The Perfect Tuscany Road Trip

One balmy evening in Tuscany, my husband steered our rental car onto a rural road between clifftop Montepulciano and our farmstay for the night. The rugged hatchback rolled smoothly over narrow lanes bookended by rustic wooden fences. Pink clouds streaked across the sky. A summer breeze ruffled the tall grasses. As the Aperol-colored sun sank, we rolled the windows down and gaped at golden fields, stately cypress trees and Italian estates. I smiled and thought, “This. This is why I travel.”

More than anywhere else, travel in Tuscany feels like stepping into a sunlit postcard — only this visual treat is complete with the aroma of herbs, fresh cheese and the taste of a dozen vino della casas (wines of the day). It is holiday bliss. That’s probably why I’ve spent the last two summers road-tripping through the region.

If you also dream of driving through the rolling countryside of one of Italy’s most scenic regions, here are highlights from my Tuscany road trip to help inspire you.

Preparing for an Italy Road Trip

Before any international road trip, I get my documents in order. For Italy, that includes a passport and an International Driving Permit (IDP). U.S. citizens can travel in Italy for up to 90 days without a visa.

IDPs are valid for only one year, so I’ve gone through several. Fortunately, the process is painless. Simply take a valid state driver’s license to my local AAA office, pay a $20 fee and that’s it! I can now legally drive in dozens of countries. AAA members can obtain an IDP at any AAA Northeast branch; AAA is the only authorized provider in the U.S.

Once I have an IDP in hand, it’s time to book a rental car.

A Road Trip Through Tuscany

For such a small region — slightly larger than New Jersey — Tuscany offers a bounty of villages and vineyards to explore. It would be possible to drive through in a day, but the best way to see Tuscany is to take it slow. Drink in the views, stop for roadside photos whenever inspiration strikes and plan to see just one or two towns per day. The joy is in the journey, after all.

Most road trips through Tuscany begin and end in Florence. It’s also possible to start in Florence, explore Tuscany, and dip south into Umbria on the way to Rome. No matter where the trip begins and ends, these Tuscany icons and lesser-visited gems shouldn’t be missed.

San Gimignano

It wasn’t love at first sight between San Gimignano and me. On our first Tuscany road trip, we visited this small, 13th century walled town for just one afternoon. The parking lots outside the walls were clogged with tour buses. Piazza della Cisterna, the central square, swarmed with crowds slurping melting gelato under the brutal summer sun.

But I gave this classic a second chance. On our last trip, we spent two nights at La Cisterna, an inn inside the city walls. What a difference! In the mornings and evenings, San Gimignano is another world entirely. The village wakes up slowly. At night, wandering the maze of streets centered around medieval towers feels like stepping back in time.

Certaldo

While staying at an agriturismo — a working farm with rooms to rent — outside San Gimignano, we asked our host where she would drive for a nice dinner. Certaldo, she said immediately.

The first treat in Certaldo was the cable car running from the modern town center to the compact, walled village above. Once we got to the top, all that was left to do was meander quiet cobblestone streets toward our host’s favorite restaurant: Ristorante L’Antica Fonte. We dined on fresh pasta and crisp white wine under an eave of foliage that made the restaurant feel like an enchanted garden. Clear views of San Gimignano across the valley were the cherry on top.

Montepulciano

When it comes to panoramic views, Montepulciano is hard to beat. The quintessential Tuscan town rises steeply from the main road. From afar, it looks like a formidable fortress. As we drove closer, the weathered, chalk-colored walls reflected the afternoon sun, and the pretty dome of the Sanctuary of the Madonna di San Biagio came into view.

The gardens, views and charming streets filled with shops and restaurants were worth the steep walk up in town. And it’s impossible to visit Montepulciano without enjoying at least one meal. Montepulciano is known for its local red wine, vino nobile, which pairs perfectly with one of my favorite Tuscan treats: pecorino cheese.

Siena

Siena is no hamlet — it’s a full-fledged Italian city with a massive, ornate cathedral and a distinct fan-shaped central square that hosts the twice-annual Palio di Siena, a storied horse race marked by much pomp and circumstance.

Like many Tuscan towns, Siena has a massive pedestrian zone. Parking can be challenging. In both 2022 and 2023, we found an empty spot at “La Stazione” paid parking only after circling the block for several minutes. But Siena is worth the wait. Its grand walkable streets are the perfect place to get lost for hours. I recommend hopping from a sunny pizzeria lunch to afternoon aperitifs to a sumptuous supper at one of the city’s five Michelin-starred restaurants.

Monteriggioni

If Hollywood made a movie set of a Tuscan village, it would look like Monteriggiono. Too small to be considered a town, the so-called commune consists of little more than a square that extends into three parallel streets. A perfect ring of medieval walls surrounds the tiny community. Still, it’s worth a visit — perhaps even an overnight stay — to stroll the cobblestone streets, pop into a handful of curated boutiques, and light a candle inside the small church. My perfect evening in Monteriggioni would include dinner at Ristorante Le torri Monteriggioni, where service is fabulously attentive, and a nightcap at uber-stylish Pit Stop 17.

Pienza

Located in Tuscany’s golden Val d’Orcia region, Pienza was the birthplace of Pope Pius II and was purportedly renovated to be “the ideal Renaissance town” in his honor. Beautiful wooden doors punctuate Pienza’s charming stone walls. The buildings practically drip with flower blooms in spring and summer, and cafes are located strategically to invite diners to drink in the views. We’ve twice stayed outside the town property. I vow to book one of the pretty terraced Italian rooms inside Pienza’s enchanting walls for our next Tuscany road trip.

Plan your road trip through Italy with a AAA travel advisor today. Travel advisor services are included with your membership at no extra charge.

The Perfect Tuscany Road Trip

Preparing for an Italy Road Trip