The perfect Tuscany road trip – part 1 15

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Our Tuscany Dream Road Trip – Part 1

A lot of people think Tuscany is overrated and search out lesser known parts of Italy to explore. But, although each region has many wonderful things to offer, there’s a reason Tuscany is up there on every Italy lover’s list. Many consider its cuisine the best in the country. Drive through Val d’Orcia and you’ll see scenery that will leave you speechless and of course there are the people, ready to teach you anything and everything about their region if you show the slightest interest.

We love Italy, but no matter where we travel in the boot, we always save a bit of time for our first love: Toscana. We’ve been to many hill towns – always from a home base – and have often dreamed of returning to these places on an epic road trip. For us, this would be the perfect Tuscan road trip.

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In the South East of the region, Pitigliano is known as Little Jerusalem because of the historical presence of a Jewish community. Although there are hardly any Jewish people left in the town, the synagogue is still officiated at times.

Below the town, you can walk the Vie Cave, the old Etruscan paths. There is also an archaeological park and several museums to visit.

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One of the cities portrayed in the movie Twilight, it is known world wide for its wine, Vino Nobile. Some say it’s Italy’s best and our favorite place to get it is Cantina Contucci. Contucci is the only producer that still produces wine in the family castle, right in town. They offer a free wine cellar tour and tasting.

For coffee and something to eat, stop in at Caffè Poliziano, established in 1868. It is one of the prettiest café/bars in town.

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The farm co-op in Volterra


Another Twilight movie city, it has many points of interest such as the Volterra Cathedral, which was enlarged after the 13th century earthquake and original Etruscan walls (3rd and 2nd centuries BC).

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raw milk dispenser outside the farm co-op, Volterra

We discovered a farmer’s cooperative that showcased products from neighbouring farms and included a raw milk dispenser on the outside. Insert 1€ and fill up a 1L bottle with ice cold raw milk.

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Piazza del Campo in Siena


Known for the Palio (horse race) that happens two times a year in Piazza del Campo, Siena also has one of the most impressive Duomo in Tuscany. If you visit the Duomo, make sure to check out the library through a small door on the left side. Siena also hosts a large Christmas market that counts as many food stands as handicraft stalls.

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The pool at Casamonti Estate, Castellina in Chianti

Castellina in Chianti

Castellina is a small town of approximately 2800 inhabitants about half an hour drive from Siena. In the summer it’s bustling with tourists, but come winter it’s so quiet you can hear a pin drop.
About a 10 minute drive away is Casamonti Estate, an agriturismo where they grow olives and grapes and raise the famous white belted pig, the Cinta Senese.

You can make an appointment for a tour and tasting of the products they create here by emailing

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Palazzo Vecchio, Florence


The capital of Tuscany, Florence is one of our favourite Italian cities. They serve the local specialty, lampredotto sandwich, made with the cow’s 4th stomach, seasoned and boiled. The thinly sliced stomach is piled on a crusty bun that is drenched in cooking liquid. You’ll find it at the market and street side stands. If you want a different kind of sandwich, try i Fratellini or Alimentari Uffizi for some of the best in town.

The Palazzo Vecchio is a must when visiting. It’s open late (midnight) most days, so go late to avoid the crowds.

The Basilica della Santissima Annunziata is a church that looks like nothing special from the outside, but inside we would venture to say that it is decorated with more gold than most Italian churches and that says a lot.


Stay tuned for Part 2, which will start in the beach town of Viareggio and take us all the way to the mountain village of Colonnata!

Where would you go on your Tuscan dream road trip? 


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About Nat and Tim Harris

Together for close to a quarter of a century, A Cook Not Mad‘s Tim and Nat have indulged their passion for life and experience to the fullest, but they feel most alive when traveling, cooking and eating. An award winning chef, Tim has dedicated his life and career to cooking and the pursuit of honest food. As a professional photographer, Nat records their adventures with incredible pictures of everyday life and the extraordinary. They believe that everyone should get to know a culture by learning about the foods they eat and living like locals as much as they can.

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