Tuscany Travel Guide

Tailor-made Travel

The typical tourist view of Tuscany as an idyll of olive groves, vineyards, hill-towns and frescoed churches may be one-dimensional, but Tuscany is indeed the essence of Italy. Aside from being the birthplace of the Renaissance era, and the Italian language evolving from the Tuscan dialect, to travel Tuscany is a sure-fire way to get a taste of authentic Italy.

Nowadays, Tuscany is one of Italy’s wealthiest regions, partly due to agriculture and tourism, but mostly because of the industrial centre. That said, Tuscany is predominantly rural, with the vast landscapes looking much like they did half a millennium ago.

The postcard images of medieval hill-towns set into the peaks, and rolling terraces of vines and cypress trees in the valleys below, is very much what you can expect to see on a visit to Tuscany today.

Read on below to find out more about planning your trip to one of Italy’s most famous regions, in our complete Tuscany travel guide. In addition, check out our round-up of the best things to do in Tuscany.

Where to go in Tuscany

Gorgeous hill-towns, idyllic countryside and some of the world’s finest collections of Renaissance and medieval art, Tuscany travel offers its visitors no end of riches. From the great cities of Florence and Siena, to the vineyards of Montalcino, here is a breakdown of the best places to go in Tuscany.


Florence was the most active centre of the Renaissance, flourishing principally through the all-powerful patronage of the Medici dynasty. Every eminent artistic figure from Giotto onwards – Masaccio, Brunelleschi, Alberti, Donatello, Botticelli, Leonardo da Vinci, Michelangelo – is represented here, in an unrivalled gathering of churches, galleries and museums.

The problem is, of course, that the whole world knows about the attractions of Florence, with the result that the city can be off-puttingly busy in high season. Visit our Florence travel guide to plan your trip and choose the best time to go.

Pisa and the central coast

The cities of Pisa and Lucca have their own fair share of attractions and provide convenient entry points to the region, either by air (via Pisa’s airport) or along the coastal rail route from Genoa. Meanwhile, Arezzo serves as a fine introduction to Tuscany if you’re approaching from the south (Rome).


Nearby Florence, Siena tends to provoke a less ambivalent response. One of the great medieval cities of Europe, it remains almost perfectly preserved, and holds superb works of art in its religious and secular buildings. In addition, its beautiful Campo – the central, scallop-shaped market square – is the scene of the Palio, when bareback horseriders career around the cobbles amid an extravagant display of pageantry.

The Sienese hill-towns

Tucked away to the west and south of Siena, dozens of small hill-towns epitomize the region for many visitors. San Gimignano, the most famous, is worth visiting as much for its spectacular array of frescoes as for its bristle of medieval tower-houses, even if it has become a little too popular for its own good.

The best candidates for a Tuscan hill-town escape are places such as Volterra, Massa Marittima or Pitigliano, where tourism has yet to undermine local character.

You may find lesser-known sights even more memorable – remote monasteries like Monte Oliveto Maggiore and San Galgano, or the sulphur spa of Bagno Vignoni.

San Gimignano

San Gimignano, 27km northwest of Siena, is perhaps the most visited small village in Italy. Its stunning hilltop skyline of towers, built in aristocratic rivalry by the feuding nobles of the twelfth and thirteenth centuries, evokes the appearance of medieval Tuscany more than any other sight.

And the town is all that it’s cracked up to be: quietly monumental, beautifully preserved, enticingly rural, and with a fine array of religious and secular frescoes. It takes around twenty minutes to walk from one end of town to the other, but it deserves at least a day, both for its frescoes and for its lovely surrounding countryside.

From Easter until October, San Gimignano has very little life of its own, with hordes of day-trippers traipsing up and down its narrow streets and filing in and out of its innumerable olive oil, wine and souvenir shops. If you want to reach beyond its facade of quaintness, try to come well out of season; if you can’t, then aim to spend the night here – the town takes on a very different pace and atmosphere in the evenings.


The dramatic location of Volterra – built on a high plateau enclosed by volcanic hills midway between Siena and the sea – prompted D.H. Lawrence to write that “it gets all the wind and sees all the world – a sort of inland island”. Indeed, you can often find seashells embedded in the paving of streets and squares. Volterra is one of the most ancient of all Etruscan communities, and still abounds in Etruscan artefacts.

