A Charming and Super Sweet Tuscan Town called Monticchiello

It’s a pure joy and delight to loose yourself in Tuscany.  A region where cypress trees follows you along the little Tuscan roads.  Where rolling hills seems never ending and the surprise of little Tuscan towns positioned high on hills is the norm.

It was an easy decision to hire a car and to plan a Italian roadtrip through Tuscany.  It was a harder decision to decide on which places to visit in Tuscany, when we were extremely limited in time.  We planned a full action day of driving from town to town.  Out of all our stops, it was the town of Monticchiello,Italy that took my breathe away!  A lesser-known town in the Orca Valley; a hop and skip away from the more well known Pienza.

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A Charming and Super Sweet Tuscan Town called Monticchiello

Monticchiello, happens to be one of the cutest towns in Tuscany.  It is surrounded by what remains of the ancient town walls.  The entrance to this town is through the impressive Porta Sant’Agata.  This gateway is accompanied by the remains of two defending towers on each side.  Interestingly when we arrived at this town, one of the occupants were practising their ‘drumming’, it was quite bizarre looking up the ancient  ‘castle-like’ exterior structure of the town whilst listening to modern drumming coming from somewhere inside.

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This little Tuscan town is filled with charm and is just incredibly as sweet as can be.  Whilst it won’t take you long to explore the grounds of this gorgeous medieval Tuscan Town, you will find heaps of picturesque photo opportunities.  Loads of little gorgeous details lining the rugged stone walls of the buildings inside.  The pride from the residence oozes here in a town that is incredibly well looked after.

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Regardless of Montichiello’s small size, right in the middle of this gorgeous little town, you will find the town church – the Church of Santi Leonardo and Cristoforo, dating back to the second half of the thirteenth century.

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Another reason to visit Monticchiello is simply because of the stunning views you get over the Orca Valley.  On your way out of this little town, before you leave through the gateway arch, climb the stairs next to Osteria la Porta Tavern and you will find yourself on top of the remains of the wall that surrounds this charming little town.  And from here, you can get some magnificent views over Tuscan valleys as well as other Tuscany towns.

Stay here a while and just soak in the beautiful Tuscan picture in front of your eyes.  Look to the right for an amazing view over Pienza in the distance.  It simply doesn’t get much better than this!!

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And lastly, before you get back in that car, make sure you pop into the Wine Bar located at the front of Monticchiello.  After all you can simply not visit Tuscany and not enjoy the multitude of wine tasting opportunities that come your way.  Why not pop into Wine & Food La Guardiola and give their food and wine a try.

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One of the beauties of this little town is that it is very much untouched by tourism.  I think that we were some of the very few tourists who wondered down the streets of this town on our visit.  It was just incredibly peaceful and the atmosphere you find here is sure to relax and unwind your soul.  The perfect place to not only ‘loose’ yourself but also to ‘find’ the essence of you are.



Do yourself a favour and pop this little walled Tuscan City: Monticchiello on your ‘HAVE TO SEE’ list.  You won’t regret it!!!

Say NO to the demands of the world.
Say YES to the longings of your own heart.
– J Huie [Tweet This]

and find your heart and soul here in Monticchiello.


Over to you, which town in Tuscany is your absolute favourite??



Monticchiello Tuscany Italy

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  • Reply
    July 4, 2015 at 1:11 am

    Ciao Jolene i’m Francesco i write you from Monticchiello 🙂 I am a true resident of Monticchiello. “un vero Monticchiellese”
    I want to thank you for the wonderful article that you published about my country, I will share it immediately on my facebook page.
    I am the owner of B & B La casa di Adelina and of Wine & Food La Guardiola, if you decide to return to Val d’Orcia advise me that I will be happy to meet you.
    If you want, but only if you want, you can include in your article the names of Guardiola and the B & B La casa di Adelina so as to leave a little more information to your readers

    here are our addresses:

    Thanks again soon
    greetings from Monticchiello.

    • Jolene Ejmont
      Jolene Ejmont
      July 4, 2015 at 11:38 pm

      Hi Francesco and thank you for your lovely comment! We truly did love Monticchiello and hopefully we can return one day. Would be lovely to meet to you 🙂 Your B&B looks delightful, will include it for you (just heading out for date night with hubby first). We would love for you to share the post with your followers on Facebook. I have ‘liked’ your page as well 🙂 We are also on Facebook –
      Greetings from Australia 🙂

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