Top 7 Tuscany highlights

Italy’s loveliest hill towns, sweeping landscapes, endless food and the world’s finest Renaissance art: Tuscany has it all. Here’s how to see the very best on your holiday
Landscape panorama, hills and meadow, Tuscany, Italy
Tucany, Italy

Landscape panorama, hills and meadow, Tuscany, Italy. Photo: ronnybas / Shutterstock

1. Val d’Orcia landscape

The Val d'Orcia is a beguiling rural area south of Le Crete, but within sight of hulking Monte Amiata. With its farmhouses, abbeys and conical hills, this pastoral landscape was redrawn in the 14th and 15th centuries to reflect good governance and create an aesthetically pleasing picture that has inspired many artists. 

Villages are scattered across the countryside, many of which suffered from depopulation in the 1950s but are now reaping the benefits of an intact urban and rural landscape. In the area are three medieval fortresses: Ripa d'Orcia, Rocca d'Orcia and Castiglione d'Orcia. At each, you'll find atmospheric ruins and wonderful views. 

2. San Gimignano

Famous for the sculptural quality of its skyline, San Gimignano is a spectacular sight. It may be a cliché to call this hill town a “Medieval Manhattan”, but the famous towers do resemble miniature skyscrapers. Seen from inside, it is the unspoilt townscape that bowls you over: almost nothing seems to have changed since the Middle Ages. See it for yourself: Talk to our Italy travel experts now to plan your unforgettable holiday.

In its heyday, the city had a total of 76 towers, only 14 of which remain. After San Gimignano fell under Florentine control, it became an economic backwater, bypassed by the Renaissance – for which we are eternally grateful. The towers alone make a visit here worthwhile, but the town abounds in quirky sights, even if staying overnight is the only way to appreciate them in peace. 

The medieval town of San Gimignano.San Gimignano: a 'Medieval Manhattan'

3. The Leaning Tower of Pisa

Finally fully restored, this iconic symbol of Tuscan architectural genius stands alongside the gleaming Duomo and Baptistery on the aptly named Campo dei Miracoli – the Field of Miracles.

Visitors flock to Pisa from all over the world to marvel at the phenomenon of the Torre Pendente. The best place to catch your first sight is through the archway of the Porta Santa Maria, otherwise known as the Porta Nuova. When the sun is shining, the whiteness dazzles; when raining, it glistens. Visit Pisa as part of Insight Guides' From Venice to Florence: A Grand Tour of Northern Italy trip, or on our Treasures of Italy: Venice, Florence and Rome trip

4. Hill towns Montepulciano and Montalcino

The route through the dramatic Crete region delivers you to the heart and soul of Tuscany. Montepulciano and Montalcino draw you in with their palaces, seductive lifestyle and cellars of famed wines. 

Montepulciano's asymmetrical design and spontaneous development give it the architectural tension that some Tuscan towns lack. Just outside and below the city walls, at the end of a long line of cypresses (of course!), lies the Sangallo's San Biagio, the Renaissance church. The building's isolation focuses attention on the honey-coloured travertine, the Greek Cross design, the dome and the purity of the line. The airy interior has a deeply classical feel, more akin to the Roman Pantheon than to a small Tuscan church. 

Montalcino, on the other hand, is certainly the most Sienese town in the province. In essence, its history is a microcosm of Sienese history. The town's magnificent 14th-century Fortezza is the key to Montalcino's pride. The approach is through olive groves and the slopes famous for Brunello wine, but it's the town's impressive fortress that captures your attention and dominates the landscape. Explore them both with a tailor-made trip to Tuscany

5. Tuscan spas

Despite dating back to Etruscan times, Tuscany’s new breed of thermal spas combine sophisticated pampering with authentic water cures in incomparable natural settings.

But, never fear, the scary white-coat brigade has been banished from the best Tuscan spas, such as Chianciano’s Terme Sensoriali, one of the most approachable yet seductive day spas.

Neighbouring Fonteverde, floating on a sea of hills in Val d’Orcia, is a terraced spa resort clustered around a late Renaissance villa. The stylishly simple estate is dotted with thermal pools but, as a destination spa, also delivers oriental massage, skin consultations, dietary advice, yoga and spiritual healing – all presented clearly, without pushiness or psychobabble. Sound like your thing? Have one of our experts plan a tailor-made trip based around the Tuscan spas

Piazza del Campo, Siena, Italy.Piazza del Campo, Siena, Italy. Photo: stefano marinari / Shutterstock

6. Wine tasting in Chianti

Ignore the “Chiantishire” tag and visit a chequered landscape of vineyards, villages and fortified-wine estates that include the Castello di Brolio, birthplace of the modern Chianti industry. For all its history, Tuscany remains at the forefront of the wine industry, which is still dominated by many of the original noble families.

Situated between Florence and Siena, the Chianti Classico heartland includes Barberino Val d’Elsa, Castellina, Greve, Gaiole, and San Casciano. However, the top Tuscan red is arguably Brunello di Montalcino, made from Sangiovese grapes grown on hillsides south of Siena. Brunello is a powerful yet refined red that ages superbly, with Rosso di Montalcino its more approachable younger sister, and the “princely” Vino Nobile di Montepulciano, loved by princes and popes since Medici times. Let one of our local experts plan a trip to Chianti for you, just get in touch and let us know how long you want to go for, and we'll do the rest. 

7. Siena, the quintessential medieval city

From its striped marble Cathedral to its tunnelled alleys, brilliant Campo and black-and-white city emblem, Siena is a chiaroscuro city. In its surging towers it is truly Gothic. Where Florence is boldly horizontal, Siena is soaringly vertical; where Florence has large squares and masculine statues, Siena has hidden gardens and romantic wells. Florentine art is perspective and innovation, while Sienese art is sensitivity and conservatism. Siena is often considered the feminine foil to Florentine masculinity.

For such a feminine and beautiful city, Siena has a decidedly warlike reputation, nourished by sieges, city-state rivalry and Palio battles. The pale theatricality in Sienese painting is not representative of the city or its inhabitants: the average Sienese is no ethereal Botticelli nymph, but dark, stocky and swarthy.

This article was originally published on June 19, 2016. 

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