Italy Road Trip - Naples to Milan

October 8, 2020
This road trip in Italy was absolutely amazing. We went from Naples to Milan, of course you can also turn it around, this just suited our flights better. I like combining exploring important sights with getting the best from local advise, so you really feel the country you´re visiting. Therefore I dont prefer big groups and tourbuses I stay away from like the mosquitoes frankly. There is easily possible often to find alternatives that don´t even need to cost more. Here is our schedule in Italy, I hope it comes in handy for you:


Arrival in Naples

Arrival in Naples

We arrived in Naples at noon and picked up our rental car from AVIS. I wanted to experience real Italian countryside and cuisine. Preferably food by an Italian grandmother to get the real thing, while also seeing the sights and trying restaurants. Our combination was pretty much to get the best of everything and take the experience all the way.

We stayed at the most amazing place called Olivara Sorrento, which is an agriturismo place. It was really one of the best parts of our trip to Italy and complete highlight! The location is perfect for staying on the Amalfi Coast, only 2km from Sorrento and 8km to Positano. The view from the house is amazing, they grow olives and lemons. I got to pick the biggest lemon I have seen in my life before breakfast! I couldn´t recommend this place more.

That evening we walked through famous Positano, looked in a few shops and enjoy the narrow streets. We had dinner reservations at Mirage in Positano that evening. I can wholeheartedly recommend that restaurant, beautiful views and the service and food was fantastic as well.


Pompei and cooking class

Pompei and cooking class

The following morning we had booked this tour with Airbnb Experiences in Pompei from 10-12. I really love that feature on Airbnb as you can find very small groups to go on, we had only 4 other people with us. The guide is doing it really out of passion and you feel it is not only a 9-5 job. We learned so much and I recommend this tour. Pompei is so big, it really is worth it making the most of it with a planned 2 hour tour. We booked lunch at Vincenzo Capuano Pizza nearby. They were amazing!! (droool drool..)

That evening we had booked at our Agriturismo stay Olivara Sorrento, a private cooking class. It was not much more expensive than going to dinner, but a lot more fun! We learned a great deal and they were so nice and kind to teach us a lot.


Positano beach day

La Banhina Positano

We booked the Arienzo Beach Club, which is a private beach a few minutes by boat from La Banhina Positano. It offers a superb restaurant as well and they take a certain number of people so it is never over crowded. It is really THE top choice if you want to sunbath in Positano without the crowd and noise. Just remember to book very well in advance, and a lunch table as well.

After spending the day there, we returned our rental car to Naples and took the train to Rome.

DAY 4 & 5



I recommend taking the train into Rome and be rid of the rental car there. The road trip in Italy was for now more of a train trip. It is both easier than finding parking places, and frankly driving there does acquire some skills.

While staying in Rome we booked an airbnb apartment in Trastevere. I fell in love with that neighbourhood. There was something so utterly charming about it in every way.

We booked this tour to the Colloseum with Airbnb Experiences, I can really recommend it, even the kids loved it! It was not only educational but also the way Alfredo, our host, made the tour so much fun. He really made the Colloseum come alive for us with his playful skills and stories. It was truly amazing and my daughters best part of the whole Italy trip.

We walked around Trastavere and enjoyed some free time in Rome. It is a truly beautiful city with so much history, I recommend not booking too much, just taking it in by walking, Sometimes the best things are the ones you just stumble upon. As this precious photograph here below confirms.

Tour in Rome

Er Buchetto is a nice and really local old fashioned lunch place, since 1890. I also loved Augusto restaurant in Trastavere, it is very local and only has an italian menu set each day. Means you maybe have no clue what you will get, but I can promise it will be delicious!

DAY 6, 7 & 8


Florence, Italy

We continued the road trip in Italy and took the train from Rome to Florence around lunchtime. If I could change anything, I would have wanted an extra day in Rome. We stayed at Forte16 Florence. I liked the location, though the hotel only had an inside swimming pool in the spa and outside jacuzzi. Especially with kids, an outside pool is better.
Florence is an amazing place with such rich history. I really loved the city and finding local places to eat was quite easy. I especially loved popping out for breakfast and seeing the morning come to life with Italians everywhere – having coffee and a simple yet delicious breakfast.

We booked the Galleri Uffizi while in Florence which is a must see. Just remember to book well in advance before your trip.

I also recommend getting to know the Medici family more, here is a tour in Florence. You can also watch the TV show on them while looking forward to the trip, just makes Florence even more intriguing.

Florence is one of the most beautiful cities I have seen. So if you have yet to do a family photograph, I recommend doing it here. I booked with Shin Jae and loved the photos. Photos really help memories come alive. He also showed us some breathtaking places we would not have known about in Florence.

From Florence we took a train to Milan and went straight for the airport. I loved the road trip in Italy, it is an amazing country that I cannot wait to explore more!

I hope the post helped if you are planning a trip, let me know if there is anything you want to read more about Italy for another post.