[post_thumbnail size="header-narrow"]

Three Historic Hill Towns of Tuscany

Close your eyes and conjure an iconic view of Tuscany… I’m fairly certain the vision of rolling sunburnt hills and crumbling fortress towns perched atop them will come to mind. For me, these towns are the pure definition of this much-loved region in northern Italy and, within their fortified walls, the cobbled streets and ancient architecture hold the secrets of a heritage so important, it changed the entire world.

Tuscany, Volterra town skyline, church and trees on sunset. Maremma, Italy, Europe

Culture Within a Culture

While on the surface these hill towns may appear similar, each has a culture distinctly its own. It is my enduring pleasure to be able to share this diversity with my clients in all its joyous Italian glory, through the vineyards, late medieval architecture and mouth-watering Tuscan cuisine.

Do I have my favourites? Well, I wouldn’t like to say, but here are three that certainly have a pretty special place in il mio cuore Italiano

Volterra: Pisa Province

Long before Twilight came to town, the Etruscans marched in and made their mark on the Tuscan landscape in Volterra. While it’s gained popularity in recent years as a setting in the famous Hollywood movie franchise, it’s still a little lower profile than some of the other hill towns – but no less important or beautiful.


For amateur historians, the fascinating Etruscan Museum houses a collection dating back to the 13th century. Simply wandering around the town (on a quiet day) amongst the magnificently preserved buildings makes you feel like it’s quite possible nothing has changed since then. For classical music lovers, Volterra is also very close to Andrea Bocelli’s hometown of Lajatico and his famous open-air Teatro del Silenzio.

San Gimignano: Siena Province

The glamour girl of Tuscany’s hill towns, San Gimignano is fondly known as the Manhattan of the Middle Ages, due to its unique skyline of torre (towers) that rise out of the historic city centre. It’s been named a UNESCO World Heritage Site for its amazingly well preserved Gothic and Romanesque architecture, and although it can get fairly hectic in high season, so can the real Manhattan, right? It’s really worthwhile braving the crowds, though, because San Gimignano is absolutely groaning with history, art and that wonderful Tuscan ambience. Don’t miss the magnificent 14th and 15th century frescos within the beautiful Santa Maria Assunta collegiate.

Beautiful view of the medieval town of San Gimignano, Tuscany, Italy

Montepulciano: Siena Province

Love wine? Of course you do, it’s why you came to Tuscany! Well, that and the food, of course, and Montepulciano is the ideal place to take a food and wine themed tour. This is one of the most popular of the Tuscan hill towns for that very reason (it produces the famous Vino Nobile di Montalcino wine), but it’s also home to some stunning examples of Renaissance and medieval art and architecture.

One of the highlights actually combines all its most appealing features in one: the ancient Contucci Cantine (a former jail) is now a massive interconnected wine cellar beneath the town square. I like to take my clients down here for tastings and they always leave just a little happier than when they came in…



These are just three of Tuscany’s stunning hill towns we include on our small group tours and I’d love the chance to share them (and the others) with you.