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Forget Chianti – these are the five hidden corners of Tuscany you must visit

The Val d'Orcia, seen from Pienza - Francesco Riccardo Iacomino
The Val d'Orcia, seen from Pienza - Francesco Riccardo Iacomino

Saturday morning in Gaiole in Chianti, a little town in the Tuscan heartland. A summer Saturday. A hint of cool in the air, but the promise of a beautiful day to come. Shopkeepers are raising their shutters and the Bar Centrale is doing a brisk trade in brioches and cappuccinos.  

Up and down the street, greetings are being exchanged. There’s Italian, of course, but also a lot of English. Dutch and German. But mainly English. Even those not talking give themselves away. By their deck shoes and shorts, you shall know them.

They’re here for a coffee, of course, but also to pick up yesterday’s Daily Telegraph, stock up on wine, buy cheese and prosciutto for lunch, maybe grab some fizzy water and a few Peronis for the fridge. All part of the many small things that make up the villa holiday experience, but also a vignette that confirms the cliché of “Chiantishire”, the idea that this tiny area of Italy is so busy with Brits it might as well be the Home Counties.

Top 10 | The most popular destinations for Britons
Top 10 | The most popular destinations for Britons

Clichés are clichés because they contain an element of truth. In summer there are a lot of Brits in and around Gaiole, and Greve, and Castellina, and the other well-known Chianti towns. Nothing wrong with that, of course. They’re here for good reason. Chianti has much of what is required – sun, landscape, villas with pools – for a summer of what the Italians call il dolce far niente – the sweet doing of nothing.

But they’re not here because Chianti is necessarily the best place for a Tuscan holiday. Chianti’s popularity is partly geographical – it lies between Florence and Siena, Tuscany’s key cities historically and culturally, so it’s accessible, for a start.

It was also the place early British expats in the know – we’re talking the early Sixties – first came across going-for-a-song farmhouses that Tuscans, having drifted from the land since the Second World War, no longer worked or wanted. So the region’s appeal was also partly accidental.

Look at Chianti objectively, however, and it’s attractive enough, but truth be told, the towns are low on culture and the scenery – often high, wooded hills – is not always the iconic Tuscan landscape (cypress, vine, olive) of popular imagination.

Chianti is a known name, a brand that sells; a region whose history of early expat colonisation means there’s a large stock of former farmhouses to rent. But it’s also tiny. Tuscany covers 8,875 square miles – about twice the size of Yorkshire ­– of which the Chianti Classico wine region, a useful marker for an area of ill-defined borders, covers just 100 sq miles.

That leaves a lot of Tuscany to go around. Below we’ve described some of the best alternatives to Chianti, all of which are easily its equal – and often its superior – in terms of art, food and landscape. 

And all places, for the most part, where the British still hesitate to tread.

Regions of Tuscany
Regions of Tuscany

The Val d’Orcia

Whereas Chianti is a few miles north of Siena, the Val d’Orcia – the Valley of the Orcia – is a few miles to the south, but where Chianti is high, wooded and enclosed, the Val d’Orcia is broad, open and bare, a landscape so iconic, with its classic, cypress-topped hills, that it has Unesco World Heritage status.

Nowhere this beautiful can be entirely unvisited, of course. The three key towns – Pienza, Montalcino and Montepulciano – are well known, and deservedly so.

Visit them, definitely, but early or late in the day. In Pienza, do your sightseeing (don’t miss the panorama behind the Duomo) and then book an outside table for lunch at Terrazza Val d’Orcia (terrazzavaldorcia.com) for one of the great Italian, never mind Tuscan views.

Pienza - Credit: GETTY
Pienza Credit: GETTY

Montepulciano is about Vino Nobile, its celebrated red wine (stradavinonobile.it), but it has plenty of sleepy corners, an art-filled cathedral and an excellent summer arts festival (fondazionecantiere.it); Montalcino, my favourite, is also about wine – the exceptional Brunello di Montalcino – but don’t miss the Museo Civico (museisenesi.org) nor the nearby Abbazia di Sant’ Antimo (antimo.it), one of Italy’s loveliest Romanesque buildings.

