Italy's Tuscan Countryside Thrives On This Road Trip Route Through Hills, Medieval Cities, And Vineyards

There's nothing like driving along cypress-lined roads through the Tuscan countryside to kick off a dreamy summer vacation in Italy. In fact, travel expert Rick Steves strongly recommends renting a car when exploring Tuscany. A spectacular route you shouldn't miss out on is the two-day road trip starting in Florence and wrapping up in Orvieto, going from Tuscany to Umbria in a whirlwind of scenic vistas.

Florence, of course, is world famous for the dazzling red cupola of the Duomo dominating the skyline, its cobbled piazzas, and breathtaking medieval architecture. On the other hand, Orvieto, while more underrated, is equally magnificent, boasting its own Duomo in the Gothic style. Along the way, stop at Greve in Chianti to try the region's mouthwatering steaks and fragrant wines; then head over to Siena, another stunning medieval town. Stay overnight in Siena to soak up the historic atmosphere, then drive to Montalcino for a taste of the famous Brunello wine while basking in the inspiring vistas of the Val d'Orcia, a sweeping valley of undulating hills broken by ancient castles and olive groves. From there, head to Pienza and Montepulciano — two fantastic hilltop towns — before slowing down as you reach your journey's end in Orvieto.

If you're feeling ambitious, you could even add more days to the itinerary. This would give you ample time to make detours along the way at local restaurants for hearty bites of pasta and at sprawling vineyards, where you can sip delicious Chianti. As you blaze through these charming Tuscan hill towns, be sure to look out for the words "alla toscana" and "alla fiorentina" on menus when deciding on what to eat (meaning cooked in the Tuscan or Florentine style), as recommended by Rick Steves on how to dine like a local in Italy.

While in Florence, don't forget to check out some of the iconic landmarks before you hit the road, like the stunning Basilica di Santa Croce, or the Medici family's majestic Palazzo Pitti. Then, set off southwards to Greve in Chianti (just 45 minutes away) and stop at the Enoteca Falorni in the town's historic center — or rather, beneath it. Located in an underground cellar, Enoteca Falorni offers over 100 wines for tasting along with a range of cheeses, and it has excellent reviews on TripAdvisor.

There's also the Montecalvi estate just outside Greve, a romantic vineyard with a stunning villa where wine has been in production since the 1400s. Wine tastings from the estate's sunny terrace give you fantastic views of the sweeping Tuscan hills. Then, it's roughly an hour's drive further south to Siena, concluding day one. Highlights here include the Piazza del Campo, the iconic semicircular public square fringed with cozy cafés, along with the Palazzo Pubblico, the Gothic town hall with its crenellated tower.

Arriving in Montalcino on day two, stop by the Fortezza di Montalcino, a medieval stronghold with its own dedicated wine shop. Drink in the stunning Val d'Orcia hills from the Fortezza's ramparts before stocking up on a few bottles of Brunello from the Enoteca la Fortezza downstairs. Next is a 30-minute drive to Pienza, a Renaissance village famed for cheese. Don't miss Podere Il Casale, an organic farm and restaurant producing the cheese known as pecorino, the town's specialty. From here, Montepulciano is another 20 minutes away, where you can climb the medieval Palazzo Comunale for breathtaking Val d'Orcia views. The final stop, Orvieto, is about an hour's drive from Montepulciano, where you can toast a road trip well done with a glass of Orvieto Classico at the Enoteca al Duomo, steps away from Orvieto's stunning cathedral.

Stretch the two-day itinerary further with a few worthwhile detours along the way. After leaving Greve in Chianti, you could veer off to Monteriggioni while on your way to Siena. Built on a hill and encircled by a medieval stone wall with fortified turrets, Monteriggioni has been called "the gateway to the Middle Ages" for its historic architecture and atmosphere. Only a 45-minute drive from Greve in Chianti, you could choose to spend the night in Monteriggioni, as there are several hotel options, or you could just do some quick sightseeing before driving another 25 minutes to Siena.

You'll have plenty of accommodation options while in Siena. Though a little pricey at more than $350 per night in high season for a double room, staying at the Grand Hotel Continental Siena will leave you feeling like a pampered Tuscan duke. Just steps away from the Piazza del Campo, guest rooms here are stunningly frescoed and furnished with elegant accents, like exquisite chandeliers. The hotel also boasts a lounge where you can enjoy aperitifs along with a gourmet restaurant serving delicious Tuscan cuisine. A more affordable option (around $100 per night for a double in high season) is the Hotel Italia, still conveniently near the historic center and with charmingly rustic guest rooms.

Another detour from Montalcino: Instead of heading directly to Pienza and Montepulciano, drive south from Montalcino for about 12 minutes to make a stop at the Abbazia di Sant'Antimo. This mesmerizing Romanesque monastery dates back to the 12th century and is tucked in a serene valley dotted with vineyards. Grab unique souvenirs from the monastic pharmacy, which offers a range of medicinal remedies and all-natural body care products plus fruit jams and herbal teas made according to medieval recipes. Whether you finish this road trip in two days or extend it with a few outstanding detours, this drive through Tuscany is sure to be the adventure of a lifetime.