A Taste of Tuscany: Visiting Tuscany and Chianti on a Day Trip from Florence

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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.

Sunset in Tuscany

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 Amanda (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.

Siena Cathedral

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.

Siena Cathedral
Siena Cathedral

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.

Siena Piazza del Campo
Siena's Piazza del Campo
Siena street
Siena street

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.

Chianti wine tasting
Chianti wine tasting
Chianti wine tasting
Chianti wine tasting

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.

Tuscan farmhouse dinner
Tuscan farmhouse dinner

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.

Chianti wine region

If you go…

I did my tour with a company called Italy on a Budget Tours, 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:

Would YOU like to explore Tuscany this way?


"It's a dangerous business, going out your door. You step onto the road, and, if you don't keep your feet, there's no telling where you might get swept off to." - JRR Tolkien

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24 Comments on “A Taste of Tuscany: Visiting Tuscany and Chianti on a Day Trip from Florence

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  1. Your picture brought back great memories, thank you for sharing them! We actually took a tour with the same company, it was loads of fun (and even more wine ๐Ÿ˜‰ )!

      It was such a great day out in Tuscany!

    […] for example, booked the best walking tour I’ve ever been on in Berlin, took a day trip out into the Tuscan countryside from Florence, went rafting in Cesky Krumlov, and took a “Sound of Music” tour in Salzburg — […]

    […] complete without wine tasting. This tasting table was set up at a small, family-owned winery in the Chianti wine region, and we tasted wine and had dinner as the sun went down over the vineyards. Blissful doesn’t […]

    What a great surprise to find this post about one of our tour! We are glad you enjoyed the day in the Tuscan countryside and the photos look great. Anyone willing to experience, learn, taste and see what Italy and the territory has to offer in a fun environment together with our young, lively and knowledgeable team is always welcome. Thanks for supporting a local business ๐Ÿ™‚

      Of course! I really enjoyed the tour, and am happy to help promote it! Like you said, support local businesses!

    definitely a good way to see a bit of the beautiful region! great pics

      All the great things you hear about the Tuscan countryside are absolutely true! Glad you liked the photos.

    Amazing pictures! When we visited Florence and the area we used Walks of Italy for some tours and they were also fabulous. We look forward to looking into this tour when we get back to Tuscany next year. It would be great to explore the region more.

      I also took a few tours with Walks of Italy this summer and agree that they are great! But I’m always up for trying new companies, and this one was a good choice, too. Plus, I love that it’s locally-run! Definitely look into it next year.

    That second photo of the Siena Cathedral is absolutely beautiful. I loved this post and will use it to help plan my trip to Italy in the spring! Thanks for sharing.

    Happy travels ๐Ÿ™‚

      I’m glad you found it useful, Lauren! You’ll have to let me know if you end up at any of these places yourself!

    That sounds like a great price ๐Ÿ™‚ I must save that somewhere as I’d love to do this when I eventually go to Italy. Was this something separate you did from Busabout or was something they recommend?

      It was definitely worth the price! Bookmark it for sure.

      The tour was recommended by Busabout, but operates completely separately. I did quite a few Busabout-recommended tours this summer all across Europe, and they were all really great!

    How great a day is it? I did the tour a little while ago and loved it. Your photos made me experience it all over again ๐Ÿ™‚ There’s still more of Tuscany that I want to see, though – San Gimignano being at the top of the list!

      SUCH a good tour! I’m really glad Busabout recommends this company.

      And I’m with you on San Gimignano! I really want to go there, too.

    I’m jealous about your stop in Monteriggioni. I never made it there, but I explored the streets of Siena thoroughly during a day trip from Florence. I entered the Duomo and the other buildings connected to it. Very interesting!

      I sadly didn’t go inside the Duomo in Siena. I planned to and even got in line to buy a ticket. But, even though the brochure I had in my hand said that the Duomo was 7 Euro to enter, the guy at the ticket counter tried to charge me almost double! I didn’t want to see it THAT bad, especially since I’d just come from seeing St. Peter’s for FREE in Rome.

    Balsamic vinegar on ice cream… hmmm…

    The photographs are gorgeous. Especially the colors of the homes against the sky… that’s the kind of brown color scheme designers dream about. Beautiful!

      It doesn’t sound good – but the flavors actually worked well together!

      And thanks for the compliment on the photos! Though, to be honest, it’s easy to take great pictures in Italy.

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