A little Italian countryside road trip? Why not? We played it by ear this trip and would decide just where we were going to land each day after staying at the villa in Umbria.

So, when we headed out of Umbria and traveled on into Tuscany, we were not sure just where we were going to get to that evening. We packed the car, packed some food and hit the road and traveled through several regions, vineyards, mountains, fields and wonderfully charming people and little villages that appeared out of nowhere. We stopped to explore along the way but mostly took the roads less traveled into the mountains towards the sea. And where we found ourselves was on an idyllic countryside drive with beautiful magic filled moments.
Italian Countryside Back Roads
There were 2 trains of thought with taking the Italian countryside backroads while traveling. Not traveling on the mainstream roads -avoiding tolls and traffic and stopping at all the mainstream places- and focusing on rural- out in the middle of nowhere roads- basically, the roads less traveled. The more authentic experience rather than the tourist experience if you will. We speak little Italian- but do know conversational phrases and always speak in their language as much as possible. My husband being 1/2 Italian and looking Italian definitely helps. The Italian countryside villages there were off the beaten path and the places where tourists were not as common. We did stop at a couple of musts in the Tuscany area since we had not driven through before. But I have to be honest, because they were so overrun with tourists it made it harder to soak up their magic and enjoy them.

That said, the countryside roads to get to the villages along with the countryside views were incredible and that alone was worth taking the side roads to see them. We stopped briefly in Montepulciano, Siena and San Gimignano along with a couple of other small villages- they were all quite busy but beautiful so if visiting the villages is your thing- put them on your list!

The countryside back roads took us through the mountains and rolling fields. Absolutely breathtakingly beautiful. I highly recommend taking the roads less traveled if driving in Italy. There were small villages that would pop up, country roads that were more dirt than pavement and so much untouched natural beauty. We made our way through Tuscany and over to the coastal region below Cinque Terre where we were staying in a little boutique type hotel on a working vineyard/farm.

Country Living
The hotel in the Castigioncello region was absolutely charming. It was near the coast set among vineyards and with fields and farm animals all around. We fell in love with the simple beautiful charm the area had- and the folks running the hotel were absolutely lovely. We enjoyed a nice conversation with the owner and she was so sweet and helpful in pointing us in the right direction when we left the next morning.

We made our way up through the mountains again on the backroads on the way to Sestri Levante. It was just a few hour drive (on the backroads) though it was storming while we driving so it took us a bit to get there. Again- the mountains were incredible.

We absolutely enjoyed the drive and when we came down the mountain to Sestri Levante- we were mesmerized. We had heard that Sestri Levante was a perfect spot for enjoying the coastal Italian views similar to Cinque Terre and Portofino- but without all the tourists which is why it made the list to stay in. It did not disappoint.

Such a charming, beautiful seaside town that was full of friendly folks and lots of ambiance. We wandered the village streets, sipped cappuccino (again) and soaked up all the beauty this little spot had. The next day, we were supposed to be on the way to France- but my husband wanted to stay one more day in Italy and so, we stayed in Santa Margarita which is near Portofino. We had not been to Portofino before, so since we were so close, we broke the touristy rule and stopped to say hello.


We explored the village and areas of Portofino and then headed on through some of the little village areas around it. Portofino was highly touristy – I honestly think we heard more people speaking English there than anywhere we had been in Italy- and it was so busy vehicle traffic and foot traffic wise so something to note if driving in or visiting. It can make you a bit jittery on the one car size roads with all those buses, cars and people. But it was a beautiful spot- we enjoyed a gelato and cappuccino there and did a bit of hiking.


Genoa and Avignon, France
The next day in adventures of dropping the rental car off at the airport in a very large busy city area- between road construction, closed airport roads, toll fines and more- all before 10am- it was a bit much. I will be honest. The biggest issue with driving in Italy was navigating all their road laws. Oy vey. We were pretty frustrated with the airport car situation after going through all the roads once, paying a toll and them sending us back through the toll area again when the road was temporarily blocked. We ended up getting off the freeway and parking on the side of a small road to change the drop-off location to a Genoa train station. We got honked at and yelled at briefly haha and then a maritime officer helped point us in the right direction. When we got to the train station, we found no one there to accept the car drop off. Of course. We left the car in a designated spot. Documented everything and called the company to let them know. Which led to us being cut off on the phone more than once trying to get it all sorted.
By the time we got on the train to France – we were more than a little over the frustrations and ready to chill and not drive for a minute lol. Again, I have to hand it to my husband- I don’t know that I would feel comfortable driving in a foreign country- especially big city areas- but he took it in stride and it was absolutely the best way to explore. We saw so much more of the countries than we imagined we could-met so many wonderful folks and being able to trek around led to moments and memories full of magic that we might not have found. I highly recommend doing it if you feel comfortable! I will delve much more into what we learned, what not to do (ahem a few things) and what we are planning for the next trip soon.

