No matter which route you choose, you could expect delicious food, wine, and superb views.
Whether coastal or country,Tuscanyis made for four wheels.
Starting in Pienza, travel south and then east to Monticchiello, a perfectly preserved 15th-century village.
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Enjoy lunch atLa Grotta, then head northwest to Bagni San Filippo to soak in the natural thermal baths.
Then, it’s on to San Quirico d’Orcia for more medieval Tuscany and great views.
On your way south to Montepulciano, stop in Montefollonico.
A vineyard in Tuscany.Christopher Larson/Travel + Leisure
Tip: You might want to break up the drive into a few days.
Every town mentioned is perfect for an overnighter.
The Wine Route
Wine loverswho love a great drive, welcome to Brunello country.
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About five minutes down the hill isPoggio di Sottofor an excellent Brunello experience.
Or, check outPodere le Ripi, whose bonsai wines and farm-to-tableTuscan Garden Experienceare a must.
Art With a Side of Vino in Chianti
What’s better than a trip filled with art?
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A trip filled with art, great food, and delicious wine.
Luckily, the Chianti countryside offers it all.
From Florence, take the winding road toAntinori nel Chianti Classicoin Bargino.
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Antinori has a rooftop restaurant Rinuccio 1180 overlooking the vineyards.
Walk, run, hike, bird-watch, or simply enjoy the dunes.
Further south lies Talamone, a picture-perfect medieval town on a wild promontory with a castle.
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it’s possible for you to explore the oasis via trail and guided tours.
Driving north or south on the E80, take the Orbetello Scalo exit.
On a rainy day, you’ll be caught up in Monte Argentario’s incredible nature.
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You’ll want to walk around the town and enjoy the pebbly beaches.
Wild Tuscany
Southern Tuscany is wild.
Divided from the north by Monte Amiata, the rugged countryside has been almost untouched for centuries.
Expect original country charm, amazing food, solitude, and vast vistas.
Next, it’s time for Stribugliano and the great views from Castiglioncello Bandini.
The landscape of lush rolling hills is at once dramatic and breathtaking.
Finally, head back to Asciano on the SP60 road.
Stop when you’re ready to take in the Val d’Asso and watch the sunset.