Busy but still atmospheric, the town’s walled medieval core is made from the yellow-grey stone panchino. Tourism has boomed here recently thanks to an unlikely and incongruous source: its fictional role, in Stephenie Meyer’s Twilight novels, as the home of a 3000-year-old vampire coven known as the Volturi; the tourist office proffers a walking trail of vampire-related sites.

Volterra’s alabaster

A form of crystallized chalk that has a delicate, milky texture, alabaster lends itself to the sculpture of fine, flowing lines and close ornamental detail. Even in quite large blocks, it is translucent. The Etruscans and Romans extensively mined Volterra’s alabaster for sculpting. Until the 1960s, large alabaster factories were scattered throughout the town centre, but – not least because of the quantity of dust they threw up – large-scale production was moved to outlying areas. These days, only about a dozen artisans are permitted to maintain workshops in the town centre, and Volterra’s famous art school is the only one in Europe to train students to work alabaster.

Arezzo Province

Upstream from Florence, is the Arno valley - a fairly industrialised district with warehouses and factories lining the main roads and railways. Some of the villages up on the valley retain a medieval square and attractive buildings, but the main attraction is the bourgeois city of Arezzo. With one of the most photogenic squares in central Italy and the famous fresco cycle from Piero della Francesca, Arezzo makes for a great day trip. Add on the neighbouring stops of Monterchi and Sansepolcro, to see more about the artist Piero della Francesca.

To the south of Arezzo stretches the agricultural plains of the Valdichiana. Here you can visit the ancient and lofty hill-town of Cortona to experience Frances Mayes’ ‘Under the Tuscan Sun’ expat dream. It attracts thousands of tourists every summer, but the steep little streets and tight-knit local community hasn’t lost its charm yet.

Southern Tuscany

The inland hills of southern Tuscany display the region at its best, an infinite gradation of trees and vineyards that encompasses the depopulated crete before climbing into the hills around Monte Amiata. Southwest of Siena towards the sea, the memorable but little-visited hill-town of Massa Marittima presides over a marshy coastal plain. Magnificent monastic architecture survives in the tranquil settings of San Galgano and, further east, Monte Oliveto Maggiore, which also boasts some marvellous frescoes.

The finest of the hill-towns to the south of Siena is Montepulciano, with its superb wines and an ensemble of Renaissance architecture that rivals neighbouring Pienza.

Further south, the tourist crush is noticeably eased in smaller towns and villages that are often overlooked by visitors gorged on Florentine art and Sienese countryside. Wild Monte Amiata offers scenic mountain walks, while the isolated, dramatic medieval town of Pitigliano nurtures the amazing story – and scant remains – of what was once Tuscany’s strongest Jewish community.

Massa Marittima

The road south from Volterra over the mountains to Massa Marittma is scenically magnificent yet little explored: classic Tuscan countryside which is given an added surreal quality around Larderello by the presence of soffioni (hot steam geysers), huge silver pipes snaking across the fields, and sulphurous smoke rising from chimneys amid the foliage.

Like Volterra, Massa has been a wealthy mining town since Etruscan times. The outskirts of Massa have been marred by modern development, but the medieval town itself at the top of the hill, divided between two very distinct levels, remains a splendid ensemble. While visitor numbers are much lower than, say, San Gimignano, Massa is the closest hill-town to several coastal resorts, and on summer evenings it fills up with beach-based day-trippers.


The tiny, perfectly preserved village of Pienza, 11km west of Montepulciano, is as complete a Renaissance creation as any in Italy, established as a Utopian “New Town”, in an act of considerable vanity, by Pope Pius II. A scion of the leading family of what was formerly Cortignano, he set about transforming his birthplace in 1459, under the architect Bernardo Rossellino. The cost was astronomical, but the cathedral, papal and bishop’s palaces, and the core of a town (renamed in Pius’s honour), were completed in just three years. Pius lived just two more years, and of his successors only his nephew paid Pienza any regard: intended to spread across the hill, the planned city remained village-sized. Today, despite the large number of visitors, it still has an air of emptiness and folly: a natural stage-set, where Zeffirelli filmed Romeo and Juliet.

