Wineries. Quaint medieval towns. Epic Views. Nature. There is not quite a better way to unwind and soak in life.

Frankly, road tripping through Tuscany has been one of my favorite parts of my travels thus far. It’s such a bonding experience for couples, friends, or in my case, families. It allows you to set your own pace and experience wine country at your leisure.


I began my road trip from Florence (a city deserving of a whole blog post to itself) which is actually already in the Tuscan province. It’s the best place to start because it’s easily accessible from all other parts of Italy (many trains running through daily!) and has plenty of shops to pick up supplies for your trip.

First thing’s first when planning a road trip: car rental!

Car Rental

I booked online through Hertz which had some weekend rental deals but are generally cheaper if you book a week rather than just 2 or 3 days. There are a few other rental companies all in the vicinity of each other in Florence, so just walking in and asking around shouldn’t be a problem.

On to the fun part – the Fiat 500. To put it bluntly, this car was my favorite part of the road trip. I was dead-set on driving a Fiat, whether it was a 500 or other. Now for the road trip WE took, it suited our needs but it’s debatable how well it actually handled the routes we took. We took a few wrong turns and ended up going up and down a few steep gravel paths, which this little car seemed to struggle with. My sister drove and claimed (following a few anxiety attacks) it was not the nicest to drive up hills, but handled turns very well. I thought the Fiat was perfect as long as you stay on “main” paved roads. It fit 2 people plus our bags with room to spare and was the perfect size for all the narrow roads inside and outside cities. I give it a 9 out of 10 with the only extra suggestion of getting a convertible 🙂

Related: Necessities for a Car-Rental Road Trip


Driving Routes (from Florence)

I highly recommend doing day trips to surrounding cities and wineries but remaining at the Agrihotel Il Palagetto in Volterra.

-SR222 – A picturesque, scenic route from Florence through Chianti to Siena. No tolls, a bit curvy, and a plenty of little towns and wineries along the way.

-When making your way around/through Volterra, stick to the SR68, SR439, and the SP15 (road to the hotel). Beware of roads that seem to be “main” roads on your GPS/phone, because they aren’t and you’ll suffer a few panic attacks trying to dodge oncoming cars on a gravely, narrow cliff.DSC_0375

Where to stay

Agrihotel Il Palagetto, Volterra, Tuscany : We stayed in a hostel the first night and this exquisite hotel the second. My first piece of advice would be to stay in this hotel for the entire duration of your road trip. Perched on a hill with 360degree views of the rolling hills of Tuscany, sunrise/sunset, and the North side of Volterra, this hotel is where it’s at. In addition to all the rooms being spacious and having great views, the hotel provides an infinite pool, hammock, restaurant, bar, and wifi (which unfortunately did not work at the time). It’s perfect for couples, small groups, and relaxing – so I don’t recommend going solo unless you’re craving some alone time. The staff is very helpful, the amenities are excellent, and the price (roughly $45 a night) seals the deal.


Wineries & Sights

When choosing the wineries you’d like to visit. Make sure you do a bit of research first. Most wineries require a reservation if you’d like to do a tasting, and even then, you may have to pay. If intense wine tasting is high on your list, I’d suggest checking out a possible day tour so you can relax while being chauffeured through regions. We opted for free and easy, and because we did not have a designated driver, we only fit one actual tasting/tour into our schedule. My review of it follows:

Fontodi Winery : One of the larger producing wineries in the region of Chianti. I’m torn with reviewing this winery because since we were only able to fit in one, it’s hard to compare the full experience to others. So I’m naturally inclined to compare with South African and U.S. winery experiences – and unfortunately I have to say the visit was sub-par. To start, it’s signage is poor (a small wooden plank facing the opposite direction from where you arrive on the main road) and, though we had a GPS, still took us roughly an hour and half to find. We were relieved and still positive upon arriving – however, it was clear they weren’t fussed about catering to guests. I love rustic and homey places, but for travelers to come all that way, you’d think they’d have a few chairs to relax outside. The wine tasting was free (can’t complain there) and they had such potential with what great location they had. It’s simply a place to produce wine, taste a few, buy a couple bottles, and head out.


Volterra : One of the bigger “small” towns in Tuscany, Volterra is a great stop along your route. With plenty of wine bars, cafes, shops, and even a medieval torture museum, theres just enough here for a half day.

Others : We stayed a night at a cozy hostel in Castellina de Chianti – a very tiny town which seemed to be home to mostly retirees – and stopped for directions in Greve-in-Chianti. I would have loved to have made it to Siena but with getting a bit lost, we just didn’t have the time. I would absolutely suggest just driving around and stopping anywhere that peaks your interest – you’ll have a great experience and view, even if you get a little lost!


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