Driving Map of Tuscany Italy – The Road Trip You Should Take!

Oh Tuscany?  Just the thought conjures up images of rolling hills, quintessential cypress trees, age-old stone villas…and an overall sense of euphoria and relaxation.  The ideal way to visit Tuscany is to rent a car and explore on your own.  On this road trip, I was lucky enough to bring one of my best girlfriends.  After all, who would say no to eating and drinking their way through Tuscany?  So here is our driving map of Tuscany, a road trip you absolutely must take!


Renting a Car in Italy is the Best Way to See Tuscany!

Tuscany is a popular destination in Italy, unfortunately, most travelers to Italy barely spend time in this amazing region!  It’s understandable, after all, there is a lot to see and do in Italy…and most people don’t have a month to explore!  But if you are lucky enough to get upwards of two weeks for your trip, then you should absolutely spend at least a couple days in Tuscany.

Many people choose to take Tuscany tours.  While group tours are fun and easy, they can leave you feeling a little constrained if you yearn for the freedom to get out and explore on your own.  Day tours of Tuscany from Florence are also quite popular; however, it’s not possible to really experience the beauty and relaxation of Tuscany in a hurried day trip!

After our experience renting a car in Italy to drive around Tuscany, we are convinced that there is NO better way to see Tuscany than by car.

Driving around in beautiful Tuscany, Italy!

Where to Pick Up Your Tuscany Car Rental

Most people will fly into major cities of Italy, such as Rome or Florence.  We actually spent a few days in Rome before taking off to the countryside.  Now, a quick note on driving in Italy…it takes nerves of steel!  And driving anywhere near the city of Rome can be overwhelming, especially if you are not familiar with driving in Italy.

Because we didn’t feel like dealing with the craziness around Rome, we decided to save our sanity and take a short train ride from Rome’s city center to Orvieto, a town on the outskirts of Tuscany.  From there, we exited the train station and picked up a rental car at the Hertz Orvieto station office, which was just a few minutes walk away.  Then we were off!
Before we knew it, the gorgeous landscapes and colors of Tuscany in the Fall welcomed us.


Driving Map of Tuscany – Our Driving Route of Tuscany Italy – More Time Always Needed!

The best way to experience Tuscany by car is to get off of the motorway and drive the winding, narrow roads throughout the hills.  Your view will be ever-changing with ancient hill-top towns, stone villas, and fields growing all sorts of beautifully colorful crops.
Our trip was during the Fall, which certainly brought out the vibrancy in the landscapes.  If you plan your trip right, you may be able to experience the harvesting festivals that are held in many of the small towns.  Usually they are held around the end of September / beginning of October.
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We loved meandering all around on the back country roads.  We turned off onto dirt roads, connected back to the highway, and wound all around.  It’s useful to have a GPS, or use your phone, just to be sure you don’t get totally lost.  But we loved the freedom of just exploring however we wanted.
Although we did a lot of driving, we wish we had a few more days because there were some areas we didn’t get a chance to drive through and popular towns that we didn’t get to visit.

Visit the Many Hilltop Towns Dotting Tuscany’s Countryside

One of the best things to do in Tuscany if you have a rental car is to stop at the different hill towns.  Most often, you will need to park your cars outside the city walls and hike up.  Once you are past the walls you will be greeted with narrow cobblestone lanes, and enticing aromas from the many shops.
Our favorite hilltop town was Montepulciano.  This adorable town was so quite on the day we visited.  It was a bit of a hike through the old city gate and up to the town square, but so worth it.  There were many shops to walk past, and quintessential back alleys.  Plus, there were some great views from the top!  Other popular towns to visit include Pienza & Volterra (which we didn’t have time for), and San Gimignano.  San Gimignano is actually quite touristy, but we did stop there due to the famous towers around town.  Just beware of all the tour buses!  Lastly, for a couple of girls traveling through Tuscany…you know we had to stop in the famous Cortona!
We had a blast sampling cheeses, wines, and olive oil.  We sat in old town squares and ate gelato while gazing up at the medieval architecture that surrounded us, and wondered what it would have been like to live in such a place back during its heyday.
And of course, we experienced lunches al fresco (and yes, all the food was absolutely divine!).
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The Best Part About our Route Map of Tuscany – Time to Relax in Quaint Villages!