Bagno Vignoni

The extraordinary ancient site of Bagno Vignoni is tucked away 6km southeast of San Quirico. Its central square is entirely taken up by an arcaded Roman piscina, or open pool; the springs still bubble up at a steamy 51°C, with a backdrop of the Tuscan hills and Renaissance loggia – built by the Medici, who, like St Catherine of Siena, took the sulphur cure here. Bathing in the piscina itself is forbidden, but you can still take the waters at the sulphur springs below the village (30°C), or wallow in the mineral-rich waters of one of the nearby spas (advance booking necessary).


Tuscany’s deep south, on the Lazio border, is its least visited corner. Pitigliano, the area’s largest town, is best approached along the road from Manciano, 15km west. As you draw close, the town soars above you on a spectacular outcrop of tufa, its quarters linked by the arches of an immense aqueduct. Etruscan tombs honeycomb the cliffs, but the town was known for centuries for its flourishing Jewish community. Today it has a slightly grim grandeur, owing to its mighty fortress and the tall and largely unaltered alleys of the old Jewish ghetto.

Abbazia di Monte Oliveto Maggiore

Tuscany’s grandest monastery – the Abbazia di Monte Oliveto Maggiore, renowned for its absorbing Renaissance frescoes – stands 26km southeast of Siena, or roughly 50km east of San Galgano, in a secluded but exceptionally beautiful tract of countryside.

When Pius II visited in 1463, it was the overall scene that impressed him: the architecture, in honey-coloured Sienese brick, merging into the woods and gardens that the Olivetan or White Benedictine monks had created from the eroded hills of the crete. The pope recognized the order within six years, and over the following two centuries this, their principal house, was transformed into one of the most powerful monasteries in the land. Only in 1810, when the monastery was suppressed by Napoleon, did it fall from influence. Today it’s maintained by a small group of Olivetan monks, who supplement their state income with a high-tech centre for the restoration of ancient books.

The abbey complex

From the gatehouse, an avenue of cypresses leads to the abbey. Signs at the bottom of the slope direct you along a walk to Blessed Bernardo’s grotto – a chapel built on the site where the founder lived as a hermit.

The abbey is a huge complex, though much of it remains off-limits to visitors. The entrance leads to the Chiostro Grande, where the cloister walls are covered by frescoes that depict the Life of St Benedict, the founder of Christian monasticism. The fresco cycle, which begins on the east wall, immediately to the left of worshippers emerging from the church itself, was started in 1497 by Luca Signorelli, who painted nine panels in the middle of the series that start with the depiction of a collapsing house. The colourful Antonio Bazzi, known as Il Sodoma, painted the remaining 27 scenes between 1505 and 1508. He was by all accounts a lively presence, bringing with him part of his menagerie of pets, which included badgers, depicted at his feet in a self-portrait in the third panel. There’s a sensuality in many of the secular figures, especially the young men – as befits the artist’s nickname – but also the “evil women” (originally nudes, until the abbot protested).

The church was given a Baroque remodelling in the eighteenth century and some superb stained-glass in the twentieth. Its main treasure is the choir stalls, inlaid by Giovanni di Verona and others with architectural, landscape and domestic scenes (including a nod to Sodoma’s pets with a cat in a window). Stairs lead from the cloister up to the library, again with carving by Giovanni; sadly, it has had to be viewed from the door since the theft of sixteen of its twenty codices in 1975.

Abbazia di San Galgano

The Abbazia di San Galgano, surrounded by majestic fields of sunflowers in a peaceful rural setting 26km northeast of Massa Marittima, is perhaps the most evocative Gothic building in all Italy – roofless, with grass for a floor in the nave, nebulous patches of fresco amid the vegetation, and panoramas of the sky, clouds and hills through a rose window. The main appeal of the abbey is its general state of ruin, although the basic structure has been stabilized. In summer, it makes a wonderful open-air venue for opera performances, staged on various evenings between late June and the end of July.

Eastern Tuscany

The Valdarno (Arno Valley) upstream from Florence is a heavily industrialized tract, with no compelling stop before you reach the provincial capital, Arezzo, which is visited by foreigners in their thousands for its Piero della Francesca frescoes, and by Italians in even greater numbers for its antiques trade. South of Arezzo is the ancient hill-town of Cortona, whose picturesquely steep streets and sense of hilltop isolation make it an irresistible place for a stopover.

The Maremma

The one area where Tuscany fails to impress is its over-developed coast, with horrible beach-umbrella compounds filling every last scrap of sand. Elba, the largest of several Tuscan islands, offers great beaches and good hiking, but is busy in summer.

