Three off-the-beaten-track Tuscan towns that deliver charm and local tradition without the crowds

When you grow up, as I did, in the middle of a Venn diagram that intersects Italian heritage, love of history, art history and food, you see each Tuscan hill town as an entirely distinctive thing. This one might have an unusual tower on its town hall. That one might have a particularly lovely Madonna in its church. And on...

Here's the truth: unless you’re obsessed with Tuscan hill towns, they’re pretty much all the same.

There will be walls punctuated by guard towers, probably making a picturesque ensemble visible for miles. You’ll enter through a big gate, probably long bereft of its portcullis or any defensive gear. All roads will lead to a main square on which you’ll find a big, blocky town hall with a high tower sticking out of it. There will be at least one main church, probably on the same square as the town hall, and it is likely to have a bell tower. Main streets will be lined with imposing houses: square, blocky stolid buildings with no windows on the ground floor and no opening other than a big, arched gate that, if opened, will give you a glimpse into a generous courtyard around which the house is built. There will be a handful of other little squares, maybe some other small churches and several picturesque viewpoints from which you can take  in the spread of countryside below. Tourist shops will sell ceramics, leather and fine linens. There will be a lot of small, crowded food shops hawking jars of truffle-based products, dried porcini, specialty pastas, sausages and local wines. 

If you go to several and don’t make notes, you may find it challenging to differentiate your photos.

Why is it, then, that everyone follows the same paths to Sienna, San Gimignano and Lucca? (The last isn’t on a hill but the comparison still applies.) Tuscany is full of places that art historians might dismiss as Tier 2, but most visitors will find memorable. Here are three.

Colle di Val d'Elsa

Not far off the main road from Florence to Siena (SR2), here's the perfect example of a little gem people pass by on their way to more famous sites. Free parking suggested I was off the tourist track; not hearing a word of anything other than Italian in the excellent pastry shop where I had my breakfast confirmed it. 

In the valley of the river Elsa is a sprawling, modern industrial town that makes the bulk of Italy's glassware. The original walled town above it, however, is a picturesque gem almost free of free of crowds.  A single road starts from an impressive Renaissance gate, slopes down through venerable buildings to a branch where you can continue downward into the new town or head left for the old one. Cross a bridge that links two hills, go through another gate that’s also a Renaissance palace, and you’re into the original walled town. Again, it’s just a single road, probably no more than 400 metres from one end to the other. In the centre is a large square with the requisite town hall and duomo. More interesting, a little further on, is the tiny Santa Maria in Canonica, built in the 1100s and imbued with a sense of deep peace and antiquity. Medieval wall paintings survive and there’s an almost Byzantine Madonna and Child illuminating the gloom as sun from the one small window shimmers off its gold leaf.

While most of the buildings here are early Renaissance, the whole place has a feel of enormormous age, more profound than Siena or Florence. It may be because those main towns have been so well preserved while Colle has the feel of everyday life about it. Many of the walls are a makeshift mix of brick and stone, with no fancy facing to disguise it. Many reveal centuries of renovations and re-working; you can see multiple arches, doorways and windows filled in and moved around in building facades. Throughout the upper town there are views down picturesque side alleys, many with views over the gorgeous countryside beyond.

There is a small glass museum not far from the church, and a handful of tourist shops. Despite the fact that

the place is known for glass, the three windows I peered in were potters, all producing modern stuff along side traditional patterns. There are a few restaurants, and in the upper town the exceptional Pastry Mario Barone. I suspect locals come from a broad area to patronise this lavish shop, its air conditioning, sleek white interior, chandeliers and pop music at odds with the sleepy town outside. I’ve rarely seen a more impressive array of baked goods in Italy and a fridge full of personalised birthday cakes being picked up by locals was constant. Come here for breakfast, then have a stroll around town.

There is nothing in Colle that would make any guidebook’s Top 10 list. Its greatest claim to fame is as the birthplace of Arnolfo di Cambio, who promptly left to design great things in other cities, like the Duomo in Florence. (There’s a statue of him in front of the family home in a pretty little square next to Santa Maria in Canonica.)  Yet in atmosphere and antiquity Colle has everything you could want from a Tuscan hill town. Minus the tourists. If it hadn’t been so brutally hot, I could have easily spent the day here with a sketchbook, trying to capture one fabulously picturesque scene after another.

Volterra

Volterra, on the other hand, can present a long list of reasons why it's a "must see". Its location 25 miles west of the Florence-Siena flight path, however, and the fact that it's relatively challenging to get to on public transportation, means it's still comfortably off the beaten track. I had worried that its appearance in the blockbuster Twilight franchise as the HQ of European vampires might have turned it into another Dubrovnik/King's Landing. Thankfully, other than one tattered movie poster and three goths heading into a bar at dinner time, Volterra was still a magical place with more layers of history than your average Tuscan town, and fewer tourists appreciating them.

