The Classic Tuscany Road Trip Itinerary

The rolling hills and teetering hilltop villages of Tuscany were made to be explored on wheels. This Tuscany road trip itinerary will guide your way, but be warned, it’ll be all too tempting to dive off the road in search of la dolce vita.

Ease that campervan into first gear and savour the freedom of the open road as you explore Italy’s most characterful regions – rushing would be a sin. Sentinel cypress trees line sprawling groves of olive trees.

Tuscan farmhouses in an artist’s palette of ochre, terracotta and umber dot the landscape. Punctuating this idyllic rural setting are ancient towns and cities that if anything, are even more captivating than the countryside, and it’s easy to see why so many great artists made the region their home.

Pop on some Andrea Bocelli – scenery this big needs a big voice – wind down the windows and let the scent of rosemary, sage and fragrant wisteria fill your van and your lungs.

Begin your Tuscan adventure in elegant Florence. The birthplace of the Renaissance, your feet will pound the same stone pavements as once did those belonging to Leonardo da Vinci, Botticelli, Michelangelo, and Donatello. Such venerated architecture lends itself to aimless wandering and there’s much to be said for unhurried strolls in the city’s historic core. 

Dip into the Uffizi and Accademia galleries on a pre-booked ticket – who wants to spend their precious holiday in a queue? Make a beeline for the city’s 13th-century cathedral, its green, white and pink marble reminiscent of nougat and just as delicious.

Pause for gelato, of course.

The names you’ll want to remember are Vivoli, tucked down a backstreet near the Piazza Santa Croce, and Grom, whose queues snake round the block. As the sun sets, seek out the River Arno.

Tick off the Ponte Vecchio, where the butchers’ shops once clustered, drawn by the convenience of chucking rancid scraps into the water at the end of the day. It’s more civilised now, occupied by jewellers since the time of Ferdinando I De’ Medici. Join the passeggiata along its banks before indulging in a long, leisurely dinner.

Inspired? Take a cookery class before you leave so you can recreate the dishes back home.

Take the Chiantigiana road, known to your sat nav as the SR222, one of Tuscany’s most scenic drives. Winding roads make a necklace of the region’s village jewels – Greve in Chianti, Panzano, Castellina in Chianti. Don’t be afraid to take a circuitous route, with Montefioralle and Radda in Chianti being most worthy of a detour.

It’s wine country, if you hadn’t worked it out. Flip a coin to figure out who’ll be the designated driver today as you make your way to Siena, and who will take a turn tomorrow. 

Embrace this city where a square is a semi-circle and sometimes the chairs and tables from countless pavement cafés are cleared to make way for a thrilling horse race.

Mediaeval Siena is never far from the surface: filter out the souvenir stalls and coffee shops and let your mind imagine how it would have been. Begin in the middle and at the edge of Piazza del Campo you’ll find the 13th century Palazzo Pubblico, the city’s town hall.

Check out ceiling frescoes designed by Domenico Beccafumi in the Sala del Concistoro which paint a positive picture of the city’s mediaeval government. Work up an appetite climbing the 400 or 500 steps (who’s counting?) to the top of Torre del Mangia. Take a leaf out of its first bell ringer’s book and pile the calories back on with lunch in the square.

Make time for a trip to the city’s Duomo, Santa Maria Assunta, and the Piccolomini library, located inside. Wrap up the day looking after your stomach: grab an aperitivo at the charitable Caffé la Pizzetta, dine on hare or wild boar in the atmospheric surroundings of Antica Osteria da Divo and sip late night cocktails at Cacio e Pere, known for its live music.

From Siena, it’s a short drive to charming San Gimignano via the delightful countryside. This too is Chianti country, so play nice and swap over at the wheel.

Call in at the Tenuta Torciano winery, just north of the town and take a tour of the Giachi family’s vineyard. Poggioaicieli wines, created from the local Vernaccia di San Gimignano grape, have been their speciality for the past two decades; the quirky spiral layout of the vines is another talking point.

Taste the wine and learn about its production in the company of an experienced guide and settle down for a slap-up lunch. 

Afterwards, pootle into San Gimignano and park up. Where once there were 72 stone towers, now there are fourteen, but that’s still enough to wow. Dating from the 13th and 14th century, they were built as a display of wealth by the town’s well-heeled residents. Walk the walls and visit the cathedral.

A liberal scattering of piazzas provide characterful cafés when your feet are in need of a break, perfect for people watching. Before sunset, climb the Torre Chigi at the Useppi Palace to take in the views across the Tuscan countryside. As the light fades, dinner is served.

Take the long way to Pisa, looping via the SP1, SP62 and SP15 to tag on a trip to Volterra passing obscenely pretty olive groves and steep clay hills known locally as balze along the way.

So much more than a tower with a list, Pisa is a vibrant university town with a seductive personality. Within the Piazza dei Miracoli, or Square of Miracles, duck inside the imposing cathedral (the Leaning Tower is its bell tower), test out the acoustics of the Baptistry and take a stroll inside the Campo Santo cemetery. 

Touristy though it is, the Leaning Tower is a must, though its slippery, well-trodden marble steps and pronounced slant can leave you feeling like the effects of yesterday’s Chianti haven’t quite worn off. Get your bearings from the viewing platform at the top before you descend to make your way in the direction of the River Arno.

Don’t miss the Piazza dei Cavalieriat the school Napoleon founded, Scuola Normale Superiore, as well as the house where scientist Galileo Galilei was born.

Continue your Tuscany road trip and wind up by the river at the University of Pisa, one of Europe’s oldest, before ducking back into its labyrinthine streets to chow down with the locals on hearty fare like pici (fat noodles), meatballs or baked cod.