Europe Italy

A Tuscan Road Trip Itinerary (Part 1): Medieval Siena

May 3, 2016

When people talk about the rolling hills of Tuscany, they aren’t exaggerating. What you will see on a road trip through Tuscany is literally a scene out of a postcard (if not better) with gorgeous medieval towns and beautiful vineyards. If you’re visiting in the summer and have more days on hand, you should definitely consider staying in Tuscany for a few days. But if you’re tight on time, a day trip through the region is doable too.

I visited Italy in February, so it didn’t make sense to do more than a day trip through the Tuscan countryside, since the winter meant a lot of restaurants and hotels were closed. However, if you are planning to stay for several days, you can simply extend my itinerary by spending more time in each place. Here’s a rundown of my road trip through Tuscany for a day, and all the information you’ll need to plan your trip too 🙂

Part 1 covers basic information about the Tuscan region, how to get around, and why you should visit Siena. In Part 2, I’ll provide tips on how to choose a vineyard from the numerous options available, and share stories from my visit to a vineyard!

Tuscany overview:

The two most important and famous wine-producing regions in Tuscany are Chianti (in the area between Florence and Siena), and Val D’Orcia (in the area between Siena and Monte Argentario). Val D’Orcia is the most beautiful, and the one you’ve seen photographed in pictures of Tuscany – it’s a UNESCO World Heritage Site!

You can certainly get to some of the towns in the Tuscan region through public transport (such as Siena and Pienza), but to really enjoy the countryside, and visit smaller villages, you’re better off renting a car. This gives you the flexibility to stop wherever you’d like. After all, the beauty of a trip to Tuscany is more in the journey than the destination itself!

If you do plan to stay overnight in the Tuscan countryside, choose Pienza or Montalcino – beautiful quaint towns, with lots of accommodation and food options.

When to visit:

While summer is a popular season for obvious reasons, I was pleasantly surprised with how gorgeous the region is even during the winter – sure, there are no grapes in the vineyards (harvest season being November), but the rolling hills and trees are still (surprisingly) lush green! So don’t shy away from visiting in the winter as well.

Hills of Tuscany road trip

Didn’t I get lucky with weather in February?

The Chianti Region – Drive from Florence to Siena:

We left Florence around 9am after breakfast, and were in Siena by 10am since we chose to drive along the highway. If you’re looking for a more scenic drive, take the SR222 – it only takes about half an hour more, but you’ll pass through the gorgeous countryside!

Driving directions Florence to Siena

Take the SR222 highlighted in blue for a scenic drive. Take the highway marked in orange for a quicker drive.

Tuscany countryside views

Views like this while you’re driving!

Siena is a beautiful medieval town, very popular with locals for weekend getaways during the summer. Since we visited on a weekday in the middle of the winter, it was pretty isolated but there was still something so charming about it. There were hardly any tourists on this winter morning, and the locals were just going about their regular business. Moments like these allow you to experience travel for what it really is, away from the chaos of tourist-filled sights and attractions!

If you arrive by car, you’ll need to park in one of the parking garages outside the city center, since no vehicles are allowed inside. Siena is set on a hill, and the walk to the city center is pretty steep, so be prepared to walk a lot. 


The entire town is filled with brick buildings and green windows

Green Windows Siena Streets



The Duomo in the central square is worth checking out – one of the most gorgeous cathedrals I’ve seen on the inside.

Duomo in Siena

Siena Duomo on the inside

Interiors of Siena Duomo

Stainglass and bell in cathedral Siena

Stunning interiors of the Duomo

Since the town was pretty isolated, and a lot of restaurants and cafés were shut due to the winter, we only wandered around Siena for a couple of hours, before making our way further south into the Val D’Orcia region. I’ll be posting the second half of my road trip (from Siena to the Tuscan vineyards) in part 2 of this series, along with information on how to select a vineyard to visit.

Have you been to Tuscany? What are some of your favorite towns? 🙂