Road Tripping Tuscany: 13 Enchanting Stops Along the Way

Richard Francis

London, UK

Oh, Tuscany! The stuff of Italian dreams, this region rarely fails to enchant. Sweeping from the Apuan Alps to the verdant valleys of Maremma and the sloshing waves of the Ligurian Sea, it covers some seriously gorgeous corners of the land (and is home to some of the best things to do in Italy). The backcountry is a mosaic woven from the threads of old Etruscan villages and steaming hot springs, of winelands with famous grapes and soft farms blanketed in sun-baked hay. Luxury villas mix and mingle with haunting churches and ruined barns. The towns either burst with art (just check out Florence) or tick over with the slow pace of the backcountry. This guide weaves and wiggles through the lot, helping you pinpoint 13 places in Tuscany, Italy, that you simply have to add to your itinerary.

Castle-topped Minucciano and mountain-shrouded Gorfigliano

Minucciano, Minucciano
Minucciano, Tuscany, Italy.

At the north end of Tuscany, you’ll enter a mist-shrouded land of high peaks and deep valleys. This is the Apuan Alps. It’s hardly how you imagine the region, with deep forests of chestnut and oak and hornbeam cascading down from summits of gnarled marble. High up, along hair-pinning bends, little Minucciano crowns one peak. It took its name from a Roman consul and has a roundhouse castle turret at its center. Keep driving into the next valley and there’s Lago di Gramolazzo, perfect for a pizza and wild swim. Next up is Gorfigliano. It sits on the cusp of the Apuan Alps Park where you can hike on untrodden trails to lookouts over Carrara marble quarries and even the Ligurian Sea!

Walk the walls of Lucca

Lucca, Lucca
Lucca, Tuscany, Italy.

Once powerful enough to rival even Venice, Lucca stands at the gateway to the Tuscan plains on the south side of the Apuan Alps. It’s ringed by mighty walls, a creation of the Renaissance that can still be strolled to see formidable brick bastions and gatehouses. They demark the historic center, which is a joy to get lost in. Follow Via Fillungo to the soaring clocktower and you’ll pass close to the grand Ducal Palace and the fantastical façades of the Duomo di San Martino. When you tire of sightseeing, set aside some time for a crisp Colline Lucchesi wine and a plate of Matuffi: a local dish that’s all polenta, wild mushrooms, and Italian sausage.

Shorten the bucket list in Florence

Florence, Florence
Florence, Tuscany, Italy.

No ultimate bucket list for Tuscany, Italy, could possibly be complete without at least a nod towards the region’s glorious capital. It might be better to make it a little more than a nod, though. This city is positively brimming at the Renaissance seams with artistic treasures and amazing tales. The obvious highlights are the inlaid marble Duomo and the Uffizi Gallery, where you’ll discover pieces by Michelangelo and da Vinci’s Adoration of the Magi. However, you could also hit the Museo Galileo to uncover the innovative discoveries made by one of Italy’s finest. And there are awesome lookouts up on the Giardino Bardini with views that encompass the Arno River, the Ponte Vecchio, and the hills of Arezzo.

Be stunned by uber-romantic San Gimignano

San Gimignano, San Gimignano
San Gimignano, Tuscany, Italy.

Some say that San Gimignano is the most handsome town in the world, let alone only in Tuscany. Like a sprinkling of cinnamon between the cypresses, it’s draped over the low hills right in the heart of the region. It started as a small Etruscan settlement in the third century AD, but became powerful as a pilgrim’s stopover on the route to Rome. Warring families during the 13th and 14th centuries competed to create the highest towers in the center, which is why soaring summits crash above the piazzas. These days, though, tribal conflicts are put aside in favor of legendary gastronomy. From porchetta to saffron rice and crisp white wines, there’s all sorts on offer in the cozy local trattoria.

Hidden hill town charms in Colle di Val d’Elsa

Colle di Val d'Elsa, Colle di Val d'Elsa
Colle di Val d’Elsa, Tuscany, Italy.

You might not believe it when you finally see it, but Colle di Val d’Elsa is one of Tuscany’s hidden gems. Crowning a long ridge in the province of Siena, it’s a sumptuous showcasing of terracotta roofs and honey-tinged walls. Be sure to park the car in the new town and use the lifts that are built straight into the mountain to get up top. Then, you’re onto cobbled lanes draped with bougainvillea, where glass-blowing workshops and osterias beckon down the back alleys. A highlight here has to be the gorgeous view of the Chianti Valley that sweeps southwards. It’s classic Tuscany; think slender cypresses and dashes of verdant vineyards.

Siena: the home of the iconic Palio

Siena, Siena
Siena, Tuscany, Italy.

Siena was once one of Italy’s proudest city states. From the 1200s to the 1550s it waged wars with Florence and Spain alike. The conflicts, and outbreaks of the Black Death, took their toll, though, and the town soon fell into obscurity. That is, until now. These days, it’s hailed as a window into the glorious past of a doomed republic. Redbrick towers clamber overhead. The Siena Duomo has more filigrees and fusions of architectural styles – from Classical allusions to touches of Parisian Gothic – than you can shake a Chianti red at. And if you’re lucky enough to be passing through in August, you won’t want to miss the Palio. It’s an adrenaline-pumping horse race that takes place on the oval Piazza del Campo each summer.

