Gaiole: From its origins and more clearly in the XIVth C. Gaiole was an important centre for commercial exchanges. Situated between Florence and Siena it was often victim of assaults till the 1555 when Siena lost against Florence. Later on in 1776 it became a town hall. The territory is rich of castles like Brolio owned by the Ricasoli family as well as Cacchiano. The last one was destroyed by the Aragonesi in 1478 and rebuilt in 1530; Monteluco made of 2 buildings and located on top of a very panoramic hill. Worth visiting are Pieve S. Polo in Rosso, Pieve S. Giusto in Salcio, Meleto Castle and much more.
* Parish of St Marcellino
It is characterized by a hut facade, in "alberese" stone. The apse decorated by a single window, it is te only primitive settlement. The the size of tune with those of other smaller parties to the church, probably rebuilt during XIII.
* Parish of St Polo in Rosso, XII secolo.
The name of the church it is in a donation of 1070 and is cited as "Sancti Pauli scito Russo". Even in the "bubble" dated 11 March 1103 issued by Pasquale II to the Bishop Giovanni da Fiesole, there are are notices about this parish. Remarkable.
* Parish of San Giusto in Salcio
In romanic structure and design, it was rebuilt bewteen the 1926 and the 1929.
* Parish of St Mary a Spaltenna
Dates back to 1030. It was transferred the parish church of San Pietro in Avenan (1102-1110), which was renamed in Santa Maria a Spaltenna and transformed into church 'munità. Definitively renamed by the Bishop of Fiesole in 1153 with its current name..
* Parish of St Bartolomeo a Vertine
Two of his works are now in the main gallery of Siena: Our Lady of Advisors, a work of youth Simone Martini, and the triptych of Bicci Lorenzo depicting the 'Madonna with Child and Saints Bartolomeo, Giovanni Evangelista, Maddalena and Antonio abbot (1430)
* Parish of St Vincenti
n the seventh century his name was Basilica Sancti Vincenti in fundo Bomuspagi.
* Church of St Lorenzo ad Ama
The territory of the church is mentioned in some of the scrolls in Vallombrosa Abbey and the Abbey of Coltibuono in the twelfth century and the thirteenth century and it was owned of Ricasoli since 1100.
* Church of St Sano
It is dedicated to the Christian martyr Ansano, part the roman Anicia family, beheaded in 303 by order of proconsul Lisia.
* Canonica di St Lorenzo a Mello
Inside it has a nave without apse and a transverse arch, that divides the area from presbyterial to the rectory. At a side of the arch, there are two zoomorphous heads. One of them is a pedal representing a little bull.
* Church of St Pietro in Avenano
Comes from bevore the 1000 year and it's known as parish from the XI-XII century.
* Oratorio dei Pianigiani
On the back of Oratory wall, it is painted "the Madonna Enthroned", surrounded by angels and saints, with the child in her arms: Child takes a little bird in the left hand and a precious stone in the right, a symbol of the Good News. To the right of the Madonna is the fresco depicting "St. Michael Archangel" that tramples the dragon and weighs souls. On the other side St Francesco with the Rule in his left hand, a crucifix in his right hand and the stigmata feet and hands. The two side walls are figures of saints: St. Anthony Abbot, represented with belt piglet - over this fresco there is a opened a crack - St. Lucy, with the inscription "S.ca Lucia", which shows the symbols of his martyrdom. St Johannes Bapist, bearing the inscription: "Ecce Agnus Dei", St. Peter with a book in hand, St. Luke the Evangelist with the inscription: "S.co Lucha Vangelista". Behind St Luke, there is the name of outsourcer (Luke Canpoli). The fresco of St 'Mary Magdalenà is very deteriorated from a leak, with the inscription: 'M. S.ca Magdalene' and a date (also deteriorated): 1496