Chances are, if you're a woman, you've fantasized about this scene: a country terrace, a glass of wine, and the sun setting over the hills of Tuscany. Hell, I'll bet men even fantasize about this.
Because it's a damn pretty thing to daydream about.
And when I finally got to experience it for myself? Well, let's just say that it was pretty surreal.
My foray into Tuscany beyond the city of Florence began on a hot and sunny August afternoon. As many of my forays do.
I was in an equally hot and sunny van with a handful of (mostly) Australian backpackers, laughing out the open window as we all chose Italian names for the day. I remained Akatuki (said with elongated “A”s in a sexy accent), while others settled on more outrageous names. One girl, for example, was obsessed with the name “Giuseppe,” and called herself some made-up female version of it for most of the afternoon.
As we made our way out of Florence and into the Tuscan countryside, my guide (and also owner of the company) Irene began telling us about the region – she covered everything from the history to the food to the language to what the men are like there.
Irene was born and raised in Tuscany and worked as a tour guide all across Europe before deciding to launch her own company in the country she knows best. As she cracked jokes with us and asked us all about our travels, I knew that it was going to be a fun afternoon.
Tuscany is known for quite a few things: its history, its art, its landscapes, and of course its food and wine. And I was able to get a taste of all of the above in one day.
Highlights from a Tuscany day trip
Our first stop was in Monteriggioni, a medieval Tuscan town with its fortress-like walls still intact.
Once we arrived at the village, Irene set us loose with a gelato suggestion and about 45 minutes to wander around. It was more than enough time, considering that you can walk from one end of the town to the other in about 5 minutes.
I paid a couple of Euros to climb two sections of the medieval walls, which date back to the 1200s and offer up some nice views out over the Tuscan countryside.
From Monteriggioni, we continued on to Siena – the historical rival of Florence. The two cities were frequently at war well into the 1500s, and the stories of this rivalry are interesting to hear.
For example, the Siena Cathedral (the Duomo) is so grand because it was trying to out-cathedral the Duomo in Florence; Siena wanted to make it the largest cathedral in the world.
In Siena, Irene led us all through the streets to the Piazza del Campo, told us where the main sites were located, and gave us a little over an hour to explore the city on our own.
Wine tasting in Chianti
After Siena, we began a twisting drive up into the Chianti wine region. We stopped at a local winery, where a table was set for us to try some wines and cheese, some extra virgin olive oil, and a special treat – truffle oil.
“Italian George Clooney” (as we dubbed our host) finished the tasting with balsamic vinegar drizzled over vanilla ice cream — it was tastier than I expected!
Once pinks and purples began to creep into the sky, we took our leave and headed to dinner.
Dinner at a Tuscan farmhouse
Our last stop of the evening was at a traditional Tuscan farmhouse, where we were greeted with huge smiles and what seemed like never-ending portions of food. There was homemade bruschetta, meats and cheeses, and overflowing plates of pasta.
Our group was treated more like family rather than a group of tourists, which is really what this whole experience is about.
In just one day, it's impossible to really see or experience an entire region — especially one as diverse as Tuscany. But I still feel like I managed to get a nice little taste.
Enough of a taste to make me hungry for more.
If you go…
I did my tour with a company called , which specializes in tours for the 18-30 crowd. The exact tour I did is no longer offered, but they still have several similar tours that combine wine tasting with sightseeing in Tuscany/Chianti. Their tours are also very budget-friendly!
For other similar tour options, consider:
- (super highly rated)
- (with lunch and wine tasting)
Would YOU like to explore Tuscany this way?