Seeking out the best towns to visit in Tuscany can be harder than you might think as many of them are over-touristed and have lost their original charm. But if you ask where the Italians go, that’s easier. It is the Maremma region and places like Pitigliano in Italy. The Maremma is known for its great wine, sleepy hillside towns and thermal springs which have been enjoyed by Italians for thousands of years. It is also home to beautiful Pitigliano. I have a very fond attachment to Pitigliano after stumbling into the town by accident years ago. After spending time travelling throughout Europe the need for a well-earned break was calling and Pitigliano came to the rescue.

This magic hillside town built on volcanic rock is a piece of Tuscany that still has the feel of a town not yet discovered by the tourist hordes. Pitigliano is a town worth exploring for a few days and not just dropping into for a fleeting visit. Ideally Pitigliano is a place best taken in slowly with its labyrinth of cobblestone lanes and hidden nooks and crannies that reward visitors with stunning views of valleys and neighbouring hills. Perhaps the biggest delight is the locals who are genuinely friendly to everyone that passes through. This was especially true when our family stayed for three days in a beautiful Airbnb. At the end of our stay, it felt like we were saying goodbye to old friends.

Pitigliano dates back thousands of years, from the early Etruscan communities of the 4th century to the Romans and on to the fortresses of the Middle Ages. Exploring this part of Tuscany is fascinating for the wine alone but if you want to dive into a little history, Pitigliano has it in spades. Start with exploring the Etruscan tombs at the base of the hill that holds Pitigliano and work your way up through the centuries by foot through a charming trail that winds up to the town. Just be sure to have a guide or a map as it’s easy to wander down the wrong trail and get a little lost.

Exploring the town is the biggest drawcard with its labyrinth of winding streets and alleys that can lead you to many amazing shops, restaurants and hidden bars. There is also a fortress and churches that are worth exploring plus there is the history of the Jewish community who the town has protected since the 1400s. This is why the town also has the nickname ‘Little Jerusalem’. Food in Pitigliano includes an abundance of incredible local flavours like wild boar, mushrooms and many locally produced cheeses.

Two standout restaurants are Ristorante Il Tufo Allegro and Trattoria La Chiave del Paradiso, both of which specialise in local produce and are worthy of a long lunch or dinner. If you’re on more of a budget opting for a picnic is also a great idea as the town specialises in cured meats and has a couple of great bakeries filled with tempting delights. There are also plenty of stunning spots to sit and enjoy your picnic throughout the town. Be warned there are also a lot of stairs which are great going down but not as much fun coming back up.

Wine is also a big deal here with family wine cellars that date back many generations. We found this out first hand when our son stumbled upon two locals making wine in their cellar. We were invited inside and given a lesson in wine and history with the bonus of making some new friends and tasting some amazing local wine. This type of experience is one of the great joys of travel and part of slowing down and enjoying the moment.

Art is another drawcard with many local artisans producing innovative and one-off pieces. These art studios and shops produce everything from paintings to pottery, fashion and leather work. My favourite thing to do in Pitigliano is wandering the streets and exploring these shops and finding unique one-off treasures to bring home. Don’t miss Altaluna which produces original artworks ranging from candle holders to sculptures. This town will have you melting your credit card in minutes as there are so many tempting and unusual stores.

Visiting Pitigliano is also special because you can stay in the heart of an ancient town side-by-side with locals. Accommodation ranges from a few simple hotels to a handful of apartments and Airbnbs. Do some research or ask at the tourist information office when you arrive. On our first visit to Pitigliano we decided to stay last minute and asked a local who soon had our family sorted with a cousin who rented us a renovated apartment in the heart of the old town. My second stay here had us admiring the town from a high terrace enjoying a glass of wine with an assortment of local cheeses. The catch was we had to do it wrapped in blankets as the weather turned unseasonably cold.

Disclosure: The writer paid her own way to visit Pitigliano and would do so again without hesitation.

If you are heading passing through Rome on your way to Tuscany and looking for things to do, we enjoyed seeing the Colosseum, touring in a vintage Fiat 500 and checking out these Rome hidden secrets.