My Recent Road Trip in Italy

For me, there’s no better way to see a country than via car; especially in Europe. A road trip in Italy is the only reasonable way to see a lot of the country and do it on your terms and at your convenience. A road trip in Italy is also just plain phenomenal. I just finished yet another road trip in Italy. Here is a recap.

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Cinque Terre, Manarola

Before you choose a route for a road trip in Italy or anywhere you need to look at a map and decide where you want to visit. For instance, I have been to Italy dozens of times before and I’ve thoroughly visited much of the country. However, all my visits have been over a 20-year period so things change and you forget so it’s always nice to go back to places and mix in new ones as well.

I had just gotten off my latest cruise in Venice so that was my starting point. I knew I had about a week and I knew I wanted to leave out of Rome because that’s where the Italian Open Masters 1000 tennis tournament was being held. So I had my start and end point settled pretty easily. Now I just had to fill in the blanks for my road trip in Italy!

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Venice

I knew I wanted to visit or revisit the following places for sure: Ravenna; San Marino; Bologna; Cinque Terre; and Siena. So I designed a basic outline in my head of what my route would look like and then I looked at a map of Italy to see what else I could visit by roughly following the outline.

map of my road trip in italy

I soon realized I could add awesome places like Modena, Parma and several small towns in Tuscany. Plus the drive itself was phenomenal and I was very excited to simply look at the countryside as I drove. Basically, I was pumped for my latest road trip in Italy!

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Rome, Piazza Navona

I also want to mention that I never book accommodation ahead of time. I don’t like to be beholden to a schedule when doing a road trip. So again, I have a rough idea but don’t book until I see how I am doing time wise and then I book accordingly from my cell phone as I go. This is how my road trip in Italy went down!


Day 1: Venice – Ravenna – San Marino – Bologna


I left Venice at the crack of dawn and bee-lined it straight to Ravenna. It was about a 2-hour drive give or take. Ravenna is a nice town best known for its early Christian architecture, which has earned it a UNESCO World Heritage Site. There are actually several sites that make up the World Heritage Site.


Without question, the coolest thing was walking into the Cathedral to see the frescoes on the ceiling. You kind of felt like you were in Saint Peter’s mixed with the Pantheon in Rome. I won’t pretend I’m the most knowledgeable architecture fan in the world but the sites are worth a look. As are the plethora of excellent restaurants in the old town-you can’t go wrong with lasagna and a cappuccino!

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Ravenna, frescoes

From Ravenna it was about 75 minutes or so to the Republic of San Marino. San Marino is one of the world’s smallest countries. I hadn’t been in over 17 years so I was eager to stop by. It’s amazing what you forget over nearly two decades. San Marino was both smaller and more beautiful than I remembered. Plus it was a lot steeper than I recalled as well! Or maybe I’m just getting older!


The entire country of San Marino is basically on the top of a mountain overlooking much of southern Emilia Romagna. The views were stunning and well worth the steep hike up from the parking lots below! For the record there is also a cable car although I didn’t take it nor know about it until afterwards.

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, San Marino

Aside from the view, San Marino is a cute country/town to walk around, grab some gelato, a coffee and a souvenir passport stamp. They sell them in the tourist office for 5 Euro. They also sell a lot of strange weapons ranging from guns to 13th century swords. I am sure there’s something to it but I didn’t look it up or ask anyone.


After a few hours in San Marino I decided to head up to Bologna for the night. It was about a 90-minute drive and I booked a hotel in the center of town off of Trip Advisor, which I never do. Trip Advisor said it was the 2nd best luxury hotel in Bologna so I booked it because the first was sold out. The hotel was terrible and my theory on never trusting Trip Advisor stays true!


However, Bologna was pretty fantastic as a city. I had only been briefly on a train layover many years ago and never got a chance to do anything. But I got a great restaurant recommendation from a friend called Osteria dell’Orsa that was phenomenal (try the tagliatelle Bolognese) and one of the top 100 rated bars in the world called Nu Lounge was there.


While I thought Nu Lounge was overrated, there was much to see and do in Bologna aside from just eating. I happened to be there on a Saturday night so the streets were packed. The piazzas were full of life and energy and I just strolled around. It was the perfect way and place to end the first day of my Italy road trip!


Day 2: Bologna – Modena – Parma – La Spezia – Manarola


No matter how late I stay up I always wake up early so I ended up leaving Bologna for Modena quite early. This was great because it gave me a lot of time to see and do a lot on day 2 of my Italy road trip. Modena was about a 45-minute drive. I went straight to the Ferrari Museum.