The Tuscan shoreline is at its best in the Maremma region; the name derives from Marittima, referring to the coastal strip and inland hills of the Provincia di Grosseto, Tuscany’s southernmost province. The northern heartland of the Etruscans, this became depopulated in the Middle Ages after wars disrupted the drainage schemes and allowed malarial swamps to build up behind the dunes. The area became almost synonymous with disease, and nineteenth-century guides advised strongly against a visit – even so, butteri cowboys roamed freely then, as now, taking care of the region’s half-feral horses and its celebrated white cattle. Today, the provincial capital of Grosseto remains uninspiring, though there are some patches of fine scenery – notably the Monti dell’Uccellina, protected in the Parco Regionale della Maremma, and the wooded peninsula of Monte Argentario.

Best time to visit Tuscany

Midsummer in central Italy is not as pleasant an experience as you might imagine: the heat in the summer months can be stifling. From May to September the big tourist hotspots of Florence, Siena and San Gimingnano are too crowded to be really enjoyable.

It at all possible, avoid August, when the majority of Italians take their holidays. This means that some restaurants and hotels close, and the beaches are jam packed.

The best time to visit Tuscany is before Easter or in the late autumn. The main towns are quieter then and the countryside is blossoming or going into harvest season. The best time to see the fields of sunflowers bloom in Tuscany is in June or July.

Winter is often quite rainy, and temperatures can drop, particularly in the hill-towns. This does, however, make it a good time to visit all the cities and major art trails.

Tuscan cuisine

Tuscan cooking, with its emphasis on simple dishes using fresh, quality, local ingredients, has had a seminal influence on Italian cuisine. Classic Tuscan antipasti are peasant fare: bruschetta is stale bread, toasted and dressed with oil and garlic; crostini is toast and pâté. Olive oil is the essential flavouring, used as a dressing for salads, a medium for frying and to drizzle over bread or vegetables and into soups and stews just before serving.

Soups are very popular – Tuscan menus always include either ribollita, a hearty stew of vegetables, beans and chunks of bread, or zuppa di farro, a thick soup with spelt (a barley-like grain). Pappa col pomodoro (bread and tomato soup) is also good, while fish restaurants serve cacciucco, a spiced fish and seafood soup. White cannellini beans (fagioli) are another favourite, turning up in salads, with pasta (tuoni e lampo), with sausages in a stew (fagioli all’uccelletto), or just dressed with olive oil. Tuscany is not known for its pasta, but many towns in the south serve pici, thick, hand-rolled spaghetti with toasted breadcrumbs. Meat is kept plain, often grilled, and Florentines profess to liking nothing better than a good bistecca alla fiorentina (rare char-grilled steak), or the simple rustic dishes of arista (roast pork loin stuffed with rosemary and garlic) or pollo alla diavola (chicken flattened, marinated and then grilled with herbs). Hunters’ fare such as cinghiale (wild boar) and coniglio (rabbit) often turns up in hill-town trattorias.

Spinach is often married with ricotta and gnocchi, used as a pasta filling, and in crespoline (pancakes) or between two chunks of focaccia and eaten as a snack. Sheep’s milk pecorino is the most widespread Tuscan cheese (best in Pienza), but the most famous is the oval marzolino from the Chianti region, which is eaten either fresh or ripened. Dessert menus will often include cantuccini, hard, almond-flavoured biscuits to be dipped in a glass of Vinsanto (sweet dessert wine); Siena is the main source of sweet treats, including almond macaroons and panforte, a rich and very dense cake full of nuts and fruit.

Tuscany has some of Italy’s finest wines. Three top names, which all bear the exclusive DOCG mark (and price tags to match), are Chianti Classico, Brunello di Montalcino and Vino Nobile di Montepulciano – not the sort of thing you’d knock back at a trattoria. There are dozens of other Chianti varieties, most of them excellent, but it can be difficult to find a bargain. Both Montalcino and Montepulciano produce rosso varieties that are more pocket-friendly, and other names to look for include Carmignano and Rosso delle Colline Lucchesi. Two notable whites are dry Vernaccia di San Gimignano and the fresh Galestro.

Top image: City postcard view and towers of San Gimignano, small medieval town in Tuscany, Italy © Vaflya/Shutterstock

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updated 9/3/2021
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