Armaiolo is a quaint village in Rapolano Terme, crossed by numerous trails. The earliest historical records referencing the village date back to 1260, when the Florentines, defeated by the Sienese at Monteaperti, damaged the Castello di Armaiolo.
In 1524, the Armaiolo people opposed the Duke of Albania, sent by the King of France. For this affront, they were killed. Yet the most devastating tragedy dates back to the last war between Siena and Florence. On May 30, 1554, the castle was besieged by the Imperial-Medicean Army. Inhabitants were ordered to surrender but when they refused, all the men were killed and the Armaiolo Castle was set on fire.
Also linked to Armaiolo is the tale of a Sienese notary, Cristofano di Gano di Guidino, who served several times as Vicar of the Municipality of Siena. Cristofano had a strong friendship with Catherine Benincasa (now known as Saint Catherine of Siena), the Patron Saint of Europe who, according to legend, would stop by Armaiolo.
The village, overlooked on either side by its stone towers, is divided into an interweaving of narrow alleys. The castle is then divided into thirds—the Campana, Fontebranda and Finimondo. To reach Finimondo, the terrain is steep and pebbly, being difficult to navigate even on foot. The stones, mixed with the travertine and bricks that comprised the masonry and the remnants of this ancient road that led to the village of Armaiola, are sharp and pointy.
The small hamlet is headed by a number of routes through dense wooded areas in the northern part of the municipal area, where the cottages of Castiglioni, Campiglia, built in the 12ᵗʰ and 13ᵗʰ centuries, are located. Monuments of interest include the Church of San Biagio, a single-nave Romanesque-style building, along with the Church of San Giovanni.