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Ferrari, Ferrari Museum, Modena

The Ferrari Museum in Modena is nothing short of spectacular. I’m not even a car guy but it’s worth a look. I found it way better than the Porsche Museum in Stuttgart. The layout was fantastic and as you might expect from Ferrari, it was done with style. There is actually a second part of the museum outside of Modena but I only went to this one.


Modena also has a lovely old town. The Main Square or piazza is very typical Italian and of course is the center of life in Modena. It’s small and easy to walk around with plenty of little side streets to stroll and cafes to have a coffee in. I think I had 3! From Modena it’s another 45 minutes or so to Parma.


I had Parma circled on my mental map from when I started this trip because I knew I wanted to eat there. I wanted to eat Prosciutto de Parma, Parma Ham, Parmesan Cheese and obviously pasta and wine. So that’s exactly what I did!

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Parma, Trattoria Al Tribunale

I did a little research and found what was said to be the best place in town for lunch called Trattoria Al Tribunale. It was packed on a Sunday afternoon but I managed to get a table and ordered enough food to confuse the waiter as to how many people were eating!


After crushing my food, I tried to walk it off for a bit in the old town. The old town in Parma is not as impressive as most other Italian cities you’ll see but in my mind Parma means one thing…amazing food!


From Parma, it was about a 2-hour drive to La Spezia. The reason I drove to La Spezia is because that’s where you get the trains to the 5 towns that make up Cinque Terre. Driving to those towns and parking is very difficult so the smart move is to park at the train station overnight and train into the town you want to see or stay in. The train literally takes about 8 minutes! Trust me that’s the move.


I chose to stay in Manarola; which is said to be the prettiest of the 5 towns. I was in Cinque Terre back in 2000 during my second backpacking trip of Italy after I graduated college. My 4 friends and I went and all I honestly remembered was the 5 towns hike.


Nowadays, Cinque Terre has become a big tourist destination and prices have risen significantly. Plus with the advent of apps like Instagram, everyone wants to get their photos of these picturesque little Cliffside towns. Who can blame them?

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Manarola, view, Cinque Terre

I stayed at a place called Giovanni’s apartments that I booked on Expedia from the train station in La Spezia. It was nice enough although overpriced. Plus it was at the top of the main road, which is up a very steep hill. So if climbing straight uphill isn’t your thing I’d recommend staying as close to the water or train station tunnel as you can.


That aside, Manarola is a great little town that you’ll get the hang of in about 5 minutes. All the action takes place by the water and the iconic photos are taken from the adjacent mountain. It’s a great place for a sunset beer. In town there are several restaurants all of which I hear are pretty good. I ate at Il Porticciolo and was very happy.


Day 3: Cinque Terre – Florence – San Gimignano – Siena


After getting my car from the train station in La Spezia, I was to head to Siena. GPS gave me two options of routes. One went through Florence and the other went through Pisa. I have been to both several times each and wasn’t too excited about either so I asked my Facebook and Instagram followers which city they’d rather see pictures from. It was nearly unanimous for Florence. Plus I got several people recommending San Gimignano, a town I had never heard of. Social media can be great sometimes!

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Florence, Firenze

So after 90 minutes or so I popped into Florence for the specific reason of taking this photo (above) from Piazzale di Michelangelo. I knew this because I have been to Florence so many times and I love the photo.


Next I headed to San Gimignano, which I absolutely loved! With the exception of very difficult and limited parking it was what you want from Tuscany. It had excellent views, a great old town, quirky piazzas and fun restaurants and gelato places.

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, San Gimignano, Tuscany, Toscana

San Gimignano was a great stop for my road trip in Italy but it’s also the type of place you could stay in for a night. It’s also a popular day trip for people renting villas in the Tuscan countryside or day trips from Florence or Siena.


Siena was another 45 minutes or so into Tuscany and the drive was excellent. I booked a hotel in the old town so I could walk everywhere. I had never been to Siena and it was always on my list so I was thrilled to make it happen finally. I wasn’t disappointed.

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Siena, duomo

The squares in Siena were as good as anywhere in Italy. The duomo square is home to a stunning cathedral with great photo opportunities. The main square is where they have the legendary horse race each year called The Palio. Having seen it on TV then seeing the square in real life, I find it hard to believe they have such an event in this public square. However, I am tempted to come back to watch it sometime. It looks like sheer madness.

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Siena, palio

Siena has no shortage of excellent restaurants but the top ones book up nightly during high season so book in advance to avoid being disappointed. My first two choices were fully booked but I ended up eating very well. I mean its Italy afterall!


Day 4: Siena – Montalcino – Montepulciano – Rome


Day 4 was without question my favorite day of my road trip in Italy. It was mostly through the stunning countryside of Tuscany. Tuscany is an area of Italy that is comparable with anywhere on Earth as being the most beautiful place in the world. It is really that gorgeous.