The most wonderful part of our trip was that we chose to stay out in the countryside, at an agriturismo & working winery about 15 minutes from Siena on a dirt road.  The Castillo Di Selvole was an incredible place to stay — at a super affordable price!  The property was actually a historic, old property of a noble family; where they had a castle (now a Villa where the owners live), and a small village of farmhouses.
The 100+ year old farmhouses once were home to the workers who tended to the lands of the noble family.  They had been renovated to accommodate guests, like ourselves and had a refreshing authenticity to them, with wooden beams and simple, rustic furnishings.
The best feature was that each unit was like a mini-apartment, complete with separate bedrooms, and living / dining areas that included a small kitchen!  Having the kitchen was fabulous because throughout our daily travels we would pick up pasta, wine, cheese, bread, etc. and then bring it home to cook in the evening.
I remember so vividly sitting around drinking wine, cooking and chatting with my good friend.It was a wonderful way to spend each evening…we relished that time just relaxing and enjoying the good life in Italy!  The property also had a refreshing swimming pool that was surrounded by grapevines, and they were in the process of building a restaurant on site…in a building that has ties to the Templars!
** Side note:  This would be an awesome place to have a destination wedding — or just a family / group gathering!  You can rent out all the apartments, and they have a restaurant onsite as well as lots of great facilities & patios. 
Outside our farmhouse unit we were surrounded by vineyards.  If we had we come 1 week later we would have been there in time for the harvest, so the grapes on the vines were quite large and nearly ripe. While we didn’t get to see the harvest, the owners took us on a free, in-depth tour of the facility and talked about the preparations that were going on.
Being a small, friendly establishment, we were offered a free tour down into the 100+ year old cellars and got to listen to the owners talk about their age old wine making traditions.  The best part was that at the end of our tour we were able to sample some of the fantastic wines – free of charge.
Even better was the fact that our accommodation was quite remote, and there were only a few other families staying there at the time.  So rather than waste the bottles of wine that the owner opened for us to sample, she just gave them all to us to take back to our room for dinner!

Please…When Can I Return to Tuscany!!!

I simply cannot wait to go back to Tuscany.  The photos just don’t do it justice, and my descriptions here could never truly have an impact you the way experiencing it in person will.  In fact, while I don’t claim to be a world-class chef, I can cook quite well given the right mood and ingredients.

And I must say, I have never cooked as well as I did in Tuscany!

I don’t know how or why, but we couldn’t get over the fact that the meals cooked inside that little farmhouse tasted amazing.  It is as if simply being in Tuscany makes you a better cook, maybe it is the ingredients?  Or perhaps it was the euphoric state that we were in during the trip?  Or, quite possibly…it was all that wine we were drinking!

Whatever it was, I am excited to go back and do it all again.  Hopefully, for even longer next time.


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14 thoughts on “Driving Map of Tuscany Italy – The Road Trip You Should Take!”

  1. This is great. Thanks for sharing. I am planning to drive through Tuscany in June. I just had a few questions. Did you book your accommodation in advance or as you were travelling? and also could you drop the car off in a different city?

    Thank you

    1. Thanks for reading Bianca – and for the comment!

      We chose to book our accommodations in advance of our trip, just so that we would have the peace of mind. I am sure that during off season you can probably find places to stay at the spur of the moment – but we just didn’t want to waste time driving around trying to find a place to stay during the trip. But you could probably play it by ear and only book a day in advance, or maybe the day of if you look at places online and call them. Although, not everyone will have the best of English. It really depends on the type of place that you want to stay. But I’m sure you could make it work if you would prefer not to book in advance. There are pros and cons to both methods for sure.

      As for the car, we picked up our car in Orvieto and dropped it off in Pisa. Depending on the car company, you can choose to drop it off in another city. But typically, they will charge a one-way drop off fee. You just need to check in advance if they allow it and make the reservation accordingly. For us, it was worth the drop off fee not to go in a circle to return the car.

      I hope this helps. Have fun planning your trip. Feel free to let us know if you need any help or other recommendations.

      Happy travels!

      – Liz

  2. I’m just starting research a Tuscany road trip and absolutely love the sound ofT he Castillo Di Selvole! Thanks for sharing your route, very helpful!

    1. Thanks for reading Alana, and for the comment! I’m so glad to hear that you found it helpful. We loved the Castillo Di Selvole so much. I believe it has changed ownership since my visit, but it still shows up online for booking and looks as fabulous as ever. It was such a beautiful place that captures the essence of the region so much. I can’t wait to get back there!

