La Dolce Vita: a road trip through Tuscany

A road trip through Tuscany reveals the unspoilt beauty of the region – and the romance of the Italian road

With luscious landscapes, legendary artworks and local delicacies, there’s a lot to love about Tuscany. For centuries this corner of Italy has attracted travellers; from bright young things embarking on the Grand Tour and 18th-century romantics, to today’s tourists looking to bask in the region’s unparalleled beauty. With hotspots like Florence and Siena congested during the peak seasons, it’s well worth hitting the road behind the wheel of something suitably stylish (and, ideally, Italian) and heading to the less populated areas to unearth some of Tuscany’s best-kept secrets. 

Choosing to do just that, I first lay eyes on my road trip steed – a vintage Alfa Romeo Spider – moments after landing at San Francesco d’Assisi Airport on the outskirts of Perugia. First released in 1966, this four-wheeled representation of la dolce vita is the definitive Italian sportscar, with its Rosso Corsa paintwork, beguiling bug eyes and streamlined silhouette. Testament to its design, the original Alfa Romeo Spider remained in production until 1994, with only slight tweaks to the styling and engineering that underpinned it.  

With keys in hand and canvas roof dropped, I head for the hills due north of the airport. After a blast up the E45 motorway, I make my way to the hills above Arezzo, aiming for a particularly picturesque converted farmhouse that will serve as my base. Once off the main motorway, I am quickly absorbed into the dense forest that occasionally gives way to vistas over long lakes and impossibly beautiful hilltop towns. It’s hard to resist pulling over on every sweeping bend to soak up the serenity and sheer beauty of a rolling landscape peppered with vines, olive trees and hilltop villages. 

Closing in on my base, high on the hilltop, the Alfa crunches its way up the steep gravel driveway to La Palazza nel Cielo, a cosy converted 200-year-old farmhouse. Once through the door, its gloriously big shuttered windows looking out onto farmland, hills and the villa’s heated infinity pool, letting light in from every angle. Built on the hillside, La Palazza nel Cielo is typical Tuscan farmhouse consisting of layers and different levels. Complete with pool, a vast games room-and-gym and six bedrooms, the well-appointed and beautifully furnished villa comfortably sleeps 14. There are even log burning stoves for the cooler months.

Settled in and unpacked, I head out on my first adventure in the Alfa, taking the twisting road down to Sansepolcro, the largest town in the Valtiberina. With a strong link to the tradition of lacemaking, this charming walled town is also an architectural and art hot spot, boasting a cathedral as well as galleries and museums housing the paintings of Perugino, Piero della Francesca to name but a few famous local painters. There’s plenty of parking outside of the town’s walls and only a short walk to the main square – sit outside in one of the many cafes and sip an espresso while locals dart around on bikes and scooters as the church bells chime on the hour. Sansepolcro is home to the Palio della Balestra – the town’s crossbow tournament – and visitors in the quieter seasons can see it on the second Sunday in September. 

Retreating back to my hilltop hideout, I prep for another, longer road trip a few days later to Montepulciano to sample some its famous wine. Setting off from the villa, the twisting road down to the valley floor proves the perfect place to enjoy some more dynamic driving in the Alfa before cutting west around Arezzo and then south. After a bast down the E35 – the spine that cuts through the heart of Tuscany – I pull off and pick up another twisty, undulating backroad, closing in on my destination of Montepulciano. Passing through more picture-postcard towns and villages, the Alfa hums down tree-lined avenues and narrow hillside passes, attracting looks from locals as I pass by. While my vintage Alfa isn’t going to offer up much of a challenge to my modern-day Ferrari, it has more than enough performance to breeze along the winding Tuscan roads. 

Approaching my destination, Montepulciano is perhaps the most striking of all Tuscan towns when viewed from the road, particularly when approaching from the south. Perched high on the hillside, the town’s imposing architecture would have made Montepulciano a formidable target for any advancing army back in the day. Now best known for its wine called Nobile di Montepulciano and the prugnolo gentile grapes used to produce it, regulations stipulate that the wine can only be produced in the municipal area of Montepulciano and can only be sold after aging for a minimum of two years and passing a series of tests carried out by a ministerial board – who said the Italians don’t take their wine seriously? 

Heading back on the road with a few bottles of Montepulciano stashed in the boot, it’s the beginning of the end to my Tuscan road trip. Skirting the shores of Parco Regionale del Lago Trasimeno on the Umbrian border on my way back to the airport, the Alfa and I have covered nearly 200 miles of east Tuscany, soaking up the sights, sounds and sun of one of Italy’s most beautiful regions. Parking up, I reluctantly hand back the keys, knowing the reality of regular life awaits. With such stunning scenery, history, architecture, art and food to find in Tuscany, there’s no better way to soak it all up than behind the wheel of a drop top Italian sportscar.

Discover more of Tempus’ travels 

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