The most scenic drives in Tuscany
Roadtripping across Italy can vary dramatically depending on the amount of time you have. If you need to make a beeline to your destination in the quickest amount of time possible, the network of the country’s Autostradas is your best bet. But if you have a more tranquil itinerary, consider the more scenic back routes, full of beautiful scenery and unforgettable villages of Tuscany. Destination expert Ondine Cohane suggests three of the best drives in the region.
For further inspiration, see our guide to Tuscany and its best hotels, restaurants and beaches and things to do.
Drive One: Capalbio to Marina di Bibbona
The Aurelia is one of Italy’s most storied roads, a thoroughfare since Roman times, bringing pilgrims and travelers up and down the coast from Rome into France. It remains one of the country’s most important routes, and is, in fact, one of the only ways to access the seaside villages.
Start your drive from Capalbio, the spectacular and little-known hill town that has been a seaside getaway for generations. From there you will follow the Aurelia (strada statale 1) north. Take the exit towards Orbetello, and the Argentario, home to Porto Ercole, where VIPs from all over the world moor their yachts. You can have lunch at the storied Hotel il Pellicano at its Pelligrill Tuscan Grill, an al fresco restaurant with views of the sea and dishes like grilled whole fresh fish. Before returning to the car, take a gander at the swimming dock made famous by iconic Slim Aarons photos.
Return to the Aurelia still heading north. You will be passing beach exits all along the way so if you get a fancy for swim you can pull into beaches by Castiglione della Pescaia, a town that overlooks beach clubs, a summer favorite for landlocked Tuscans. Just watch the speed limits here — they are strictly enforced.
Unless you are taking the ferry to Elba or other islands, bypass Piombino and continue north to San Vincenzo, a seaside resort town with bars and restaurants along its promenade. At La Perla del Mare, you can eat dishes such as grilled scallops or laze in its beach club right alongside — grab a Negroni and a day bed, and siesta as long as you like.
Alternately, for one of Italy’s best seafood restaurants in Marina di Bibbona, La Pineta offers just caught seafood and a book length wine list—don’t miss the crudo, raw fish, that’s sushi grade, and pastas like spaghetti alle vongole or bavette con calamari.
From this point on the Aurelia you are perfectly positioned for other cities not far away — towns like Lucca and Volterra, or smaller hill towns like Bolgheri. You may be sad to say goodbye to your coastal road though.
Drive Two: Siena to Bagno Vignoni
Many travelers take the A1 from Florence to Rome, but if time allows we suggest taking the Via Cassia, also known as the strada statale 2, instead. For scenery that’s truly breathtaking, even for insiders’ this is the Tuscany of postcards. It’s possible to take the route all the way from Florence and then slowly meander towards Rome, but the most fabulous stretch remains the southern stretch after Siena.
Much of the Via Cassia coincides with the pilgrims’ route known as the Via Francigena, and where pilgrims walked on part of their long trek from Canterbury to Rome. The landscapes create a spiritual feeling even in the non-religious with its unusual crete senesi, a type of clay formation, undulating green and wheat fields, sculptural like cypress trees, and protected villages.
Villages along the way demand a gander. Choose either Pienza for Renaissance perfection and pecorino cheese, which you can eat on a panino, sandwich, overlooking the Unesco-listed countryside. Pick one up at Prosit, a recent and wonderful addition to town with artisanal ingredients and kind owners. Wine lovers might instead pick Montalcino known for its Brunello wine — Osticcio Ristorante Enoteca has a fabulous list of vintages and an updated take on Tuscan classics.
A natural thermal spring nexus, Bagno Vignoni has drawn visitors since Roman times for its restorative waters and quiet atmosphere. One can enjoy the heat and then luxuriate in one of the cozy rooms at Posta Marcucci. Not far away, in the little-visited and lost in time village of Rocca d’Orcia is Osteria Perilla, a recent Michelin entry, with standouts like pigeon breast tartare and an unforgettable ravioli del plin in a slowly cooked chicken stock, perfect for wintery days.
Drive Three: Florence to Siena
Known as the 'Chiantigiana' because it runs through the famed Chianti Classico wine area, the strada regionale 222, runs through narrow winding roads, famous vineyards, and the small towns that seduced many a Brit, hence the area’s nickname, Chiantishire.
If there is only one town that you have heard of its sure to be Greve in Chianti. Try one of the area’s excellent vintages at Enoteca Falorini or try the iconic bistecca Fiorentina, T-bone steak, in front of the roaring fireplace at Villa Bordoni — the Scottish owners-transplants have recently been producing their own wine on the surrounding slopes. Meanwhile for those who like their steak with a bit of theater, head to nearby Panzano for a visit to Dario Cecchini, also known as the singing butcher. For high quality cuts and operatic antics, he put the town on the map for many.
As you continue south on the 222 the next must is Castellina in Chianti (part of the province of the Siena), an important strategic point in the battles between Siena and Florence, with Etruscan roots. Don’t miss the impressive fortress and the Archeological Museum Senese Chianti — views from the tower give you a sense of why this area had such symbolic and geographical importance. From here you can easily make your way on to Siena.