Of course, after almost a week in Italy – we were excited to head to France and start exploring the countryside there too. We took the train to Avignon and stayed there for the night- it was so lovely to wander through their village market that evening and explore Avignon in the morning before the tourists were up.


You can read more about Assisi and Trevi HERE and our stay in Umbria in this post HERE.
Up Next – our first stop on the backroads in France and what we discovered.
Such a beautiful country. Looks like you had a great time!
You are brave…and, I forget, hopefully speak Italian. We did similar on our honeymoon, 1972…some things never change…franki
Except for the rental car return, this sounds like such a wonderful part of your trip! I have enjoyed your photos of the beautiful Italian countryside.
so enjoyed seeing your pictures! thanks! you are blessed to have a husband to drive. my husband don’t like to drive locally to explore….
why are the streets empty? where are the people that live in these towns?
Not sure- maybe staying indoors with the rainy weather? We did meet a couple of locals in some of them while wandering- the villages were so beautiful.
This type of trip is the absolute best kind to do!! i have done ireland, germany, spain, portugal, france, italy and switzerland this way. Sometimes we make a few reservations prior to leaving home but mostly just take our chances on finding small, cute, unique, out of the way places to stay. we’ve never had a problem traveling this way and have seen so much more of how the people really live. of course, we make sure we see all the major, popular, touristy sites but, once we get those out of the way, we are off on our adventure! I travel with long time girlfriends and we never worry about getting lost. we just sometimes wind up somewhere we’ve never been before! oh, one more thing……….not a one of us speak any foreign language and that issue has never caused us a problem. as a courtesy to the people in whichever country we happen to be traveling in, we always know the basic words for thank you, please, good morning, good evening, good night, etc. your post makes me want to make some phone calls “to plan a trip”! thank you for sharing your journey with us.
Several years ago there were three lovely women in their 60’s who lived in west michigan, and they decided to visit tuscany for ten days together. One of them (me) foolishly volunteered to do all the driving as, like you, we were delighted by the prospect of seeing the “real Italy” and that meant being on our own schedule and driving ourselves wherever we went. Our teeny tiny rental car had a manual transmission by the way. now, I’m an optimistic person by nature, which helped, but since i was the only driver i must say that by the end of the 10 days my nerves were a little shot; having said that, being on our own and driving through the winding roads, small villages, and wondrous sights of tuscany was absolutely the right choice for us. The places we saw! The food we ate! the people we met! the surprises we found around every corner – were truly magical
We too visited Montepulciano, Siena, San Gimingiano, as well as cortona (the small village that was the inspiration for the book and movie “under the tuscan sun”), the chianti region, and the beautiful city of florence. since we “got lost” several times we were often asking for directions from the people who lived in the area, and who were most welcoming and eager to help us. Every little town has a piazza, and we found that by mid-moring the elderly gentlemen of the village would all gather on chairs there and watch the world go by. We could always count on them for help.
there’s something very mystical and magical about tuscany. we always felt enchanted by the sense of history that surrounds you at all times as you wander through the villages and the countryside. for example, one day we came upon a shepherd and his flock of sheep and watched them contentedly as they slowly crossed the dirt road in front of us. another day we serendipitously landed in arezzo on the same day that they were having jousting tournaments and contests with a neighboring village. all of the participants were colorfully dressed in their full regalia, and later there was a wonderful parade through the streets following the contests. and the food! every day was a gastronomic adventure. italians know how and when to eat. everything is made fresh every day, and most meals don’t start until late evening and take at least two hours. we found that the more out-of-the-way the restaurant the better the food. fresh caprese salad with olive oil and basil and homemade pasta were my favorites, especially if followed up by a cup of gelato.
Well, thank you for allowing me to go down memory lane. i so enjoyed your post about your own adventures in tuscany and that got my heart racing and wanting to return there. italy is just that magical!
We are currently in Milan after several days in Florence and switzerland. Renting a car and being free to explore, like we also did 30 years ago on honeymoon is the way to go. This time with 4 of our kiddos we stuck to trains and tours. Not quite as adventurous, but beautiful! Highly recommend Cinque terre!