Everyone who has envisioned the quintessential, dreamy sojourn to the countryside of Italy has likely considered booking tickets to Tuscany, and its charming, picturesque towns. Steeped in history and brimming with world-renowned restaurants, stunning architecture, and sweeping vistas that will likely make you want to drop everything and start a new life on a vineyard, Tuscany is one of Italy’s most unforgettable regions. And while the larger cities like Florence and Sienna, and the hotels in them like The St. Regis Florence, are worth a trip in themselves, we’ve highlighted some of the more remote towns that are worth renting a car for—and going the extra few miles.
While we can’t necessarily provide you with the tools for a full-on move to this storied region of one of Europe’s most romantic countries, we’ve got tips on the most charming and beautiful remote towns of the Tuscan countryside. From the Renaissance palaces of Montepulciano to the wall-top promenades of Lucca, here are a few towns that should absolutely make your itinerary when you plan to explore the hills and valleys of Tuscany.
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Nestled atop a hill that overlooks hectares of vineyards in southern Tuscany, Montepulciano is just as charming as it is beautiful. The town, full of Medieval architecture and historic churches, is a terrific jumping-off point for exploring other smaller towns nearby, like Bagno Vignoni. Known as the home of the famed Vino Nobile di Montepulciano, you’ll have no trouble finding vineyards and underground wine cellars surrounding the town that produce this noble Italian wine. Pro tip: bring good walking shoes, and prepare for some steep climbs around town!
Situated in Val d’Orcia of southern Tuscany, the beautiful valley surroundings of the Pienza countryside are enough to make it worth a stop on your itinerary. But the small town’s appeal certainly doesn’t stop at its idyllic location—it was created by the humanist Enea Silvio Piccolomini, who set out to transform Pienza into the epitome of an ideal Renaissance city. Between the harmonious architecture and the travertine stone used for buildings, you’ll want to spend hours lingering among the town squares and historic monuments. Don’t forget to sample some of the famed Pecorino of Pienza!
Come to Volterra prepared to learn all about its fascinating Etruscan history (think 4th century), and stay here for the world-renowned local goods handmade from beautiful alabaster. You can spend your days wandering—essentially time traveling—through the impressive Etruscan and Roman remains, like walls, gate, an Acropolis and Roman theater, and then explore the quaint shops, restaurants, and surrounding farms.
Ah, Lucca. Considered one of the most-loved towns of Tuscany, this sweet village is situated in the region’s north, at the foot of the Apuan Alps. Just a thirty-minute drive from the coastal province Versilia (plan for a beach day!), Lucca is very accessible, and especially nice for those who want a break from climbing hills as it’s located on a plain at the base of the mountains. History buffs will rejoice upon seeing the ancient Roman amphitheater and the remains of churches and villas from the 6th century to the 12th.
Conveniently located almost smack-dab between Siena and Florence, San Gimignano is a UNESCO World Heritage Site, and home to ample Medieval architecture well worth a day of exploring. Make sure to take time to shop for local products, like saffron and the famous local wine, Vernaccia di San Gimignano. If you’re up for some outdoor adventure, we recommend taking a long day hike, following along the Wine Road of the Vernaccia di San Gimignano, to get some excellent views of the little city.
With a prime location between Tuscan hills and the Etruscan Coast, Suvereto is undeniably one of the prettiest towns in Italy, and home a fascinating Medieval history and a buzzing wine industry. Surrounded by forests and gently rolling hills, this is a particularly relaxing Tuscan town, and one that is deeply tied to the land, boasting local artisans that work with materials like cork, wood, and of course: wine. Part of the Wine Trail,
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