      Happy travels!

  3. After reading your post, my husband and I have booked four nights at this location. We are having a problem finding a route to get there. Were you use Google Maps on your phone?? Any information you can give me would be greatly appreciated!!

    1. Hello Sherry – thanks so much for reading, and for the comment! I’m so happy that you have booked this hotel, it is one of my all-time favorite experiences from Italy!

      It is in the countryside just north of Siena. Here is a link to Google Maps – I have pinned it, so you can get directions. When I was there it was a few years ago, but the final 5 minutes or so is a dirt road — so keep that in mind. However, it was a wonderful little drive out there 🙂


      ** Oh, and the hotel should be able to give you some good directions as well. I don’t believe we used our phones — we just mapped it out in advance and used the directions from the hotel.

      Cheers to you & I hope you have an amazing trip!

  4. beautiful. was The Castillo Di Selvole your home base for trip? we are planning a week in Tuscany (small towns). do you recommend choosing a home base or staying different places? do you have suggest for website to locate good housing like The Castillo Di Selvole? thanks

    1. Hi Ron!

      Sorry for the delay, I’ve been traveling like crazy 🙂

      The Castillo Di Selvole was the home base for our time in Tuscany. We found that it was a fairly central location so that we could take the car exploring different villages each day. Personally, since most things we wanted to see in Tuscany could be covered with a day trip, we liked having just 1 “home base” for our time there. But we did move to Florence when we wanted to explore that city. Overall, I think having just 1 place to stay in the Tuscan countryside is sufficient. But some people would prefer to mix it up. We loved not having to move our luggage more than once – it gave us more time to relax and enjoy our time.

      I typically search many different websites to find a good price, Agoda (http://www.agoda.com/?cid=1647566) is my favorite followed by Booking (http://www.booking.com/?aid=843216). But for quaint homestays, we also like Airbnb. If you use Airbnb, be sure to get your discount coupon from us here: http://www.airbnb.com/c/jwilson250?s=8

      Happy travels!

  5. Hi …. thank you very much for your post and tips. Im from panama and im planning my trip to italy. About renting a car, can I rent it in florence and return it in siena? Thank you very much for your help.

    1. Hello Dagmar – thanks for reading!

      It would depend on the rental agency that you work with. If they have offices in both Florence and Siena, then you should be able to return it. But definitely check with them ahead of time to make sure. And you could have one-way drop off fees — so double check in advance.

      If that is something you want to do, then definitely you will need to search for rental agencies who have offices in both cities.

      Thanks and have a wonderful trip!!!


  6. Hi,
    I’m trying to remember what town my wife and I visited. I want to say it was San Gimignano, but I don’t remember it as touristy. I do remember there was a tunnel through the town wall on one side of the town. We walked through the tunnel and saw a restaurant or two down in the tunnel. On one side of the tunnel there were openings we could look out and see countryside. Do you know what town that was?

    1. Hi Steve – thanks for reading!

      Unfortunately, this could be many towns — as tunnels through town walls are quite normal in this region. I remember seeing this feature in San Gimignano, Siena, as well as Montepulciano. But I’m sure there other towns in the area that have this too. San Gimignano is quite touristy, but if you went there many years ago or on an off season travel day, then perhaps it could have been less crowded. San Gimignano has all the tall grey watch towers, that’s usually what makes it stand a part from other towns in the area.

      I hope this helps. Thanks for the comment!

  7. Hi, you say you wish you had more time to spend in the area… How many days did you spend and how many would you recommend if one wants to see the additional towns which you missed?

    1. Hi Annatjie – thanks for reading!

      That is a very good question! On this trip to Italy, we spent almost 2 weeks. But of that, only about 3-4 nights were in Tuscany (if I remember correctly). We honestly thought that would be enough, since we would just be driving around a bit and relaxing. But honestly, it was so enjoyable and truly relaxing that we both really wished that we could have stayed 2 more nights and still not be bored.

      I think that 4-5 nights would be alright — if you were limited on vacation time and wanted to visit other places in Italy. Otherwise, you really could do a full week in Tuscany and have a wonderful experience. It does depend on what you enjoy doing in your free time. The cities in Italy are magnificent — it’s true. Great museums and so much history. But they are big, crowded, noisy and busy.

      Tuscany was just a DREAM!!!

      I hope this helps. Have a great trip!
      – Liz

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