218 AD is famous for the legendary Sword in the Rock, still in the Siena area,  a 1-hour drive from Castiglione where you will find theater performances and operas during the summer months. The Monte Amiata area is approx 80 km from Castiglione if you start your tour from Castel del Piano, among the various villages of the mountain, worthy mentioning is that of Santa Fiora which houses a  large and ancient fishpond in a park planted with trees; in Seggiano , also in the area, you can visit The Garden of Daniel Spoerri a path through 15 hectares of green, full of works of art.