Away from this triumvirate, however, there are plenty of sleepier villages. Top of my list are Castiglione and Rocca d’Orcia, Murlo, Sant’Angelo in Colle, Radicofani, Castiglioncello del Trinoro and tiny Camigliano, with its exquisite main square (Piazza San Biagio).

Castiglione - Credit: GETTY
Castiglione Credit: GETTY

More to the point, the countryside in which you’ll find your villas is less populated in summer than Chianti. If you’re being especially choosy, the scenery in the west, around Montalcino, is lower and less verdant, while that in the east (bounded by Asciano, Sinalunga, San Quirico d’Orcia and Sarteano) is more pastoral and more obviously pretty.

The Maremma

The past casts a long shadow in Tuscany, but especially in its southwest corner, hard by the border with Lazio. Here the towns are few and the countryside empty, in part a legacy of the malarial marshes that discouraged settlement until as late as the Fifties.

The Maremma's pastoral, low-hilled countryside - Credit: getty
The Maremma's pastoral, low-hilled countryside Credit: getty

This is still largely unknown territory, though the coastal enclaves – Capalbio and Chiarone, with their long, empty beaches – have become quietly popular with more well-heeled Romans. But it is inland that you want to head, to the pastoral, low-hilled countryside flanking the Albegna and Fiora valleys.

On a villa holiday it’s always nice to have a pleasing main town close by, a place for ice cream, museums and market-day visits. Here, it must be said, you don’t get one: Grosseto, the regional capital, has a decent enough old centre, but it’s no beauty.

Montemerano - Credit: getty
Montemerano Credit: getty

What you do get, above the countryside, are lovely villages. Some, such as Montemerano, Magliano in Toscana and San Martino sul Fiora, are charming in the classic Tuscan manner – sleepy squares, geranium-hung streets – while others combine that same charm with plenty of genuine artistic, cultural and gastronomic interest. Among the latter, Sovana is a standout, thanks to two wonderful churches (Santa Maria and the Duomo) and a picture-perfect main street (Via di Mezzo). Sorano and Pitigliano are also captivating, partly for their striking, crag-top locations and partly for their surroundings, which are riddled with remarkable Etruscan tombs and ancient sunken roads (leviecave.it).

Pitigliano - Credit: getty
Pitigliano Credit: getty

I would also make special journeys to visit Roccalbegna – climb the hill above the village for some sweeping views; and to the Giardino dei Tarocchi, (giardinodeitarocchi.it), an extraordinary garden created around the sculptures of the French-American artist Niki de Saint Phalle. And if you want a day of walks and upland cool, drive to the shady, forested slopes of Monte Amiata to the north.

Giardino dei Tarocchi - Credit: getty
Giardino dei Tarocchi Credit: getty

The Pratomagno

Frances Mayes has a lot to answer for. Until the Nineties, Cortona, a once-sleepy hilltown close to the Umbrian border, had few visitors. Then Mayes published Under the Tuscan Sun and Bella Tuscany, based on her experiences in Cortona, and visitors flocked to the place where she had realised the expat dream.

Cortona, and the hills to the east, always had expats, but they were early adopters, artists and other refugees from the mainstream. After Mayes, though, any remaining rural homes were quickly snapped up, prices soared, and the pioneering expats tidied up their homes for summer rentals.

As a result, Cortona, on a summer Saturday, is as busy, if not busier, with foreigners, as Chianti. To escape, head north, either a short distance, to the Chio valley east of Castiglion Fiorentino, or to one of Tuscany’s last frontiers, the region southeast of Florence, the Pratomagno.