Go bathing in the steaming riverways of Bagni di Petriolo

Bagni di Petriolo, Bagni di Petriolo
Bagni di Petriolo, Tuscany, Italy.

Hot springs are everywhere in Tuscany. Like one great big open-air spa, the region offers up bubbling pools and steaming water channels all over, each powered by fumaroles and volcanic movements beneath the surface. Bagni di Petriolo is one of the chart-topping options to consider. It’s unique for its mineral-rich waters that gush from the earth at a soothing 109 degrees. They drop over calcite rocks and straight into the Farma River. Makeshift pools surrounded by boulders have been built to create free bathing spots there. As you lay, try to peer through the woods to see the ruins of the ancient Roman bathhouses – Petriolo has been on the spa map of Italy for thousands of years!

Wine, wine, more wine, and oodles of food in Montepulciano

Montepulciano, Montepulciano
Montepulciano, Tuscany, Italy.

Montepulciano is hallowed territory in the world of wine lovers. The rich Vino Nobile that is plucked from the aged vines here is famed around the globe for its sprightly and refreshing taste, fusing red berries and plum in blends of Sangiovese grapes. But before you taste yourself into a stupor, there’s a town to see! Yep, Montepulciano is way more than just a viticulture hub. It’s a gorgeous medieval center with streets that weave and wind around crenulated towers, sometimes opening to views of the Val di Chiana, other times descending into underground trattoria scented with truffle and cheese.

Quintessential Tuscany on the piazzas of Sarteano

Sarteano, Sarteano
Sarteano, Tuscany, Italy.

Small Sarteano sits on a hilltop above plains scattered with wineries and rustic farms. It’s marked out by its colossal castle, which sprouts from a forest over the narrow alleys and steeply sloping streets below. After scrambling to the bulwarks and drawbridge in the citadel, you can head back to the main piazza to reward yourself with a stacked gelato and coffee. On weekends, a rural market erupts in the center. It’s a people watching mecca, filled with stalls scented with wild porcini mushrooms and pecorino cheeses.

Unravel tales of the Italian Robin Hood in Radicofani

Radicofani, Radicofani
Radicofani, Tuscany, Italy.

Radicofani is marked out by the soaring tower of its great citadel. It’s at least 1,000 years old and once featured as an important defensive barrier between the Pope’s territory and Tuscany. However, the most romantic tale of the castle comes with Ghino di Tacco. He’s a mysterious, swashbuckling figure who’s hailed as the Italian Robin Hood. The so-called brigante buono (the good brigand) holed up in Radicofani’s keep while he raided nearby towns and villages, always leaving his victims something to survive on. Beneath his onetime base, you can wander handsome Radicofani itself, where stone-faced cottages spill onto flower-strewn squares.

Meet the White Whale of Bagni San Filippo

Bagni San Filippo, Bagni San Filippo
 Bagni San Filippo, Tuscany, Italy.

Bagni San Filippo hosts yet another selection of natural warm-water springs. It’s a small town, huddled onto a hillside just at the western edge of the Val d’Orcia. The steamy waters submerge the whole place in a lightly sulfuric air, which says the bathing spots are never too far away. Be sure to skip the paid thermal baths and walk straight into the forest park just a few minutes out of the center. Down a short track overshadowed with downy oaks and pines, you’ll find the so-called White Whale. It’s a hulking mass of calcium deposits that have built up from centuries of water trickles. Beneath it are the muddy spa pools. They’re free to enter and offer natural face masks next to soothing waterfalls.

Cruise through the heart of the Val d’Orcia

Via Val d'Orcia, Roma
Val d’Orcia, Tuscany, Italy.

If you’ve ever seen a postcard of rural Tuscany, Italy, there’s a high chance it was a shot of the Val d’Orcia. Sinews of chalk rock punctate the landscapes. There are taupe fields speckled with rolled hay. There are oak woodlands that crawl up mountainsides, occasionally dotted by half-ruined farmhouses just waiting to be converted into villas. The gateway to it all is Pienza: a city constructed by Pope Pius II to be the Renaissance utopia. The nearby Chapel Vitaleta is a stunning stop for budding photographers, but the beautiful SP-18 going south is the road to take for a montage of vineyards, soft hills, and agritourisms that serve regional wine and produce.

A bath in the open air to finish things off at Terme di Saturnia

Terme di Saturnia, Terme di Saturnia
Terme di Saturnia, Tuscany, Italy.

Nestled in the rural lands of Maremma in southern Tuscany, where the olive groves finally tumble into the Mediterranean Sea, the babbling springs of the Terme di Saturnia are one of the region’s headline acts. Gurgling up from the earth in a series of hot-water cascades, they drop over terraced rocks at the Cascate del Mulino. You can discard the clothes and hop right in, where you’ll laze in 98-degree water while surveying the countryside, its gallery woods of chestnut trees, and soft fields punctuated by brick barns. The H20 here is said to have all sorts of healing properties, from respiration repair to aromatherapy and more. It might just be the perfect way to unwind after a road trip through the heart of Italy.