By Ferenc Máté
January 02, 2015
Rod Edwards / Alamy

The back roads of Tuscany are a dream for anyone who has uttered the word “sports car.” Most of the roads here follow every dip and curve of the hilly, pastoral landscape— because even though they’re perfectly paved now, they were born as mule trails 2,000 years ago. Even in world-famous areas like Chianti, the roads have a single lane in each direction, and are banked like a racetrack on every curve. The traffic on them is virtually non-existent; on some you might even suffer from loneliness. And each crest will bring you a scene dreamier than the last: castles, ancient farmhouses, vineyards, and fields of poppies.

If you’re considering a splurge, this may be the time to rent a small convertible. No need for a Maserati; a Fiat Cinquecento is more fun. Either race the route or crawl and gaze in endless awe. After 25 years here, I still do.

The only quandary you may face when day tripping around Tuscany is, as always, food. Where to lunch? The most genuine (and flavorful) food is found in tiny restaurants in the most out of the way places, yet I’m always torn between them, and packing a picnic basket full of fresh bread, cheeses, cured meats, and of course, a bottle of wine and a blanket for stretching out on a hilltop. Oh life! To picnic, or not to picnic, that is the question.

Note: when, in the following directions, I write “to Pienza” that “to” means stop and visit town. When I write “through Torrenieri” the “through” means hit the gas and keep going.

Now get out your Tuscany road map and follow me!

Le Crete Senesi

Stark and haunting, this enormous landscape sculpture is possibly the most dramatic and silent in all of Tuscany. From Siena, take a quick road to Taverne D’Arbia and turn to Asciano. From here, there are two narrow roads to Chiusure—take one going and the other coming back. Stop at Chiusure and have a glass of wine at Il Paradiso, and gaze at the endless hills. Move on to San Giovanni D’Asso, with its magical Romanesque little church, then through Torrenieri, to Buonconvento. Do plan a long stop at Abbazia di Monte Oliveto Maggiore. There is a wonderful trattoria next to the abbey—best in truffle season, October to January. Tour the abbey with its thirty-two giant frescoes and magnificent library, then head back to Asciano on the road you didn’t come on. Stop to watch the sunset. You’ll thank me profusely.

A Fairy Tale

From Montepulciano, the most impressive Tuscan hill town, head to Pienza (the most romantic hill town). Continue on to San Quirico though the bucolic landscape, and be sure to savor each curve and view. Take old road from San Quirico to Torrenieri, then east to San Giovanni D’Asso. Head on to Montisi on a wonderful ridge road, then to Castelmuzio—my favorite Tuscan village. Have lunch in the piazza (five tables, great soups); then drift to Petroio and walk its corkscrew streets. Stop in Montefollonico, then head back to Montepulciano.

All Alone

The most visually impressive and romantic area of Tuscany is the Val D’Orcia: the valley of the Orcia River. It was declared a UNESCO World Heritage Site, and your first glance will tell you why. For millennia man has worked this hilly land turning it into a vast, sensuous, harmonious paradise. If there was ever a perfect symbiosis between man and nature, this is it. Best to have a bottle of wine with you and stop often.

From Pienza, head south then turn left to village of Montechiello, one of Tuscany’s most stunning, miniature worlds (all of it 600 years old and delicately restored). Double back toward Pienza, but turn south to Radicofani to stuff yourself with lunch at La Grotta. Then continue to Bagno San Filipo and soak under hot cascades of the thermal baths. You’ll be enormously relaxed as you head on to Castiglione d’Orcia, with its spectacular views from the tower, then on to San Querico and Pienza. Do visit every town. This is a long day trip; if you want to break it up, every town I mentioned is perfect for an overnighter.

The Wine Route

If you are a lover of wine and want to drive through the best zone for wine tasting, this trip is for you. From Montalcino head to Castelnuovo dell’Abate. Visit the radiant travertine and alabaster church of Sant’Antimo, where the daily mass includes haunting Gregorian chants. Head east to hidden Seggiano, then Castel del Piano, then Arcidosso. Lunch at La Tagliola, a tiny restaurant at the end of nowhere, with porcini mushrooms cooked ten different ways. Continue on to Monticello Amiata, Cinigiano, and Castel Porrona; then head back to Montalcino for sunset.

Wildest Tuscany

The southern part of Tuscany, divided from the north by the great volcano Monte Amiata, is even more pastoral than the rest. Rugged, wild, almost untouched for centuries, it has retained its original charm, country life, amazing food, and human pace. Expect solitude and vast vistas.

From Montalcino, head to Sant’Angelo in Colle. Pass through Sant’Angelo Scalo (take a side trip to Castello Banfi and its museum), then on to Arcidosso and Roccalbegna. Visit the dramatic outlook, then stuff yourself with a unique lunch at La Pietra, where most of the vegetables, olive oil, and wine are made in-house. Continue on to the strange long town of Cana, then to Stribugliano and the great views from Castiglioncello Bandini. End up at Sant’Angelo in Colle for a stunning sunset.