Siena: Half-day Guided Hike to Monteriggioni

4.9 / 5

15 reviews

Activity provider: Tuscan Escapes by Papilio

Siena: Half-day Guided Hike to Monteriggioni

Activity provider: Tuscan Escapes by Papilio

From US$ 53.90 per person

Walking in Tuscany is an unforgettable experience, walk the old pilgrim's trails and be guided through the breath-taking countryside by a local and enjoy some wine as your prize!

About this activity

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Duration 4 hours
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Live tour guide


  • Revel in Tuscany's medieval past with a half-day hike from Siena
  • Enjoy the view of ancient castles and historical sites while crossing vineyards and olive groves from Siena to Monteriggioni
  • Savor local wines with a guided tasting
  • Marvel at Monteriggioni's imposing fortress
Full description
Give your mind a rest from the noise of the crowded towns, follow your expert guide on a pleasant walk along the Via Francigena, an ancient pilgrim route first plotted by the Archbishop Sigeric of Canterbury on his return from Rome in the 9th century. The route was considered the main artery to Rome throughout the Middle Ages and is still a popular trail today. Once a highway of men and emotions, a spiritual pilgrimage as well as wealthy trade route, the via Francigena had been forgotten and almost entirely relegated to history by modern roads and only recently brought back to the grip of modernity, enjoyed by many modern pilgrims and hikers alike. Experience the beauty of the mixture between the Tuscan countryside and the glory of its medieval past, still present in the wonderfully preserved castles, villages and ruins along the route.   Pass through forests and fields, vineyards and olive groves from Siena to the imposing fortress of Monteriggioni, a medieval fortress built by the Sienese in the thirteenth century as a bastion of defense in their wars against Florence, today a fortified but quaint village with many shops of local crafts and products.   Once in Monteriggioni, enjoy a guided tasting of local wines before saying goodbye to your guide. You can then remain to explore the village and the surrounding area further at your own pace or return to Siena right away, as you are given bus tickets to return to Siena in your own time (several return buses available throughout the afternoon).
  • Transport to the starting point for the tour
  • Wine tasting
  • Expert English-speaking guide
  • Return bus ticket to Siena
  • Tips and gratuities
Not suitable for
  • People with mobility impairments
  • People with low level of fitness

Select participants and date



Meeting point

Siena train station (in front of pharmacy) at 09:00am

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Important information

What to bring

  • Comfortable shoes

Not allowed

  • Luggage or large bags

Know before you go

  • This tour is suitable for anyone in good physical condition and with experience in long walks
  • appropriate and comfortable clothing and shoes are a must, as is water (hat and sunscreen in summer and rain jacket in winter are recommended)
Customer reviews

Overall rating

4.9 /5

based on 15 reviews

Review summary

  • Guide
  • Transportation
  • Service
  • Organization

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I had such a beautiful hike with Keko and the other travellers. Keko has a really passion for Siena and the land, and it was a true gift to learn from him about the pilgrimage and how to take care of the land through his and his community’s farming practice, and how this impacts our overall health. I would recommend this tour to anyone who has a love for nature and being in the outdoors! I hope everyone has the pleasure of meeting Keko and sharing in this unique and special experience. Grazie mille Keko!

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March 27, 2023

Yesterday’s hike from Siena to Monteriggione was spectacular. More than I expected. Keko was an incredibly excellent guide. He was kind, helpful and very fun. He shared the complete history of the Via Francigena, which I found very interesting! He then as the hike continued, imparted his knowledge of the plants along the way, taking his time to show us, have us smell, taste and experience the land. He is of the area and also made us feel at home greeting the neighbors with grace and aloha. He left us in the quaint and historic village of Monteriggione in hands of Stefano and darling Margarita to taste wines paired with local cheeses and fresh olive oil. Stellar 5 star tour! I would do it again tomorrow if it were availabile. Obviously I highly recommend this tour. Aloha, Susi

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March 27, 2023

Great 3 hour morning hike with personable and naturalist oriented guide. Lovely lovely scenery. We would have preferred a bit more background on the Via Francigena. Winery to end with was great - we bought the winery’s artisan cheese to go along with the bread and Chianti. Overall, an excellent experience and great value!

March 27, 2023

Product ID: 49693