Originally my plan was to drive from Siena to Montepulciano then to Rome. However, upon checking out of the hotel I asked the lady working if that was a good plan or she recommended anywhere else. She downright insisted that I go to Montalcino as well. Who was I to argue?! So 45 minutes later I was in stunning Montalcino overlooking seemingly all of Tuscany! What a gorgeous place. I paid for two hours parking and 3 hours later I came back to see a parking ticket on my rental car. We’ll see how that ends up!

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Montalcino

Nevertheless, Montalcino was fantastic. It’s a place you just stroll around and get lost. You climb up the fortress and see the amazing views. You pop into cafes and have a coffee and before you know it you’re playing soccer with little local kids. It’s a dream of a place and Tuscany at its finest in my opinion.

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Montepulciano

From Montalcino, it’s about 30 minutes to Montepulciano. Montepulciano produces some of my favorite Italian wines so I was very keen to go there. I didn’t do much research and had no idea how breathtaking it was. Much like Montalcino, the views were to die for, the old town adorable and the food and wine was off the charts.


It would be hard to recommend a better few days spent than how I spent them in Tuscany. Perhaps renting a villa with a group of friends or family doing a bunch of daytrips would be the only better way to do it. Tuscany is unreal and Montalcino and Montepulciano are the jewels for me.


Then it was onto Rome for me. As many of you know I love the Eternal City and have been countless times and 3-4 times in the past few years. I had 3 nights in Rome and stayed right in Piazza Venezia.

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Rome

It’s always great being in Rome because I know some great restaurants and love hanging out in Trastevere where Taverna Trilussa is located. It’s one of my favorite restaurants in the world-you’ll thank me later!

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Rome, Taverna Trilussa

My main reason for being in Rome was heading to the Italian Open at the Foro Italico. This is one of the Masters 1000 tennis events that are just below the grand slams in terms of importance. It was a great set-up and a cool place to watch tennis. It’s the last tune up before the French Open at Roland Garros in Paris. I went to the Men’s Final there last year!

My Recent Road Trip in Italy, road trip in Italy, Italy, road trip, Rome, Foro Italico, Italian Open, Rome Masters 1000, tennis

My other order of business in Rome was to check out one of the top 50 bars in the world called the Jerry Thomas Project. It was a hidden alleyway speakeasy where you need a password to enter. It is now one of my favorite bars I’ve ever been to. What a place! It will surely be on my top bars in the world list I’ll be publishing later this year.


So that was my latest road trip in Italy. Again I have done several in different parts of Italy and many other countries in Europe. It’s the best way to see Europe. You don’t have to rely on trains; busses, timetables and you can go at your own pace and see what you want. I highly recommend any road trip in Italy or anywhere in Europe!

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  1. I want to do this exact trip! Thanks for the great trip report as I loved following it while you were on it via Facebook.

  2. You had a very efficient use of time for this trip. Did you feel you could’ve or should’ve spent more time at any of your stops? Although it seems like you know what you’re doing!

    • Thanks for noticing I’m all about efficiency! Honestly most of them I could’ve spent more time in but I’ve also been to most of them before and I’m sure I’ll be back again to many as well. I think Cinque Terre I could’ve spent a week on its own doing a day or two in each town. Also Siena is phenomenal so for sure there. Oh and any of the Tuscan towns if you’re with a partner.

  3. I’m hoping to go to Italy next summer so I was extra excited to see this post. What would be the best time to visit between May and Sept? I’ve heard that August is hot and a lot of things are shut down that month.

    • May or September is best as they are shoulder seasons. August is hot but everything is open. That’s when they make their money!

      • Thanks for the info!! I’m from south Georgia so hot is what I’m used to in the summer but a cooler time would be more apealing….

      • Gail Woloz says

        Hi Lee, As a travel agent, I loved reading your trip report – however, I’d like to correct you about “everything” being open in August. This is not a true statement. Many restaurants and the best ice cream places close in August. Those who own them head on vacation to the coast where it is cooler. I try to always avoid booking my clients for a trip to Italy in August. As you stated, spring and fall are the best times!

  4. I spend half my day dreaming of a road trip like this every day. Thanks for the inspiration!

  5. Same Day Agra Tour by Train says

    Amazing beauty you shared of Italy, its really enjoying place and destination you shared which is popular beauty of italy. Stunning photos you shared of that place.

  6. I road tripped through France last summer and it was my favorite vacation ever. I waffled between trains or renting a car but as you’ve mentioned, cars give you the flexibility to start as stop when you want. There are no schedules. The only thing I didn’t like was how many tolls there were and how much they cost and gas too was very expensive.

