And we’re off on our Tuscany roadtrip! After three days immersed in Renaissance Florence, we embarked on a journey through Tuscany in our rented – very little – Fiat.


We picked up our cute little vehicle at Florence’s Peretola Airport and, after a few circles around the parking lot to familiarize myself with driving a manual again, we headed south on the autostrada into the heart of Tuscany.

Though the four-lane autostrada could actually take us all the way to Siena, we preferred the more scenic route. So, after a few wrong turns, we finally found the SS2, or La Cassia, and motored deep into Tuscany’s verdant patchwork. This two-lane country road was narrow, undulating and twisty, a test for my rudimentary manual-driving skills. But the views were certainly worth the hassle.


Stunning Tuscan vistas.

Outside of the city’s confines, the air smelled of lavender, sunlight danced through swaying cypress trees and ripe vineyards blanketed the hills as far as the eye could see. Villas sat proudly on their lofty perches, each more lavish and alluring than the previous. Rose vines and clematis climbed stone walls and chickens ran free through backyards. It was an idyllic setting.

Our goal was to reach Pienza by early evening. Therefore, we had the entire day to thoroughly explore the region and drive slowly with the windows down. We paused to wander through gorgeous hill towns, resplendent with burgeoning flowers, honey-hued architecture and cobbled lanes. Market stalls abundant with succulent grapes, crusty bread and freshly made pastas spilled into the streets, and provided our flavorsome lunch of fresh baguettes, mozzarella and sliced tomatoes .


Tuscany’s market stalls!

The truth about driving in Tuscany: While taking a Tuscany roadtrip and being the masters of our own itinerary was exciting, driving – and navigating – in Italy is quite possibly one of the most disastrous and frustrating tasks one can subject themselves to. Speed traps, poorly marked signs, rude drivers, the infamous “ZTL” zones and congested streets can make anyone lose their temper and get discouraged.

I also made the mistake of not renting a GPS when I booked our car online. I thought our huge, multi-page map would be just fine to help us navigate through Tuscany. It wasn’t. At all. The problem was that the roads changed names and numbers at almost every turn, and the road signs never actually matched the map’s record. On more than one occasion, we found ourselves completely lost and confused, and we made many u-turns punctuated with many more light-hearted arguments. Luckily, whenever we stopped to ask questions (which we did quite often), the locals were quick to help and point us in the right direction.


Which road?

Aside from the frustrations of driving, our four days with the Fiat led us through many of Tuscany’s best towns. From the thoroughly medieval city of Siena and it’s sprawling Palazzo del Campo to quieter Buonconvento where locals relaxed in leafy gardens, we explored some of Italy’s true gems, tasted the region’s iconic wines and stuffed ourselves with pasta, pizza and pastries; all while cruising under Tuscan blue skies.


Siena’s sprawling Piazza del Campo

Our accommodation was perfect! We stayed near Pienza in an authentic Tuscan villa that I booked on an Agriturismo site. Breakfast was included, and the villa featured hammocks, cozy beds and splendid Tuscan views of farmland and vineyards. The town center of Pienza was a short drive away, and we spent many the late afternoon strolling its streets and observing local life. Men gathered to play card games and chat; the women gossiped on park benches; and the town’s children rolled past on bicycles or chased pets up and down the cobbled lanes.


During the following three days, we continued our Tuscany roadtrip and passed through the town’s of Montepulciano, Volterra, Lucca and Pisa. Though all were equally lovely and charming, Montepulciano certainly wins the prize of “Favorite Tuscan Town.” Mom and I spent an entire morning wandering through its medieval streets and sampling goodies from its wine cellars and cheese shops. Plus, as Montepulciano sits high on a hill, views like this waited from the lookouts of its fortressed walls. It was a heavenly, harmonious locale.


I can understand why Tuscany is such a beloved spot for many: It simply feeds the soul. The breezes felt cooler on the skin; the skies were just a bit larger and a bit bluer; and the pace of life more left more languid and serene. Tuscany is a region to return to again and again.