The Best of Italy – Our Travel Itinerary

How to plan the perfect holiday in Italy? When to visit Italy? What are the must visit places of interest in Italy? Rome or Florence? Can you drive in Italy and is Venice worth visiting? 

The questions above are just a fraction of the million thoughts we had before planning our ultimate Italian adventure. Right now I am sitting on my terrace with a glass of Prosecco, listening to the musicians on the restaurant below me and enjoying the ineffable view over Positano … and writing this! 

I’m already a week into my Italy trip with Tanja and I wanted to share our brief Italy itinerary and hope it will help, entertain or inspire you!

First things first,

When To Visit Italy?

To begin with, I am definitely far away from being an expert on Italy so I’ll put this as it is. I really wanted to experience the best of what Italy has to offer. And for me, coming from a cold island in the Atlantic ocean – That means I want to experience all this during their calm weather, warm sun and in the blue!

I wanted to experience the best of Italy in the summer.

After a little research I found out that July + August are by far the most busy months for tourist and locals to travel in Italy. And the weather is just as perfect in June, July & August. Therefore, an early June holiday in Italy was perfect for us. We booked our flights to arrive on the 2nd. of June and departing on the 16th.

How to Plan your Italy vacation?

So, Italy is a huge country and WOW, there is a lot to see! Very much unlike my last holidays to Boston, Canary Islands and Morocco – I figured out early that there is no way to see everything in one trip and I had a seriously difficult time in choosing where to go, where to stay and what to do at each location.

I think the most common way to visit Italy or any country is to pick one location and stay there. For an example, a long weekend trip to Rome or Venice. Or a week or two at Lake Garda. However, I imagine it also must be common to do two cities at once. Milano and Venice or Florence and Rome. Since those are all relatively close to each other.

For me, I wanted to see as much of Italy as possible in the short time we had. But as I knew we would never be able to see even half of the beautiful spots we dreamed of, it took some time to crusade the destinations and choose what we would fit into our itinerary and what to save until later. We decided to visit the three largest “must visit” cities for only a very short time as we wanted to get to know them and experience what all the hype is about – But we didn’t want to spend our whole holiday in a city. We included some really exciting and more low key destinations in between cities and planned our holiday so that we could spend the last week on a beautiful beach somewhere … to get some tan on our skin and recharge the batteries before we head home to Iceland once again!

— Our Italy Itinerary —

Late night 1st. of June
Flight from Iceland to Milano (a very stressful but exciting 40 minute pitstop in Cologne, Germany in the middle of the night. Everything worked out even though we raced through the airport like crazy people). We arrived in Milan at 8am on the 2nd.

2nd. of June
MILAN. Basically, 1 and a half day in Milan.We also woke up at 6am on the 3rd.of June to enjoy a peaceful morning in Milano until 12am when we headed to the train station for Venice.  To begin with, we weren’t really excited for Milan but it was best to fly to Milano from Iceland. After our short visit, we loved it and will be back someday.

3rd – 5th. of June
VENICE and the incredibly & indescribably beautiful small town of Burano that is only an hour boat ride away.

5th. – 8th. of June
LUCCA (Tuscany). Or to be more precise, we decided to stay in the beautiful and very authentic small town/city of Lucca that is about an hour drive north of Florence. We loved Lucca and it was a great place to relax and enjoy the amazing Tuscan cuisine. From Lucca we did a day trip to Florence, Pisa and the Cinque Terre. It’s definitely worth mentioning that the Cinque Terre rivera is one of the most beautiful places I have visited in my life. Wow. (We visited Riomaggiore, Manarola and Vernazza out of the five towns).

8th. – 10th. of June
ROME. To spend only short 1-2 days in Venice, Florence and Rome might sound crazy to many people but we really loved this approach. We decided on just a handful of highlights that we wanted to see and still made sure that we would have plenty of time to relax, eat, drink and enjoy at each place. Out of the three major cities, we absolutely loved Rome and we have to pick it as a favourite out of the three.