The town, pictured at the top, immediately differentiates itself with its landscape. You’re approaching the sea and the Maremma salt marshes here. The valleys between the hills are broader, more likely to be gold with grasslands and wheat than green with oak, olive and vines. There are fewer towns. It all feels wilder and more mysterious, and Volterra itself seems to sit higher than other towns in splendid isolation. Its roots are more ancient than most towns in Italy, a flourishing and sophisticated Etruscan capital from the 9th to the 7th century BC when Rome was only just establishing itself as a village of mud huts. The Etruscans remain one of Western Civilisation’s most intriguing peoples, clearly sophisticated and literate (one of the best collections of their art is here at the Guarnacci Museum, and you can scramble over their acropolis at the town’s highest point) yet almost no written records exist. One theory is that the Romans, fiercely jealous, destroyed all the Etruscan literature so that all greatness in Italy would originate from Rome. Any look around the treasures taken from Etruscan tombs, however, makes it clear these were people as sophisticated as the ancient Egyptians or the Minoans. I suspect the strange landscape and immense antiquity combined to inspire Stephanie Meyers to establish her vampires here; it feels entirely credible.

The Romans might have taken Volterra’s written past away, but they left a magnificent theatre and bath

complex which comprises probably the best Roman ruins in Tuscany. Cut into a westward-facing hillside, it’s marvellously picturesque to look at from above and on a clear day you can see all the way to the sea from here. Next come the medieval and Renaissance layers, here looking much more like other towns with a town hall that has doubled for Florence’s Palazzo Signoria in historical dramas, and numerous aristocratic Palaces. There are some unusually broad and gracious shopping streets to balance the quintessential winding lanes, and a particularly splendid Medici fortress set in a verdant park that’s no doubt so imposing because it still functions as a prison.

Volterra is also differentiated by its alabaster. The town sits on top of the finest seam in Italy, and has been producing precious things from the stone for its whole history. The usual Tuscan tourist shops sit beside alabaster workshops and boutiques full of everything from affordable bits of jewellery and small decorative objects to fabulously expensive sculptures and light fixtures. 

While there are plenty of tourists here, it doesn’t get the jostling crowds of Florence and you’ll hear much more Italian being spoken. The restaurants feel particularly authentic. Check out Brasseria del Grifone, a fantastic micro brewery where the brewmaster is on site to talk you through his range of beer styles and his mother is in the kitchen knocking up snacks; Isola del Gusto, a tiny gelato shop showing off a range of international awards and a visit from American travel guru Rick Steves … and yes, it was the best gelato I had this visit to Italy; or dinner at Torre del Porcellino, wizards at creating variety from pig and wild boar. I wish we’d been closer so we could have eaten there more than once. My wild boar in a chocolate and orange sauce was the most sophisticated cooking I had this trip, and everyone else was rolling their eyes in ecstasy at their choices. 

Monteriggione

Anyone who’s driven between Florence and Siena would have seen this magnificent circle of medieval walls on its hilltop directly next to the highway, but I’d never met anyone who’d visited. I’d driven by it multiple times over the years, always in too much of a hurry to get to somewhere more important. You could certainly argue that it’s at its best observed as a whole from a neighbouring hillside; there’s not that much inside the walls. But it’s definitely worth a stop, especially if you’re trying to go beyond the usual itinerary. 

Siena built this place in the early 1200s as a front line fortress in its wars against Florence. Though it saw more than 200 years of violence before the Florentines finally won, the perfect circuit of walls still remains, punctuated by the crumbling ruins of 11 towers. Inside there are about 25 buildings surrounded by walled gardens, and a tiny permanent population. Unsurprisingly, the buildings are heavily restaurants, shops and B&Bs. You park below and hike up a landscaped path to go in the main gate. It’s also no surprise that the town was used as the setting for the Assassin’s Creed games set it Renaissance Italy; the whole place looks like a film set.

We turned up for Monteriggione’s annual medieval festival, obviously the biggest event of the year for the tiny population of locals. Coming at it hard on the heels of the Chalk Valley History Festival, I confess to being more than a bit disappointed. English re-enactors obsess over authenticity and go to impressive lengths with costume and accessories. The Monterrigione gang was sporting a lot of visible zippers, nylon capes, womens’ support hose instead of tights and obviously modern shoes and boots. There were a few historical re-enactments by people with slightly better costumes, but overall it was a bit more like a medieval-themed costume party and excuse to eat and drink. 

Activities didn’t start until 4 pm, the best bands were rocking at 10 pm and fireworks wouldn’t close things down until 12:30 am. Facebook photos from after we left showed a packed festival crowd after dark, dancing into the wee hours. It was fun to wander through in the late afternoon, but we were happy to leave it behind and head to a local restaurant for a quieter dinner. Outside of festival time, I think Monteriggione would be a great place to stay for a night or two, or to wander in the late afternoon before a dinner at one of its local restaurants. 

La Dama nella Vigna, where we went instead, is a modern, purpose-built restaurant nestled in the vineyards below the walled town. Even on busy nights the place looks empty, because the kitchen and bar are at the front and the whole place faces onto the vines at the back. In summer, many of the tables are nestled into the vines themselves. Contrary to expectations, this isn’t a restaurant related to the vineyard itself or the wines that come out of it; the wine list pulls together bottles from across Tuscany. The food is resolutely Tuscan and all about the meat, flamed over coals on a massive grill. While we all opted for the classic pici with wild boar ragu, this is clearly the kind of place to go for a massive bistecca fiorentina. 

Like everything else in this post, La Dama was full of as many Italians as visitors, and worth another visit. Tuscany’s hot spots may be amongst the most crowded tourist locations in Europe, but with a bit of effort  it’s actually possible to find more authentic and enjoyable substitutes.