Run and Wine Experience

A beautiful run through the vineyards

Join me for a run through the beautiful and natural calming vineyards of Montepulciano. Every day I go running in this wonderful Tuscan landscape. Running through the vineyards is an unforgettable experience!

The run and wine is about 5 km running on road and trail with frequent stops to take pictures.We don’t track running time, but participants should be able to run or walk at least 3 km.

About this activity

  • Duration 2 hours
  • Suitable for everybody
  • Certified sommelier (Italian, English, Dutch speaking)
  • Experienced runner
  • Wine surprise
  • Free cancellation up to 12 hours before the activity starts


The start is at the 16th century San Biagio church. From the church there are splendid views over the surrounding valley.

The route passes by some important Montepulciano sites. The trail is challenging with running up and down hills several times. 

There’s a short run back uphill through the countryside. The last part is quite steep. We run again on asphalt towards Montepulciano.

When we are at the historical centre we can decide whether to stop for coffee in a local bar or continue our way.

Now we arrive at the other part of the town. The asphalt road ends here and the route continues into the vineyards. Enjoy the sounds of nature and the amazing views over the gentle landscape.

It can very well happen that we see a deer or a wild boar running across the vineyards.

The route continues into the vineyards with spectacular views. This road brings us back to the starting point at the San Biagio church. 

Time to take a refreshment! Water and fresh seasonal fruit are available here and … a wine surprise!


  • Drinks and fresh fruit
  • Wine surprise

Prepare for the Experience

Important information

As a run leader I recommend every participant to wear proper sport shoes and suitable clothing.

The Run and Wine experience is safe, and in case of emergency I always carry my mobile phone with me. Participants are asked to respect the rules of the Run Experience.

In case of rain wear water-resistant clothes. It’s important to stay dry as long as possible.

Meeting point is at the San Biagio church: Via di S. Biagio 14, 53045 Montepulciano (SI).

Google maps: 43.090872, 11.774649

Please note that the trail of the Run and Wine Experience is not flat. You can only participate if you are able to walk at least 3 km.


The price is 20 Euro per person.

Solo travellers are welcome. You can book a private Run and Wine Experience for one person without extra charge.

Run and Wine Experience

Free cancellation

It is possible to cancel your booking up to 12 hours before the start time. You can decide whether to get a refund or to move the experience to another date (upon availability).


June 13, 2019

Sylvia and the run and wine experience was just lovely – a unique and amazing way to explore the tuscan landscape whilst getting active. We stumbled across this experience on Air Bnb and were immediately interested as my partner and I (Australians) like to keep fit when on holiday – to balance all the wine and pasta! The run is suitable for all levels – my partner (a keen runner) ran off at times and I would stop and walk (and Sylvia would walk with me). The best part about the run/walk was meeting Sylvia, who has lived in Italy for 10+ years and spoke to us about the history and gave us winery tips – but most of all has a lovely personality and it was a pleasure being in her company! I would highly recommend this experience to anyone visiting Montepulciano.

Nikki (Australia)

July 14, 2019

Amazing experience. I’m a holiday runner (to stay fit) and the run was amazing and Sylvia adapted it to my level as well as interest in Montepulciano and the vineyards. Sylvia has a passion for the region, its history and culture and importantly, for sharing that with you. I highly recommend this run or walk with Sylvia – a unique experience in a unique part of the world.

Mike (Belgium)