The way this trip came to be is a fun one. While on the road leading tours, my boyfriend and I were anxious to plan a vacation to follow our long work season. He had spent all summer in Alaska and I was still working down in the Lower 48. We decided to both pick 5 destinations which we’d like to visit for a couple weeks. Whichever one we matched on, we’d head to in late-September.
The reason for a visit to Italy was born! We narrowed it down to a few cities and incorporated a road trip through Tuscany too.
Of our 16 days in Italy, the highlight for me was renting a car and driving through the Italian countryside. Interestingly when researching the trip, all I read online were forums advising people to not rent cars in Italy and just take the train. No! I knew we wanted the freedom of a car. We went with it anyway, and I have no regrets.
From rolling hills, to wandering through medieval towns, our road trip was a perfect 5 days of bliss. Here’s how you can do the same:
Tip 1: Consider adding Umbria to your plans.
After a hefty amount of research and a handful of Rick Steve’s podcasts, I found that maybe the trip I actually desired was one through Umbria, a region right next to Tuscany but less well-known. It still had rolling hills and medieval towns like Tuscany, but was a little further off the tourist path. Now while you could definitely spend a week or more just exploring Tuscany itself, I’m glad we got a taste of both.
Actually, some of my favorite stops were all in Umbria! The food was heavenly and the towns were a fairy tale. On this road trip we also drove through Lazio & Viterbo, two other provinces that were just as fascinating and beautiful.
While it wouldn’t be a mistake to only visit Tuscany, definitely consider Umbria and other nearby regions heavily into your decision as well. Even with a short time frame, you can see a lot in Italy. It is smaller than you think!
Some of my favorite spots in Viterbo & Umbria:
Tip 2: Pick a convenient rental pick-up & drop-off location
I did a lot of research on where to pick-up and drop-off our rental. I also did a lot of research on which car rental company to use. We ended up renting with Auto Europe due to online reviews and price. They were basically like Kayak, giving a list of different rental car companies to go with. I ended up picking a Fiat 500 or similar for $155 total for 5 nights. Bargain! And although the website said we might be charged a one-way drop off fee upon arrival, we never were.
We picked up the car at the Rome Termini train station which, besides the crowds of people, was a breeze. It was also a lot easier to get to than the airport for picking up since we were already staying in the Rome center. Everyone spoke English and after signing a few papers we went to get the car in the parking garage. The cherry on top was the rental itself. It was so cute! We named him ‘Chianti’, our wine colored chariot appropriately ready to take us through wine country.
After just only 10 minutes or so of navigating Rome traffic, we were on the highway. While a bit nerve-racking at first, it would be fine for any competent manual driver.
After our trip, we dropped off the car at the airport in Florence. This was an even easier experience. The parking lot was pretty small, and it was easy to find the Hertz spots. We handed over the keys, she checked the car, gave us a receipt and we hailed a cab to downtown Florence.
We definitely wished we had the car for longer. I would have loved to have it all through Italy. Still, it wouldn’t have made much sense unless we were heading to the coast or into the mountains. Most large cities (and some more popular smaller ones) in Italy have “ZTL zones” which are only for residents to drive through. This means, you can’t drive into Florence or some areas of Rome etc without getting a ticket. For this reason, we visited Florence, Bologna and Venice all by train. There was no need for a car in those places.
Tip 3: Make your life easy and have international data
With Verizon, Jordan paid the $10/day to have calls and data on his phone. This really made our trip a breeze. We used Google Maps for driving directions. We were able to look up historical information or restaurant recommendations on a whim. I could search for convenient parking lots before arriving somewhere. And most enjoyably, we got to plan the following day’s stops while having early evening cocktails without having to rely on WiFi. It just made everything so easy and stress free.
Additionally, having the ability to make phone calls was surprisingly useful. In Italy, most popular restaurants (expensive or not) require reservations! Instead of having to stop by the day before or during the lunch hour, we just gave them a call. This drastically improved the ease at which we had amazing meals around the country.
If your phone plan doesn’t come with an economical option for data and/or calls, I noticed a sim card stand upon arrival at the Rome airport. Many people were stopping by to pick up a temporary phone/data plan.
Tip 4: Stay at an “agriturismo”
For me, one huge bucket-list item on our trip to Italy was staying at an agriturismo, or farmhouse, in the countryside. While the quality and characteristics of these can range drastically, to put simply, an agriturismo is a room rented out within a working farm/farmhouse. Many of these are very similar to Bed & Breakfasts. Today though, many aren’t really farming as much as you’d think. Still, most are in beautiful stone homes built hundreds of years ago set on sprawling green acres of land. There are hundreds and hundreds around Italy.
There are many websites where you can search for these properties to stay at. I started using a few, such as Agriturismo.it, but with no luck. I would message properties and no one would message me back. I was starting to get discouraged and the search was overwhelming.
