Experiencing the Best of Tuscany (in One Day!)

November 20, 2014 Updated: November 20, 2014

Ever since I had decided I would go to Europe, people began asking me if I would make it to Tuscany. It seemed like everyone I talked to raved about this region, calling it their favorite in all of Italy, even random strangers I talked to while in a queue in Hong Kong.

I pulled out my phone to pull up pictures of this area, because I’ll be honest, I had never seen Under the Tuscan Sun and really knew nothing about this part of Italy.

It was those photos that convinced me to go.

Counting the days available in our itinerary, it just didn’t seem feasible for this trip. I tried my hardest to rearrange what I could and in the end, I decided to cut days off of our time in Rome in order to squeeze in the Tuscan countryside.

Was it worth it? Yes, oh very much so!

Was it rushed? Uh, yes, very much so!

Luckily, with a little help of our friends at Walkabout Florence, we were able to see the highlights of Tuscany in only one day, which was just enough to make us want to come back for more.


We began our day by driving out to Siena. This was actually the area that Mr. Hong Kong Line Man raved about the most– and I can see why.


(Beth Williams, BesuDesu Abroad)
(Beth Williams, BesuDesu Abroad)


I adored the colors of this city with its yellow-ochre buildings, orange rooftops and green shutters. As our guide showed us around, she explained about the 17 different contrade, or districts, that make up Siena. Each represented by a different creature, some seemed so powerful and cool like the dragon, the unicorn or the eagle.

And then there were those that had me giggling and almost feeling sorry for those that were represented by such lousy creatures. I wondered how they had drawn the short stick to get stuck with the snail or the caterpillar.

Regardless, I loved how the lamps on the buildings would change as you entered each distinct district to match those of their mascot. I began running around trying to take photos of as many as possible, feeling like I was trying to catch Pokemon or something.


(Beth Williams, BesuDesu Abroad)
(Beth Williams, BesuDesu Abroad)


I immediately became sidetracked however upon sight of the Piazza del Campo. Home of the famous Palio horserace, this seashell-shaped square is said to be one of the most beautiful in all of Europe. I’ll agree. I now know why so many of you have e-mailed me telling me you got married there!

After soaking up some sun in the square, we continued onward to the Siena Duomo. Now I know people go on and on about Florence having the most beautiful duomo, which, from the outside, yes, it does. Honestly from the inside though, I thought the colors and symmetry of Siena’s duomo were far superior.

From the scenes portrayed on the floors, to its giant dome, to its amazing library, the whole thing was gorgeous.

In the end I think I drained most of our time in there, because before we knew it, it was already time to be taken to our next destination…

Fattoria Poggio Alloro

Out in the true hills of Tuscany, this little gem was the highlight of my mom’s day. An organic, family-run farm and winery, Fattoria Poggio Alloro was the perfect stop for lunch.


(Beth Williams, BesuDesu Abroad)
(Beth Williams, BesuDesu Abroad)


The workers kindly gave us a tour of the vineyards and olive groves, before escorting us to the most beautiful pavilion where we’d have lunch. Can you believe these views??

This is seriously one of the most beautiful places I have ever eaten!

And most importantly, not only were the views amazing, but the food was too. We were served a fresh, multi-course meal and with each dish they had paired a different Italian wine for us to sample.


(Beth Williams, BesuDesu Abroad)
(Beth Williams, BesuDesu Abroad)


In the end we had sampled four different wines including Chianti and Vernaccia. For dessert we got to try another specialty, which was a Tuscan biscotti that you dip in Vin Santo. This Italian dessert wine almost had a sherry taste to it. While it was strong, it was also the perfect treat for a hot summer afternoon.

San Gimignano

Just a few short minutes drive from our lunch spot and we were in San Gimignano. And when I say short, I mean really short, like, ugh-why-did-I-drink-so-much-wine-at-lunch-I-thought-we-had-a-longer-bus-ride short.


(Beth Williams, BesuDesu Abroad)
(Beth Williams, BesuDesu Abroad)


Luckily, our guide explained everything we needed to know in advance and we let loose to explore on our own. I think they must’ve learned through trial and error, that after liquoring people up, it’s probably best to let them explore on their own rather than trying to keep everyone corralled on an organized walk.

As one of Italy’s most enchanting medieval hilltop towns, San Gimignano was lovely. We stopped in cute boutiques, wandered through its picturesque streets and saw its famous towers, although we didn’t climb them. Instead we spent our time climbing up to Rocca di Montestaffoli, which was once a castle. Now it’s only ruins and a park, but you can climb one of the ancient turrets to get an amazing view of the walled city and surrounding countryside.

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Copyright © 2014 by BesuDesu Abroad. This article was written by Beth Williams and originally published on BesuDesu Abroad

*Image of landscape in Tuscany via Shutterstock