The perfect 3 week Italian roadtrip Itinerary

European summer just hits different. And do you know what’s good about European summer as well? The amazing roadtrips you can do because of the smaller distances. The top destination for roadtrips if you ask me is defenitely Italy. One can never do wrong with these scenic routes and all the incredible food. My husband and I have been on the road through Italy for 3 weeks and here’s our Itinerary with all the do’s & don’ts, yays & nays and of course plan changes. 


Day 1 – Milan

We kicked off our roadtrip to Italy with a 10h drive from our homebase in Belgium to Milan. Milan is not only well-known for its fashion and cute boutiques but also for the Duomo. It’s totally worth seeing the Duomo in real life. The architecture is just incredibly beautiful and did you know that you can even get to visit its rooftop terraces? Epic views ensured from here.  P.S. if you arrive between 7-8 am almost no one will be on the square in front of the Duomo and you will get the chance to take some amazing shots. 


Next to the Duomo you of course have to visit some other places as Galleria Vittorio Emanuele. A beautiful mall right next to the Duomo. For your information, you will want to visit the icecream stand here. You’d also love to take a stroll along Giardini Pubblici Indro Montanelli and of course Navigli. Navigli is Milan’s own little Venice where you can enjoy your aperitivo by the water ! P.S. if you are looking for a nice rooftop with views over the Duomo head over to Terrazza Duomo 21. 


We were staying in the region of the football stadion and left our car at our accommodation.  We just had to buy one metro ticket to get in the city and did the rest by foot. 

Day 2-4 – Cinque Terre

Next up was Cinque terre. A big 3 hour drive from Milan. A possibility would be to include Portofino and / or Genua if you have more time or if you prefer to adapt this itinerary which is only a 2h30min drive. 


Cinque Terre itself consists out of 5 small villages (Monterosso al Mare, Vernazza, Corniglia, Manarola & Riomaggiore). You can’t enter everywhere by car so the best option is to park your car at La Spezia or Levanto or to just even stay here. We stayed at the NH La Spezia which offered us free parking for our car and allowed us to monitor our car during our stay. The hotel itself was just a short walk (approx. 10 minutes) from the train station which is actually the best way to get to Cinque Terre & hop around the villages. We took a Cinque Terre card which grants access to all the hikes & unlimited train rides. 


We have stayed there for 3 days which was more than enough to do everything in a relaxed way. We did all the hikes. Spend some time at the beach of Monterosso with the cute beach umbrellas and did some dips in all the ports of Vernazza, Manarola & Riomaggiore. 

For dinner we can highly recommend having dinner at Nessun Dorma as the food is freaking good over there. For the sunset lovers amongst us we defenitely recommend to be at Vernazza or Riomaggiore.



Day 5-8 – Tuscany

Our next stop was the beautiful region of Tuscany. It was only a 2h30min drive to Florence where we stayed but of course we did visit some other charming places in the region as well.  


On the way to Florence we visited Pisa. When you think of Pisa you immediately think of the leaning tower of Pisa but actually this city is super charming. After visiting the leaning tower you should defenitely stroll around to discover it yourself.  The other places we visited were Lucca, Sienna & San Gimignano. 


San Gimignano is a very picturesque town where you can also find the world famous Gelateria Dondoli. So make sure you don’t leave without having that gelato!  Lucca is a cosy city famous for all its churches and Siena a lovely city very famous for its horse race run around the piazza that takes place two times every summer. We personally loved wandering around the cute streets of all these places. They just have such a delightful vibe. 

As we stayed in Florence we could spend most of our afternoons around there and we are happy we did so as this city is just divine. The Duomo di Firenze is the most beautiful cathedral we have ever seen. We have admired it from every angle and during every time of the day. In the morning when there was no one around and in the evening when the lights shone all up on it.


There are some lovely rooftops nearby from where you can admire the Duomo as well. We went to View on Art & Grand Hotel Cavour ourselves. Next to that, we really recommend visting Ponte Vecchio with its cute market stands and walking up Piazzale Michelangelo for a wonderful view among the city. It’s also a great sunset spot but it therefore can get quite crowded at that time. If you love pasta, and believe me even if you don’t you will do so after this, you have to get dinner at Simbiosi. They make their pasta homemade and you can take a sampling course so you can try different types of their pasta which is just SO freaking good! 



Day 9-11 – Naples

It would have made sense to head to Rome next but we wanted to keep this one for a seperate citytrip so we drove all the way to Naples. Naples is a 5 hour drive from Florence which is really doable.  We stayed in Naples for 3 days which we won’t typically recommend except if you plan to visit Pompeii & Procida island or take some time to chill. Naples itself is defenitely a must seen & done in Italy but note that the city is more dirty & has a different vibe compared to the other cities in Italy. They do however truely have THE BEST pizza in Italy ! 


Our favourite pizzerias defenitely were Brandi, one of the famous traditional pizzerias and L’Antica Pizzeria da Michele from Eat Pray Love.

For the city itself we just recommend taking a stroll around town, this is always the best way to discover a place yourself, but especially to walk all the way up to Castel Sant’Elmo. The views up here are pretty cool. And if you’re a football lover you defenitely want to make sure you see the wall art from Dries Mertens & Maradona at the Quartieri Spagnoli


A nice to know for your roadtrip is that from the moment we arrived in Naples we parked our car because people drive there like mad men. It’s not rare to drive with 4 cars next to each other on one lane. So be prepared if you decide to drive there as it’s not for the faint-hearted. 


Day 12 – 14 – Sorrento & Capri

After Naples we drove more south to a place nearby the Amalfi Coast and, which is according to us, the best place to start your Amalfi trip. Sorrento is a super charming town consisting out of tiny streets with shops and a lovely bay named Bagni Salvatore where you can cool down by the sea. We rented some chairs up at the deck there and spend a full day enjoying the sun and relaxing there! 


From Sorrento it’s also super easy to visit Capri. You simply take the boat at the port and you’ll set foot on Sorrento after a small 20 minutes trip.  Capri isn’t big so we found it perfect to do as a day trip. We strolled through town, went to chill at the famous La Fontelina beach club and rented a private boat. We highly recommend doing so because this way you can not only get to see all the beautiful sea caves and different angles from the island but you can really experience the dolce far niente vibe!





Day 15 – 20 – Amalfi

The most common and last stop of our trip would have been the Amalfi coast. This is also truely what we advise you to do. We had booked a B&B in Positano and planned on visiting Amalfi, Ravello, Atrani & Fiordo di Furore as well. Unfortunately there had been some issues with the mountains (Monti Lattari) which resulted in the closure of the scenic route from Sorrento to Amalfi. We drove back via the highway to Naples and tried to get into Amalfi via another way (by actually passing through the mountains) but we did not succeed. 


Instead of visiting the Amalfi Coast & leaving back home on day 21 we drove back up to Tuscany and enjoyed some last days at the Renaissance Hotel Il Ciocco Resort & Spa. 


Believe me when I tell you we’ve been to many different places around the world but that this has been one of the best trips we’ve already done so far. I do hope you can experience it yourself with this 3 week roadtrip itinerary.

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