Italy's Prettiest Villages

San Gimignano, Tuscany

Could Italy be the prettiest country in the world? Possibly. Italy has a whopping 53 UNESCO World Heritage sites, the highest number for any nation-state. The sites range from Roman Ruins to Norman Castles, Medieval caves to stunning coastal towns, such as Cinque Terre in Liguria. We have scoured the length and breadth of the country to compile a list of what we think are some of Italy’s prettiest villages. If you are planning an Italian getaway this summer, do it in style and visit one of these stunning villages. Let’s just hope they serve Peroni Nastro Azzurro!


Located in Apulia, a lesser-known region of Italy that sits next to Puglia, Alberobello is famous for its unique trullo buildings. Dating back to the 15th century when this region was ruled by the Kingdom of Naples, the trulli of Alberobello have been designated as a UNESCO World Heritage site since 1996. If you want to see the trulli in all their glory, Alberobello is the place to go.

Alberobello, Apulia


This sleepy, charming village nestled in the hills of the Messina province offers a real and authentic taste of Italy. Made famous in the 1970s when Francis Ford Coppola filmed scenes from The Godfather in the village, a trip today gives you a chance to visit the famous Bar Vitelli located on the edge of the main square of the village. A short walk up the hill from the town square, the Capuchin monastery (Convento dei Cappuccini) offers stunning views of the surrounding countryside and inside, a functioning crypt awaits those willing to enter.


The pearl of Lake Como, Bellagio is famous for its beautiful villas overlooking the lake. The narrow cobbled streets are perfect for exploring on foot and stopping by the local artisan shops that showcase the finest Italian wares. With the Alps in the background overlooking the lake, one of the restaurants on the water’s edge is the perfect setting to soak up the view.

Bellagio, Lombardy

San Gimignano

A walled medieval town nestled on the hillside about halfway between Florence and Siena, its stand out feature is the 72 tower houses built by Patrician families as symbols of their wealth and power. On the UNESCO list since 1990, nowadays a visit to San Gimignano offers a chance to enjoy the local white wine, the Vernaccia di San Gimignano and homemade pasta in a saffron sauce.


Another UNESCO World Heritage site, Matera is known as “Città dei Sassi”, the city of stones. It’s one of the most ancient towns in Italy, if not the world. Located in southern Italy in the region of Basilicata, the village is renowned for the sassi, ancient caves that are carved into the rock of the hills. It’s a place like nowhere else!

Matera, Basilicata


Next up is one of Umbria’s medieval hilltop towns Montefalco, known as the ‘balcony of Umbria’ because of its views over the plains, the main preoccupation of the village is producing fantastic wine. Overshadowed by its bigger brother Assisi, the village of Montefalco offers the real experience of Italy, away from the coach parties and reheated pizza.

Montefalco, Umbria


We don’t use the word epic lightly, but in the case of Positano, it is justified. The jewel in the crown of the Amalfi Coast, Positano seems to tumble down from the cliffs to the sea, creating steep and narrow streets that are crammed with shops and restaurants. It makes a great base for exploring the local islands of Capri and Ischia by boat.

Positano, Campania