Looking back on our Italy trip Tuscany is the main place we wish we could have spent more time. While we wish we could go back to every location we visited because of how much we loved what we got to do, we look back on Tuscany and wish we had more time because of the amount of things we didn’t get to do during out three days in this massive and beautiful part of the country. All this aside, we still did have an incredible time, and this post will outline how we spent the little amount of time we had to explore this region.
Our first stop on this leg of the trip was in Florence, which was our gateway into Tuscany. We made it to the city around midday and spent a few hours walking around and taking in the sights. We came on a Monday and it’s important to note that many if not all museums are closed on Mondays, so be sure to plan accordingly if you had your heart set on going to see any of the major art collections this city is home to. As it was, we only had a few hours to explore so walking around a museum on this particular trip was not in the cards. We strolled from the main train station south, and ended up having lunch at Trattoria ZaZa. We made a reservation in advance via their website which was very simple. Lunch here was great, I had a traditional boar tagliatelle, and M opted for a pizza. Both were incredible. We also had some panzerotti with parma ham and stracchino which were delicious!



After lunch we made our way to a couple souvenir shops I wanted to visit (we always collect some artwork to bring home on our trips), and then headed towards the famous Duomo. We didn’t have enough time to visit the famous dome, but the view from the outside is magnificent. We kept walking towards the river bank and the famous Ponte Vecchio to take in the stunning view of the city. We then stopped by a little cafe for a pick-me-up before heading to retrieve our luggage and rental car!


We rented a car through Sixt (located in the main train station) and somehow made it out of the crazy commuter traffic and to our hotel in the Tuscan countryside. We stayed in a resort town called Castelfalfi, which was our home base for the next two days of exploring.


The next morning we woke up around 8am to drive over to the town of Siena. Before arriving I scoped out a parking garage (parking can be kind of a nightmare in these Tuscan towns), and we headed up a few escalators and some hills into this charming town. Our first stop was the cathedral. We managed to get some tickets and spent about an hour walking around inside. We then did a quick stroll around the rest of the town before heading to our main activity for the day.




Leaving Siena, we drove about an hour south to Castiglion del Bosco, a winery owned by the Ferragamo family. This winery is located up on the hills and while the ride up is a bit bumpy, it is definitely worth it. We were treated to a little tour of their winery and taught about their processes before going to do some tastings. We are not huge wine drinkers (although M has picked up a taste for Italian wines since coming back from this trip) but we knew we wanted to try some of the local specialties. Tuscany is known for their reds, and Val d’Orcia is specifically known for their Brunellos, made from San Genovese grapes. This wine is highly regulated and has 40 different rules that need to be followed in order for the wine maker to be able to call it by this name.



We had an excellent tasting here, and our guide even brought us some special wines to try that weren’t on our tasting card after expressing interest. We came home with a couple bottles, as well as some olive oil and honey. I would highly recommend this winery to anyone who is in the area. The experience was lovely and we felt so well looked after.

The next day we headed to a winery called Tenuta Torciano. This winery was a bit closer to our home base and is where we arranged to have a truffle hunt and cooking class. This was so much fun as we got to interact with a local who had so much knowledge about the truffle growing and foraging process, and he had two super cute pups who demonstrated searching for the truffles! The actual truffle hunt took place in a grove owned by the winery where they plant special trees which are inoculated with truffle spores and then produce truffles for the winery to use and sell. The winery also provided a translator who was really kind and told us all about the winery which was owned by her family.

After our hunt we returned to the winery with some of our truffles and we had a cooking class. This experience was so much fun and we were led by an Italian chef through a three course meal with an appetizer, main, and dessert. We were then led to their tasting room where a sommelier guided us through a tasting of the wineries offerings (which we didn’t actually know was part of this experience) and got to enjoy the meal we had prepared for ourselves.
Our plans for after the truffle hunt and class were to go explore some of the small neighboring towns, however, as I mentioned before, parking in these towns is a bit of a nightmare so after a bit of driving around in circles around Montepulciano and Volterra we tucked our tails and headed back to our hotel.
This was a major lesson for this trip, to just slow down and enjoy lingering in spaces a little longer. I would say that you need about a day to properly explore each town, and while things look close together on a map it doesn’t necessarily mean you can visit everything all in one day.
Here is a cost breakdown of this leg of the trip:
Day 1 | |
Hotel (for 3 nights) | $1780 |
Rental Car (for 3 days) | $570 |
Day 2 | |
Siena Cathedral | ~$30 (for 2) |
Winery Tour (Catiglion del Bosco) | $74 (for 2) |
Day 3 | |
Truffle Hunt & Cooking Class (Tenuta Torciano) | $485 (for 2) |
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