Half day Guided Hike to Monteriggioni & Wine Tasting

A medieval walk in nature


Your meeting point for the start of the tour is from the Siena train station (in front of pharmacy) at 9:00am

Give your mind a peaceful rest from the noise of the crowded towns, follow your expert guide on a pleasant walk along the Via Francigena, an ancient pilgrim route for the first time plotted down by the Arcbishop ‘Sigeric the serious’ of Cantebury on his return from Rome in the 9th century and considered the main artery to Rome throughout the middle ages.

This route, that has for centuries been a highway of men and emotions, a spiritual pilgrimage and a wealthy trade route, has been forgotten and almost entirely relegated to history by the modern paved car roads. Only recently the route has been brought back from the grip of modernity and is today enjoyed by many pilgrims and hikers alike. Experience the beauty of the mixture between the Tuscan countryside and the glory of its medieval past, still present in its wonderfully preserved castles, villages and ruins.

See the Tuscany you would never want to miss before returning home, pass through forests and fields, vineyards and olive groves from Siena to the imposing fortress of Monteriggioni. A medieval walled town located on a natural hillock, built by the Sienese in the thirteenth century as a bastion of defense in their wars against Florence. It withstood many attacks from both the Florentines and the forces of the Bishop of Volterra until in an act of reconciliation with the Medicis, the town’s captain simply handed the keys of the town over to the Medicean forces - considered a "great betrayal" by the town's people. Once in Monteriggioni, you will enjoy a guided tasting of local organic wines before saying goodbye to your guide for the end of the tour. Feel free to explore the village and the surrounding area at your own pace. You will be given a train ticket to return to Siena railway station. Trains leave on the hour (every hour) and can be taken at whatever time you prefer from the nearby station. The tour starts in front of the Pharmacy outside of the Siena Train station on Monday and Thursday mornings, with pick up at 09:00am from in front of the Pharmacy.

The hiking tour is suitable for anyone in good physical condition and with experience in long walks. It is highly recommended you wear comfortable clothes and shoes, to bring water, a hat, sun cream.

The normal operation of the activity is subjected to weather condition. In case the tour has to be cancelled due to adverse weather conditions, we will offer the choice to tour on an alternate date or receive full refund.

Have a look at our Activities Calendar to see what tours are running during your stay in Tuscany!


  • Company of Expert local guide
  • Walk through hiking trails and countryside paths with no vehicular traffic
  • Guided organic wine tasting
  • Visit Castles and historical sites and cross vineyards and olive groves


  • Transport to starting point for the tour
  • Expert English speaking guide
  • Return public transport ticket to Siena
  • Map with Bus times and directions for return to Siena

Tour details

  • Duration: 4.0 hours
  • Start time: 9:00am
  • Price per adult from: 45.00€


Monday 9:00am to 12:00am Thursday 9:00am to 12:00am