Our Favorite Tuscan Hill Town (Monticchiello) and Region

Our Favorite Tuscan Hill Town (Monticchiello) and Region

When we fell in love with Santa Margherita & the coast of Ligure, we were uncertain if we would fall as deep in love with Tuscany. With expectations so high … maybe it would not be all that we were hoping…

I cannot speak for every walled hill town in Tuscany, but for us Monticchiello was out of a Tuscan dream! Situated at the top of a hill (like all hill towns in Tuscany), you drive up a windy road lined with olive trees to find the charming walled city.


We stayed at the most beautiful 2 bedroom fully equipped apartment called La Cocca, which is owned by a B&B in town La Casa di Adelina. These are both owned by Francesco, who will cook you up the yummiest breakfast of eggs (many styles!), home cooked breads and hot cappuccinos!  He was even so kind as to arrange a cooking class for us to learn to make the local pasta specialty of pici. Check out the post and step by step recipe here for Homemade Pici Pasta.


Local art among olive tree gardens . . . open to the public and all right out our doorstep.IMG_3232

The town is very small (90 residents), but has delicious restaurants, friendly locals, gorgeous views and is close enough to the action to easily explore places like Bagni San Filipe, Montepulciano, Pienza, Cortona and Siena (to name a few).IMG_3217

The hot springs of Bagni San Filipe (just a 30 minute drive).IMG_3128 IMG_3123

Olive trees, churches and views from the surrounding towns of Montepulciano, Pienza & Cortona…IMG_3168 IMG_3163

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As for restaurants in Monticchiello …

Traditionally in Italy , shops will close for siesta – usually between 1-3:30pm. Dinner restaurants will not open until around 7:30pm, so often times were say waiting as we went too early.  For us, a way to save money and not waste food was to share our meals.  Order a salad and a primi piatti. If you order wine or beer, it is customary in most restaurants in Tuscany to also bring you some snacks like breads, olives, salami or different spreads.

In Monticchiello, we found a restaurant open all day until 8pm (perfect for our eating style) called ‘La Guardiola‘ which had gorgeous views, great service and yummy slow cooked homemade food. The portions were generous and everything felt very real and made with love.

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We also had a lovely Ribolatta soup and mashed potato & artichoke mousse at La Porta Osteria.  Ribolatta is ‘reboiled’ soup of vegetables but then bread is added to it the next day to thicken it and make it more hearty.

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