The Pratomagno is one of Tuscany’s last frontiers - Credit: GETTY
The Pratomagno is one of Tuscany’s last frontiers Credit: GETTY

Close to Florence, but high and wild, this is green, hilly country that’s as beautiful as any Tuscany; a wonderful enclave bounded by a wide arc of the Arno river, where wooded uplands rise to breezy, grassy-topped mountains more than 5,000ft high. True, there are few towns – Loro Ciuffenna is the key base – and little in the way of obvious culture, save for the great abbey at Vallombrosa and a series of charming Romanesque churches for those with the patience to hunt them down (at Stia, Romena, Sietina, Strada and elsewhere).

The great abbey at Vallombrosa - Credit: GETTY
The great abbey at Vallombrosa Credit: GETTY

But there is Arezzo, with its Piero della Francesco frescoes, and Florence, of course, which in summer, with its heat and crowds, is a place you really only want to see on a day trip, and preferably by train – an outing for which a villa in the Pratomagno makes the perfect base.

The Garfagnana

The Garfagnana region north of Pisa offers the best of both worlds: cultural allure combined with fine countryside. The region is centred on the Serchio valley and is flanked by two majestic but contrasting mountain ranges: to the west are the Alpi Apuane (parcapuane.it), high (over 6,000ft) and jagged peaked (hence “alps”), and to the east the Orecchiella (parcoappennino.it), just as high, but rounded, gentler to look at and swathed in forests of beech and chestnut. In the Serchio’s southern reaches, near Lucca, you’ll also find scenery in the classic Tuscan mould – cypresses, low hills, vineyards, olive groves – a region the villa companies usually describe as the Colline Lucchesi, or Luccan Hills. 

The Alpi Apuane - Credit: getty
The Alpi Apuane Credit: getty

But elsewhere, away from the valley floor, these are some of Tuscany’s wildest landscapes, with the advantage over lower Tuscan enclaves of more bearable summer temperatures.

These same landscapes, however, make getting around slower. Once you’re in your villa, it can be a long drive (or train ride) to Lucca, the area’s main cultural focus and one of central Italy’s most laid-back and captivating towns. Castelnuovo di Garfagnana is the region’s key town, and it’s fine as far as it goes – for supplies and a coffee in the square – but Barga to the south has far more charm and interest.

This is a little town that’s largely still under the radar, but it has a nice setting, with views to the mountains; a sprinkling of good restaurants (tiny Da Aristo in Piazza Salvo Salvi is a favourite); a wonderful, art-filled cathedral; and a rich cultural life that finds summer expression in Barga Jazz (barganews.com), Opera Barga (operabarga.it) and other festivals.

The beautiful Italian island you've probably never heard of
The beautiful Italian island you've probably never heard of

Vinci and the Val di Pesa

These are areas with no recognised name, so let’s do what the local winegrowers do, and call one the Colline di Vinci – the Vinci Hills. Leonardo da Vinci was so called because he came from Vinci (www.vinciturismo.it), a small town 15 miles (24km) west of Florence.

To this enclave, with Pistoia to the north and Empoli to the south, let’s add the hills between Empoli and Poggibonsi, bounded to the east and west by the Pesa and Elsa valleys.

Pistoia - Credit: getty
Pistoia Credit: getty

Follow this line of hills southeast and you come immediately to Chianti, and Chianti, more or less, is what you get in both these areas – the same landscapes (woods, vineyards), the same winding country roads, the same small towns... but not the same number of people and, on the whole, not the same elevated rental prices. Properties with the charm of Chianti’s traditional villas are harder to find, but they are there.

As in Chianti, you have the option of day trips to Siena and Florence – given the problems with parking and taking a car into Florence, take a train from Empoli or San Casciano. You are also well placed for visits to Colle di Val’Elsa (www.terresiena.it) – which has a delightful medieval upper town (Colle Alto) – and San Gimignano (sangimignano.com), famous for its medieval towers, but hugely popular, so visit early or late in the day in high season. 

Can't afford Tuscany? | Try the English alternative
Can't afford Tuscany? | Try the English alternative