Siena to Monteriggioni: Hiking the Via Francigena & Wine Tasting in Tuscany

What is it about Tuscany that makes so many of us dream?

(This isn’t even a rhetorical question, I would actually love to know in the comments!)

I got to take a dream trip to Tuscany with three of my cousins this summer. If you’re planning on visiting Tuscany in the future or anytime soon, I wanted to share one of our favorite activities that I highly recommend you add to your itinerary: hiking the Via Francigena from Siena to Monteriggioni followed by a wine tasting of local organic Chianti with Ciao Florence (not sponsored, but highly recommended!). The Via Francigena is a pilgrim trail that goes all the way from Canterbury, England to Rome , and people still use it to this day!

I honestly thought that one of my cousins would never ever get on a transatlantic flight, and therefore never visit Italy. It still brings tears to my eyes that she faced her fear of flying, got on that flight, and now we have amazing memories together in Italy (and another trip in the works!). This hiking tour was the highlight of our time in Tuscany, and I highly recommend this tour if you enjoy getting out in nature! Everything about this tour was fabulous, from our guide, to the scenery & wine tasting.

I took a little video footage of our hike, although I had NO idea what I was doing with the camera! Since then, I have been learning about filming & editing, and it has become one of my (many) passions. I hope that next time I can really do Tuscany justice through film. In the meantime, enjoy my little video with some new Italian phrases I learned, and my photo montage of our Tuscan hike.

Ciao Florence Hike & Wine Tasting Siena to Monteriggioni
The start of our hike, just outside Siena. The cool, overcast weather was perfect for hiking.
Poppies in Tuscany
We hiked amongst fields of vibrant orange poppies.
castle in Tuscany
We passed by several castles amongst olive groves along our hike on the Via Francigena on the way to Monteriggioni.
Via Francigena hike Tuscany
Hiking is the best way to enjoy the peaceful Tuscan countryside.
Hiking in Tuscany with Ciao Florence Tours
We hiked for four hours along the Via Francigena from Siena to the little hilltop town of Monteriggioni.
Flowers in Tuscany
Our guide told us about the traditional medicinal uses of many Tuscan flowers & herbs.
Via Francigena Tuscany
A signpost for the Via Francigena, a pilgrim trail that goes from Canterbury, England to Rome.
Palio Horse in Tuscany
We got to see some of the Palio horses along our hike!
Ciao Florence Siena to Monteriggioni hike
I stopped to smell the roses!
Organic vineyards Tuscany
We walked right by some Chianti vineyards on our hike/wine tasting tour with Ciao Florence!
Cyprus trees Tuscany
This is my kind of exercise with views like this!
Via Francigena passing through Monteriggioni
The Via Francigena passing by Monteriggioni.
Monteriggioni, Tuscany, Italy
Arriving in Monteriggioni after 4 hours of hiking!
Monteriggioni, Tuscany, Italy
Monteriggioni is a tiny walled hilltop village in Tuscany.
Monteriggioni restaurant
Monteriggioni is tiny, yet oh so quaint and charming!

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Food for Thought:

What three adjectives would you use to describe Tuscany?

What is it about Tuscany that makes you dream of visiting there?

Hi, I'm Kelly!

I invite you to join me as I document becoming a dual U.S.-Italian citizen, my travels in Italy to discover the best of regional food & wine, and my progress learning Italian, mostly through cooking & wine tasting!

WSET Level 2 Certified Wine Blogger

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a mindful traveler

So rustic, I love the authenticity of this region. Xx

Christina Conte

First of all, you did a great job with the video! Loved it! Your photos are phenomenal and I can’t believe I’ve never heard of this trail! Canterbury to Rome! OMG, how cool would that be? Thanks for the post, so happy I learned something new!