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Andiamo! Italy’s Coolest Road Trips to Take Your Wheels

Beautiful happy tourist girl friends enjoying scenic view arms raised of Amalfi Coast on summer road trip adventure vacation in vintage van
Written by Suzy Guese

In a country of rolling countryside, dramatic coastal cliffs, towering mountains, and history around every bend in the road, Italy makes for the perfect road trip destination. From the northern mountains all the way down to Italy’s heel of Puglia, la dolce vita is alive and well, especially if you have your own wheels for exploration. And while you could just set out in your car rental without a plan or even a map and find jaw-dropping beauty in this country, these road trips around Italy will never leave you running on empty.

The Dolomites

Road trip in a white car in autumn through the Funes valley in Dolomites area in South Tyrol, Italy with the village of Sankt Magdalena in the background.

Take your wheels on up to northern Italy and you’ll discover almost another country. The Dolomites encompass a mountain range straddling the border between Italy and Austria, lending this area a decidedly more alpine, Germanic feel. You can find one of the best road trips to experience the Dolomites, those distinctive craggy gray peaks, by cruising the Grande Strada delle Dolomiti. Beginning in the village of Cortina d’Ampezzo, roughly 2 hours north of Venice, the road trip takes you over Falzarego Pass and Pordoi Pass, while ultimately winding up in the quaint town of Bolzano. That journey spans about 100 kilometers so you’ll want to allot time for stops and detours to roam through mountain settlements like Belluno, wildflower meadows, and lush valleys like the Val di Fassa.

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empty road and green hill in Tuscany, Italy

The Italy of imaginations is often that of Tuscany. You can begin exploring the region starting in Florence, heading on the SR 222 Strada Chiantigiana. The road takes you through the heart of Chianti, stopping in medieval towns along the way like Greve in Chianti, and of course, the area’s esteemed vineyards. Once you reach Siena, the fun doesn’t end. You can then road trip further south through the UNESCO approved Val d’Orcia. You really can’t go wrong anywhere in Tuscany, but this corner boasts those rolling green hills speckled with cypress trees and vineyards. Road trips in this area often begin in Siena, heading down Montalcino, home to the famous Brunello di Montalcino wine. In between wine tastings, the Val d’Orcia leaves plenty of Renaissance towns to explore too, especially the idealized Pienza.

The Amalfi Coast

Amalfi Coast, Italy

Arguably Italy’s most famous stretch of coastline, the Amalfi Coast, just south of Naples, presents a dramatic coastal road along the Tyrrhenian Sea. The SS163 Amalfitana runs from Vietri Sul Mare towards Sorrento, covering some 50 kilometers of hairpin turns, nail biting moments, and colorful cliff-clinging towns. This stretch of coastline has even warranted the approval of UNESCO, landing on its World Heritage list. While the road can be slightly terrifying, especially if you encounter a tour bus, somehow, everyone gets by and the scenery makes the hair-raising journey worth the trouble. You’ll want to plan time for plenty of stops along the way, especially in the chic town of Positano and the up-in-the-clouds, picturesque community of Ravello.


Italian vacation - Otranto in Puglia

The heel of Italy, known as the Puglia region, does not boast Italy’s most well-traveled roads. Puglia is still a bit off the tourist radar. You can hug the coastline with the Adriatic Sea, stopping in big cities like Lecce and Bari, or go the more small town route, discovering the whitewashed villages of Locorotondo, Monopoli, and Polignano a Mare. No matter which route you travel, you’ll want to be sure you make detours for two Puglia stunners, Castel de Monte, a rare octogonal 13th-century wonder; and the village of Alberobello, known for its conical houses, the trulli. If you have the time, you can even make your way down to the very tip of Italy’s stiletto at Punta Ristola.

What’s your favorite Italian road trip? Share with us below!


About the author

Suzy Guese

Suzy Guese is a travel writer from Denver, Colorado. She caught the travel bug after taking her very first flight at just three months old—she was headed for Disney World—and has been a total travel junkie ever since. From family car trips across North America to stints abroad in Europe, Suzy travels the globe with her redheaded temperament in search of sarcasm, stories, and travel tips to share with anyone willing to listen. She blogs about her travels at