In Roman times and the Middle Ages, there are explicit references to this migratory phenomenon in vast areas including central Italy.

From the first half of the 13th century, when the Republic of Siena decided on the systematic occupation of the Maremma territory, the vast uncultivated spaces used for grazing were already being utilized by shepherds from central Italy in an unregulated manner.
From the mid-14th century (1353), Siena reorganized pasture management by establishing the Dogana (Public Collection Office), a monopoly managing Maremman pastures. Some officials of this Dogana even went to Casentino in August to make agreements with the already numerous shepherds. From this moment, Transhumance from central Italy to Maremma became a mass phenomenon. The Republic of Siena understood the economic significance of regulating this phenomenon within its jurisdictional territory. Notably, the proceeds from transhumance contributed to the establishment of the Monte dei Paschi di Siena bank in 1472.

Shepherds arrived in Maremma from Parma, Reggio Emilia, Modena, Bologna, Tuscany’s Romagna, the entire Tuscan Apennines, Mugello, Valtiberina, Casentino, Umbria, Marche, and partly from Abruzzo. These shepherds used ancient routes, well-known, traversing three major “corridors” across Tuscany.
The Republic of Siena approved, in 1419, the Statute of the Dogana dei Paschi (Italy’s oldest), regulating the lives, including judicial aspects, of numerous shepherds from central Italy. The Maremman pastures, managed by this monopoly, covered approximately 110,000 hectares, with natural produce such as grass, leaves, and acorns belonging to the Republic of Siena, not the landowner.

In exchange for a fee (called “fida”), proportional to the livestock quantity and type, the Dogana dei Paschi offered pastures and guarantees to the “Vergaio” or livestock breeders (called “fidati”). The people accompanying the livestock (one adult per approximately 100 sheep) were hierarchically identified as Vergaio, Buttero, Caciere, Pastori, Bagaglioni, Montonaio, Agnellaio, Cavallaio, and Bescini. They lived in a small village near the herds for shelter, but they had to move periodically as pasture use was divided into 4 periods.

Until the Grand Duchy of Tuscany was established, which later took over this monopoly with some adjustments in 1572, there was no regulation of the roads used for animal movements from central Italy to Maremma due to political geography. During this period, everything relied on established millennia-old tradition and various communities whose territories were crossed by livestock flows (some charged tolls).
During the grand ducal period, the customs routes (sometimes with two uncultivated side strips, true livestock tracks over 90 meters wide) had to pass through specific points for fiscal checks. Shepherds from upper Casentino were checked at Ponte a Rignano; those from middle Casentino, along with colleagues from upper Valtiberina and Tuscan Romagna, whose main road passed through Talla-Passo della Crocina, were inspected at Ponte a Romito; those from lower Casentino, Valtiberina, Umbria, and Marche were checked at Ciggiano.
The three major “corridors” used for flock movements from central Italy to Maremma crossed Tuscany and arrived in the Dogana territory in three distinct areas:

1. The northern corridor reached the 1st Head or Montemassi – Massa Marittima. Reserved for shepherds from northern Tuscany, Emilia Romagna up to Bologna.
2. The central corridor reached the 2nd Head or Paganico. Used by shepherds from Casentino, Mugello, Valdarno Aretino and Florentino, and Valtiberina.
3. The southernmost corridor reached Cinigiano. Used by shepherds from Tuscan Romagna, Marche, Umbria, and part of Abruzzo.

The number of transhumant livestock in Maremma, in the pre-grand ducal and grand ducal periods, varied greatly from a minimum of around 100,000 to a maximum of 500,000 heads, of which approximately (90-95)% were sheep. About 30% came from Casentino, with peaks of around 100,000, making it one of the most important pastoral districts in central Italy.

Grand Duke Pietro Leopoldo issued the Motuproprio (11/4/1778) abolishing the Dogana dei Paschi: from the following September, this monopoly ceased to exist! From this point, shepherds had full freedom to use all roads without any toll or other previously imposed burden. The costs of pastures, now in the hands of true private owners, increased, and only shepherds with medium to large farms (alone or in “Sortarie”) continued this practice, but few took advantage of tax incentives for land acquisition.

The smaller shepherds, at least from upper Casentino and from the early 19th century, saw that it was not profitable to continue moving to Maremma. They found other outlets for their transhumance in smaller and closer territorial areas, such as the agricultural estates near Florence, where they settled in Soccida. Some of these, in the early 20th century, returned to Maremma.

The Maremman Transhumance, which until the mid-19th century was a predominantly male phenomenon, lasted until World War II, and with the agricultural reform of the early 1950s, this millennia-old practice, as old as humankind, ceased to exist!