    • That’s a good point the cost of fuel and tolls in Europe can be high but rental cars themselves are quite cheap. But it is what it is, you pay for the flexibility. I mean you’re on vacation!

      • I couldn’t agree more – Italian road trips are amazing! But there are a few things to be cautious/prepared about 1) Hidden speed cameras 2) restricted parking zones 3) different road signs 4) lack of speed limit signs on highways 5)Other unknown surprises.

        1) On some of the highways in Italy, they have these automatic speed cameras with no cops involved and several months later you’ll be getting an email from your rental car company that you received a ticket. I had that happen to me the last two times I was in Milan and I was being very mindful of my speed. Unfortunately, by the time you get the ticket back in the States it’s several months later and additional late fees then apply on top of the actual fine. In addition, you car rental company will charge you a fee for the effort they had to use to provide the ticketing authority with your mailing info back home.

        2) In some of the historic areas of cities like Milan & Florence, there are several restricted parking areas – ZTL (“Zona Traffico Limitato” or Zone of Limited Traffic)—and it’s very easy to miss those signs when you park, resulting in yet another email from your car rental company several months down the road. They are also enforced by camera with no ticket or officer involved.

        3) Also, as easy to understand as most of the road signs are, it is helpful to do a little primer of European road signs in case you’re not familiar?. On my first time driving there, I saw a few signs along the way that I was not 100% sure what they meant, like the speed number in a blue circle.

        4) You will find that on some highways you can go for VERY long stretches without seeing a speed sign. You need to be aware what are the “pre-defined” speed limits on highways, smaller roads, etc. (Except when posted otherwise, the following speed limits apply: 130 kmph (80 mph) is the speed limit on highways in Italy. 110 kmph (68 mph) is the speed limit on non-major highways outside of major urban areas in Italy. 90 kmph (56 mph) is the speed limit on local roads in Italy. per a web search that I did)

        5) And finally, there are some things you wouldn’t think of – such as on the Amalfi coast, I was told that during high congestion traffic days, you are only allowed to drive your car on certain days – so, for example, if your tag ends in an even number, you can drive Monday and Wednesday.

        Sorry, this was so long, I just learned some of these the hard way on my recent 3 week trip throughout Italy.

        • Alisson from Malaysia says

          Hi Yvonne thanks for the tips on driving in Italy. I am tempted to do a road trip in Italy this June with my family but after reading about all the limitation in driving to the city centre it sort of put me off. But with kids and suitcases driving is still easier than taking the train.
          Can you share with me how did you travel in the city centre? Did you park your car on the non ZTL area and use the public transport or walk to the city centre?
          In Florence should I stay in the city centre or in an area which allows me to drive?

  7. Christine says

    Thanks for sharing this! I was one of the people begging for your itinerary as it looked amazing! I can now see and confirm it was just that! Thanks Lee!

  8. The Italy is a perfect place in the world to visit … love all the ones on this list! Awesome pics.

  9. amazing pictures.Thanks for sharing information with us

  10. What a great list you have. It feels like Italy is the best place to enjoy. Lovely pics.

  11. Thanks for sharing this

  12. Ahh…Italy. The country is just simply gorgeous, I especially love the tiny quaint villages around. How was it driving around the country?Thanks!

  13. Italy is so beautiful. You picked such an amazing route. This summer will go the same way.

  14. i got the bolognese pasta in pictures frame. its the most yummy thing in Bologna. Your route is the best. Why didn\’t you make it a little long to puglia and napoli?

  15. Great post, Lee! This is absolute #goals!

  16. Italian food is always i like to eat and wish to eat whenever have a chance, these pastas are my favorites as a food lover.

  17. I will drive from Venice to San Marino, but I am puzzled if train is a good option. Some fellow traveler recommended the car drive is not so good in this route. What is your opinion please.

  18. Going to give the car route a try in Sept. group of 6 so we needed to rent 2 cars. Going from La Spazia to Sorrento by way of a lay over in Sienna. I am apprehensive about taking cars but majority ruled this decision. Hope I don’t want/need to say “I told you so” – especially based on comment provided by Yvonne!

  19. I love to have this amazing trip once must in my life. I love to visit Italy.

  20. Alisson from Malaysia says

    Thinking of making a road trip from Milan to Parma to Bologna and Florence but after reading about the ZTL which applies to most of the major city it sort of put me off. I then came across your blog and would really like to know how did you go around the city centre? Did you park in the non ZTL area and take the public transport? Please share with me how you manage to move around all these beautiful cities with a car.

  21. Maribeth Southworth says

    So what\’s the password for the Jerry Thomas Project? 🙂

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