It's not easy to choose only a few things to visit in Maremma as it's a vast area tucked away in southwestern Tuscany.
It was hard not to include incredible places like Castiglione della Pescaia, a fishing village clinging to the Petriccio hill and associated with the 14/15th century fortress, and Populonia, in the Gulf of Baratti, known as the main outlet to the Etruria Sea in the 4th/3th centuries BCE. The truth is, you shouldn't try to do too much if you only have a short break, or you'll simply miss the spirit of Maremma. Live slowly, enjoy each moment, appreciate the simple things in life, talk to people, make new friends.
For the "3 towns in Maremma" tour, rent a car so you can stop every time you want to take a picture, visit something totally unplanned and, most of all, just take your time. This itinerary is a great option at any time of the year.
The walls around the historic center of Grosseto were erected in the last fifteen years of the 16th century, encapsulating older medieval structures. Within the walls is the Archaeological Museum, which narrates the colonization of the Maremma from the Etruscan to the Middle Ages. The highest artistic achievement of the city is the late 13th-century painted cross in the Church of San Francesco, perhaps attributable to Duccio di Buoninsegna. Grosseto is the largest town in the area and you could use it as a base.
If you're curious about past civilizations and how humans used to live you shouldn't miss a visit to the Archaeological Park of Vetulonia. Only 20km away from Grosseto, in the Maremma hills you'll find one of the greatest centers of Southern Etruria, vital from the 8th century BCE to the late Roman age. What now remains is a vast necropolis traversed by the so-called Via dei Sepolcri, along which stand the artificial barrows of Pietrera and the Diavolino, dating from the 7th century BCE. The former, a hillock about 60 meters in diameter, contains two superimposed tombs dug out of it, preceded by long corridors.
One of Tuscany's picture-postcard locations, Pitigliano stands high on a cliff overlooking the rivers Lente and Meleta. In the past, Pitigliano belonged to the Orsini family, who elected it capital of their county and reorganized its fortifications in a new citadel centered around the court palace. Don't miss the dramatic aqueduct with two colossal arches flanked by 13 smaller ones from the time of the Lorraine family created by Antonio Sangallo. The center of Pitigliano is occupied in part by the ancient Jewish ghetto, the site of a flourishing community that in the late 16th century erected a synagogue, recently restored and open to the public. From Pitigliano you could also visit Saturnia and Le Vie Cave.