Roccastrada, Tuscany

Tuscany’s Prettiest Medieval Villages

When I think of Tuscany, I imagine a vineyard-lined landscape with rolling hills and pretty little villages dotted about the place. That’s exactly what we were greeted with when we arrived there for our Italian getaway.

Whilst Tuscany is home to some of Italy’s most famous cities such as Florence, Pisa and Siena, we were keen to live like locals and discover some of its smaller hidden gems. As hiring a car is the only way to truly experience Tuscany, we headed out with our trusted sat-nav to uncover some of the region’s prettiest medieval villages. Here are our favourites…


Roccastrada is a hill-top medieval town in the heart of Tuscany. We stayed here for the majority of our trip in a charming Airbnb apartment, which was nestled amongst rustic buildings and narrow cobbled streets. It was the perfect Tuscan home from home, and just a stone’s throw away we could enjoy the fantastic panoramic views of the towns and villages below.

Roccastrada, TuscanyRoccastrada, Tuscany

We felt very much like one of the locals in Roccastrada with its authentic, non-touristy atmosphere. In the mornings you could hear the hustle and bustle of the Piaggio vans to-ing and fro-ing, and in the evenings you could see local families heading out for some freshly baked pizza.

Roccastrada, TuscanyRoccastrada, Tuscany


Montemassi is a hill-top medieval village with an impressive ruined castle that you can spot from a mile-off. We approached Montemassi in the late afternoon and ran like little schoolkids up the steep and uneven steps to catch the sunset from the top. The views of the Tuscan landscape were simply spectacular. Other than a few pigeons in amongst the ruins, we were the only ones up there and it felt eerily quiet and unspoilt.

Montemassi, TuscanyMontemassi, Tuscany

Back down the steps to the main village area, we enjoyed a delicious dinner at a restaurant called Il Guidoriccio. For meat lovers I’d highly recommend the antipasti platter – a range of cured meats accompanied by some super soft bread drizzled in copious amounts of olive oil and balsamic vinegar. The pizzas too were fantastic!

Montemassi, TuscanyMontemassi, Tuscany


Pienza was probably the most picturesque of all the medieval villages we came across. The long and winding journey in takes you through fields upon fields of countryside, with olive groves and vineyards are far as the eye can see. Whilst a little more touristy than the other two villages, it was bursting with history and culture and had a really laid-back feel. Once again, the views were breath-taking!

Pienza, TuscanyPienza, Tuscany

Pienza is lovely place to stroll around and wander through the little lanes and alleyways. Keep an eye out for the romantically named Via dell’Amore or “Lover’s Lane”. We grabbed a gelato and headed for one of the many cafes/bars overlooking the countryside. A perfect place for an afternoon spritz with a view! And of course, you can’t visit Pienza without trying some of its famous local produce – pecorino cheese (made from sheep’s milk).

Pienza, TuscanyPienza, Tuscany

Here’s a short video of our trip to Italy:

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