Eventually, I decided to narrow down an area I’d want to stay in and set very specific amenities I was looking for. For me, it was an agriturismo in the countryside with either a well-reviewed restaurant or even better– owners who cooked traditional Italian dinners. I started searching on Booking.com and found Tenuta il Casone and was sold. On Booking.com I was also able to instantly book.
Staying there was a dream. The breakfasts were a beautiful spread of homemade breads, jams and cakes. They cooked us dinner one night and it was mouth-wateringly delicious but simple. The other night there we drove to the small village nearby for the best truffle pasta I’ve ever had.
Even though I could of stayed a week, two nights was perfect. The price wasn’t bad either, we paid about €150 total for both of us, not including €20 each for dinner.
Tip 5: Read up on the rules of the road.
The easiest and cheapest cars to rent in Europe are manual cars. Given I can’t effectively drive a stick-shift, Jordan did all the driving. He did a few very useful things before picking up the rental others should note:
- First, he read a few articles on Italian road signs and tried to remember what they meant.
- Next, as we walked around Rome we practiced recognizing the signs. Beware: These are very different from U.S. road signs and the symbols won’t instantly make any sense!
- Lastly, recognize where ZTL zones might be (you can’t drive in them!) know what their signs look like.
- This may seem intimidating but it is actually pretty simple. For ancient/medieval walled cities it is pretty certain they will have a ZTL. For this reason, we ALWAYS parked in a lot or garage right outside the city walls. From there, there was always an escalator or elevator to take us inside. Every one of these towns in Umbria and Tuscany is walkable (i.e. Orvieto, Pienza, Assisi, Siena) and there is no need to take the car inside. We usually parked, walked around for a few hours and had lunch, then continued on to the next stop.
What our basic itinerary looked like:
1 night Orvieto (hotel), 2 nights near Citta della Pieve (agriturismo), 2 nights outside Siena (Airbnb)
We picked-up car at Rome Termini at noon. First, we drove to fascinating Civita di Bagnoregio for a wander. After that, we took the smaller, windy roads to Orvieto with photo and snack stops along the way. At the base of Orvieto, we parked the car in the big garage and took the long escalators into town to check into our hotel. That night we had an amazing evening of wine, wandering and fabulous food. Don’t miss getting lost in Orvieto’s narrow allies at night!
Today, we drove through the beautiful countryside to Assisi. Parked at the main lot and explored the town. Assisi was very touristy and crowded on a Sunday, but well worth the visit. After a few hours, we drove to our agriturismo near the medieval town of Citta della Pieve. That evening we went into town for dinner.
Got our first taste of Tuscany today by driving through the famous Val d’Orcia and to Pienza. We feasted on amazing wines, pecorino cheese gelato and a white truffle burrata that I’ll remember forever. On the way back to the farmhouse we stopped by a cheese factory and reserved a tour for the following day. We then had wine & dinner at the farmhouse that evening.
We checked out of the farmhouse and drove back to Val d’Orcia to stop at the beautiful and sleepy Montecchiello. Next, we went to Fattoria Pianporcino for their 1pm cheese tour and tasting. We ate our hearts out…and then sneaked out the leftovers for road snacks. Finally, wrove to the outskirts of Siena to check into our charming local Airbnb. We had dinner that evening in the countryside at the most beautiful restaurant. (Every restaurant was!)
On this day, we explored Siena, had more amazing food and drove around the countryside. We savored our last night with the car in Tuscany. At night, we tried to cook real Italian pasta in our kitchen. This remains a work in progress.. 😉
On our last morning we drove through the heart of Tuscany up to Florence. We dropped the car off at the airport and said our goodbyes to ‘Chianti.’
Extra points to note on renting a car in Italy & doing a road trip through Tuscany:
- If you’re barely a competent driver in the U.S. or other calmer countries, don’t try in Italy. While it was fine for Jordan (and is for many good drivers), the roads are very narrow and the traffic can get tight. The countryside is nothing to worry about but I’d advise terrified/horrible drivers to yes, just take the train (or make sure you have good insurance).
- There are SO MANY beautiful places to visit in this area, and Italy as a whole. If we had more time I would have kept the car for longer and also visited Lucca and more of Northern Tuscany. Even better, we would of then continued on into the Alps! Given the price of the rental (around $32/day), it was very affordable.
- Don’t try to fit too much in. Most of our time in this area was spent leisurely walking around villages and sipping wine in beautiful locations. The freedom of having the car was a huge plus, but that doesn’t mean we wanted to spend all day sitting in it. Our furthest drive was probably only 3 hours total.
Overall, taking a road trip through Umbria and Tuscany makes for the perfect holiday. With Airbnb and economical car rentals, it doesn’t have to break the bank either. A few weeks out and I’m already thinking….can we go back yet?