Explore Tuscany’s Most Beautiful Hill Towns

One of the most popular small group tours of Italy among nature lovers and history aficionados consists of an itinerary of Tuscany’s loveliest hill towns. These sun-soaked villages in northern Italy represent most people’s idea of a quintessential Italian holiday: traditional wineries offering incredible wine tasting opportunities; late-medieval farmhouses that have been beautifully preserved through the centuries; mouth-watering homemade pasta dishes made with stunning local produce; and endearing old-timers soaking up the sun in the village’s main square.

There are plenty of these beautiful towns speckled throughout Tuscany, and you won’t go wrong wherever you go. However, after years of helping people make the most of their small group tours of Italy, I have come up with my must-see hill towns of the region.

Cortona (Province of Arezzo)

This small village in the Chiana Valley exudes medieval character, with narrow, steep, stone-paved streets and surrounded by a stone city wall, bits of which date back to 7th century, when the original Etruscan wall was built. Despite its small size, Cortona offers plenty of highlights to visit during your stay – from the Piazza della Republica where the locals congregate and you can find delicious Italian coffee, to the Basilica di Santa Margherita, a neo-gothic style church originally built in the 11th century, and to Le Celle, built in 1211 by Saint Francis of Assisi.

Once you’ve admired all these stunning pieces of history, you can stroll back to the centre of town to sit down in the shade and cool down with some delicious artisan ice cream.

Montalcino (Province of Siena)

If you’re looking forward to tasting some magnificent wines, Montalcino should firmly be part of your itinerary. With stunning, dreamy panoramas of the countryside, this enchanting little town is famous all around the world for its production of Brunello, one of the best Italian red wines. You can enjoy it in any of its great restaurants and wine bars, such as La Crocina, where homely service is perfectly combined with innovative dishes like wild boar pinci.

Moreover, if you are travelling in July, you can even take advantage of the Jazz & Wine Festival, where you can combine two fantastic pastimes.

Montepulciano (Province of Siena)

If you are keen to continue with the wine-themed excursions, this lovely town is a mixture of medieval and Renaissance features and is home to Vino Nobile di Montepulciano – a wine understood to be, among connoisseurs, one of Italy’s finest. Just off the town’s main square you can see the Contucci Cantine, the old town jail that has been converted into a wine cellar that extends all the way underneath the square itself. A great highlight of our small group tours of Italy, this cellar offers walking tours and wine tastings with experts.

San Gimignano (Province of Siena)

A UNESCO World Heritage Site, San Gimignano should be on any culture-oriented traveller’s list. With stunning examples of Romanesque and Gothic architecture, wonderfully-preserved, unique tower houses, and some excellent frescos dating back to the 14th and 15th centuries, you won’t be short of interesting places to visit. Moreover, the town is renowned for its production of saffron, olive oil, and white wine – all of which are great souvenirs for foodies to take back home.

Volterra (Province of Pisa)

Slightly more off-the-beaten-path than the previous towns, Volterra is worth a visit for its Etruscan Museum, which holds fascinating artifacts from centuries BC, its city hall, which claims to be the oldest in Tuscany (dating back to the 13th century), and, most interesting of all, its Fortezza Medicea, a prison that houses a restaurant renowned in the region for being a rehabilitation scheme for inmates where you’ll be served great, traditional food. It even has to be booked weeks in advance due to its popularity!

These villages are only a handful of the beautiful places scattered around the region of Tuscany, so if you are interested in discovering them more in depth then our small group tours of Italy’s Tuscan region will take you to them.

Antonio Nobile is Tour Operator & Researcher at Caspin Journeys, a specialist provider of small group tours of Italy, England and Spain. Following in the footsteps of the company founders Pino and Caroline, he has exceptional insider knowledge and a personal devotion to all the tours he organises.

Writer and Online Marketing Manager in London.