Self Guided Walking Tours in Tuscany

Our first walk includes fertile valley farming, woods, vineyards and lovely stone hamlets. The views back to San Gimignano are just stunning. Much of the walk is on deserted gravel roads and linking paths. The village of San Donato is much as you would image it being many hundreds of years past except for the very modern wine and olive processing equipment tucked in behind the ancient wooden doors.

A centuries old oak tree is the marker to move from one valley to the next via the ridge top castle at Montauto. There is an almost 360 degree view of Tuscany at it best. The return to San Gimignano is via a valley complete with original mill and past the front gate of Mount Oliveto Convent with its delightful formal garden.

A ridge walk that just keeps on providing spectacular views with an historic and well preserved medieval town to explore at the end. By following old cart tracks and linking pathways, we pass by fields of durum wheat, sunflowers and corn all growing in some of the richest soil imaginable. Pretty small hamlets are dotted along the way.

High on a ridge is Colle Val d’ Elsa, the end of the walk and the beginning of exploring. The Hilltown has many well preserve medieval houses rubbing shoulders with Renaissance palazzos. Yes there was Medici money in Colle Val d’Elsa. It was and still is the crystal centre of Italy.

San Gimignano loop leaves via Porta San Matteo and follows a short section of local road before we leave it to enjoy the traditional Tuscan countryside. Very rarely, are stunning views of San Gimignano and its fabulous towers not to be seen on the horizon.

Our route takes you along cart ways, through rich agricultural farming including vines, olives, haymaking, figs and walnuts. We return via the imposing entrance of Porta San Giovanni.

San Gimignano Loop is a good walk to do on Sundays. Relaxing, wonderful views back to its imposing towers and by walking in the morning you arrive back in time to enjoy and join in the traditional Sunday promenade or passeggiata.

After a local bus ride from San Gimignano to start the walk, we suggest leaving Monteriggioni the charming fortified medieval village to explore on your return. The route takes a leisurely path through woods to reach a beautiful stone path dating back to medieval times.

The path then winds down to cultivated fields leading to Abbadia a Isola, a Cistercian abbey founded in 1001. Abbadia a Isola played an important role for pilgrims walking from France to Rome along the Via Francigena. From this point, a steady climb along a broad gravel track lined with an ancient stone fence protecting vineyards and olive groves and returning through shady woods. There is plenty of time to explore the 13C-fortified village of Monteriggioni with its fourteen towers before taking the local bus back to Sam Gimignano.

Much of this walk follows the ancient Via Francigena passing numerous historic hospices, churches, restored villages and the Santuario de Pancole. The magnificent estate of Villa del Monte is a beacon on the walk and also provides a good resting spot.

The highlight is certainly exploring Certaldo, the medieval red brick hill town accessed by a funicular. Boccaccio spent much of his live here and the museum is certainly worth a visit.

A rural walk along farm lanes, though woods and vineyards. In spring, wild flowers abound and in autumn, the bouquet of grapes is rich. This is the centre of the San Gimignano wine district, famous for Vernaccia and Sangiovese varieties of wine. You walk by the cellars of wine makers Terruzzi and Puthod and enter woods before making your way towards the village of Ulignano. The walk passes a protected truffle reserve. Great views are on offer back to Castle Ulignano.