Siena: Half-day Guided Hike to Monteriggioni

4.8 / 5

12 reviews

Activity provider: Tuscan Escapes by Papilio

Siena: Half-day Guided Hike to Monteriggioni

Activity provider: Tuscan Escapes by Papilio

From US$ 43.81 per person

Walking in Tuscany is an unforgettable experience in this historically rich area where nature is in perfect harmony with mankind and the past is still surprisingly present. Be guided through the breathtaking coutryside on a half-day hiking tour.

About this activity

Free cancellation
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Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details. Learn more
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 organic 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 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 it's 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.  Once in Monteriggioni, 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 bus ticket to return to Siena.
  • 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
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask

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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
  • It is highly recommended you wear comfortable clothes and shoes, to bring water, a hat, and sunscreen
  • The normal operation of the activity is subject to weather condition
  • In case the tour has to be cancelled due to adverse weather conditions, the choice of a tour on an alternate date or a full refund will be offered
Customer reviews

Overall rating

4.8 /5

based on 12 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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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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September 20, 2022

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!

May 30, 2022

A wonderful tour! We had a lot of fun and joy with our guide Kiko. Kiko went to great lengths to bring the country and the people closer to us. It was very exciting to learn things from the past and from the present time. Wild herbs along our hike on the pilgrimage route and anecdotes from the past made the hike very entertaining. The path was very pleasant to walk. In Monteriggioni we had a very nice wine tasting. We really liked the wine, so we even ordered delivery to our home. Afterwards we had a very good meal in the nice little place. We would have loved to have stayed there. I highly recommend this tour! Thank you dear Kiko!

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April 14, 2022

Product ID: 49693