There are severals artistic and gastronomic journeys to enjoy the beautiful tuscan countryside. From Poggibonsi start noumerous beautiful biking and trekking paths .

Staggia senese- it is a very important castel along one of the Francigena route's traces in Valdelsa. It has been contended for a long time and, because of its alleance with Siena, it has been destroyed later from the Florentine militias. At the end of 13th century the Franzesi family bought it. During the 14th century the castle has been rebuilt and in 1361 the city of Florence bought it. Mainly It keeps intact its medieval structure. The sourronding wall is alternated with severals polygonal towers. There were originally three entrances of which two are still visible, the North-East door and the Florentine door; while the Senese door has disappeared. The castel, with its irregular plant is being renovated.

The ancient S. Maria Church has been completely renovated in 1800. In the nearby museum you can contemplate the “S. Maria Egiziaca” picture and some interesting boards of Sienese and Florentine school of the 14th and 15th century. The museum is collocated in Grazzini square next to the Santa Maria Assunta in Staggia, phone 0577 930901, open on Saturday, between 4,00 p.m. and 5,30 p.m, from April till October.

Castello di Strozzavolpe- castle of the 12th century, built by the Guidi conts, it has mainly kept the original aspect because of this it is possible to enjoy its ancient medieval structure. In accordance with the legend a fox tried to impede the construction of the castle, for this reason the animal has been hanged and gold-filled to wish the castle a very long life. it's worth to visit the sala d'arme and the noble chapel of S. Martino modified during the Renaissance.

Around Poggibonsi there are many church which it's worth to be visited.

Chiesa di S. Andrea a Papaiano- dated at 1100, where there is a fresco of the Florentine school, "Madonna col Bambino e Santi" dated at 1492 (perhaps work of Filippo d'Antonio Filippelli) and a the Sacra Famiglia dated 1700. The apse show three authentic monoforas.

Chiesa di S. Maria a Talciona- dated at 1100 and modified in 1200, it has only one nave. it's worth to be visited, above all to see the apse and the epistyle of the portal which has a bas-relief dated 1234 where is illustrated the "Adorazione dei Magi". The architrave is supported by shelfs on which there are fantastic zoomorphic pictures. There is also a terra cotta polychrome tabernacle which has been attributed to Giovanni and Andrea della Robbia.

S. Pietro a Cedda - consitued one of the more beautiful example of romanic art in Valdelsa. It has only one nave, one apse and many beautiful stone romanic ornaments; there is also a tabernacle of Mino da Fiesole school. The Florentine school triptych dated at 1300 of this church is exposed to the art museum of Colle Val d'Elsa from severals years.

S. Donato in Gavignano

S. Pietro Church in Canonica

S. Martino Church in Luco

S. Bartolomeo Church in Pini

Magione di Torri Ex Magione of the Cavalieri of Malta on the Francigena road, dated at the first decade of 1000.