10th. – 15th. of June
The AMALFI coast. WOW. We are staying for 5 nights in Positano and that is where I am right now as I’m writing this. Throughout our so far 10 days of travelling around Italy we have constantly been updating our “most favourite part of the trip list” … but I am so sorry – With full respect to every other place we have visited. Positano is by far the favourite. For the both of us.

15th. / 16th of June
We fly home to Iceland from Napoli / Naples. Since our flight home is really early we decided to spend the last night in Naples. Because of our unbeatable love for Positano and the Amalfi Coast I believe we will most likely stay here as long as we can but we still want to be able to enjoy Naples for a few hours … just to make sure that it is a worth another visit later on. Which I am sure of!


Just to make this trip even better, we picked a flight home to Iceland with a stop-over in Amsterdam for good 12 hours, allowing us to explore Amsterdam for at least 8 hours. Neither Tanja or I have visited this capital of the Netherlands before so we are really excited. I’m sure we will love it but it’s also the perfect way to find out if we want to plan a longer trip in the upcoming months or years.

How to travel around Italy?

Alright, another thing definitely worth mentioning is that to begin with, I always pictured our Italy trip as we would be driving around in our own car. For us that is just the perfect way to travel. We can be on our own pace, see and do whatever we like and when we like it.

I think that the most common way to travel within Italy is via their advanced train system. The trains go everywhere, every day, all day and it’s not expensive! So yes, that makes sense. However it’s not very great when you have heavy luggage. And as I’m travelling with my princess … combined we probably have 60kg of bags including dresses, 10 pairs of shoes, make up products and god knows what haha!

This is the fun part. Wherever we looked, on every single travel blog, tourist information page and Trip Advisor forum I read – Everyone said that you should NOT travel Italy on your own car. It said that Italians are crazy drivers, it is complicated, dangerous and every road sign is in Italian. Also, with all the small towns we visited we were told that the roads are too narrow and dangerous, you can’t drive there and it’s impossible to find a place to park.

With all this information, we of course decided to rent a car! haha.

And it turns out that it may have been the best decision of our trip. We love it. Definitely everything mentioned above is true, but it has all been alright. A few wrong turns here and there and some mixups because of the Italian road signs is a small price to pay compared to the complete freedom of our road trip and the sights we have seen on the way. It is absolutely awesome to drive on the small coastline roads in Cinque Terre and on the Amalfi coast and I have been feeling like a rally driver the whole time! Still, I can easily understand why many insecure drivers might feel terrified of it. We also always found a place to park in no time, maybe it’s because we are not into the high tourist season yet. But parking is expensive, we just think it’s worth it.

Where to book your hotel / accommodation? 

I always book all my accommodations on and I’ve been doing so for probably 5 years now. There I find the best selection of accommodations, perfect information about the property + location and it’s easy to see a lot of options to compare the prices.

Take a look right here to explore the hotel options for your next trip – And I think (I have been trying to make this work!) that you should receive a 15 EUR discount if booking though this widget!

PS. I usually book and plan my trips last minute and it works out fine. However, with two months in advance, everything was fully booked in Italy! Therefore, most of our accommodations in this trips are just average. If visiting Italy over the summer time, I recommend you to book in advance.

Conclusion and What to do in each part of Italy

Lastly, if you are wondering what to do in Italy or in each city or town – please don’t hesitate to shoot me a line in the comments below, via email or on Social Media. All my information are in the “About Me” and the “Get in Touch” menu bars above. I have also been sharing a lot on Instagram!

I would love to help and will get back to you asap. I might definitely end up writing a whole new blog post for each destination of Italy that we have visited and your questions might help and inspire me to do it even better. Just like this post is more or less inspired by questions through my Snapchat and Instagram 🙂

I really, really hope you have enjoyed the read and got inspired in some way. Please let me know what you think here below or on any platform. I would love the feedback! All the photos are from my Instagram or Instagram story.


Now, I am going to open up a bottle of Lambrusco and play cards with Tanja! We have a big day tomorrow as we will go on a boat tour around the Amalfi Coast and I am going to dive into some grotto’s!