If I were to do my first Italy trip again, I would change the pace of my trip. My first trip to Italy in 2013 was about 15–18 days long and, on paper, it looked perfect. I was going to a lot of places, seeing cities, towns and even small villages. But there was a problem! I travelled from the north to the centre and then back towards the north, moving every two or three days from one hotel to another, from a bed and breakfast to a hostel. It was beautiful but so very exhausting. And looking back, I don’t think I took it all in.
I was in my 20s then, and I was definitely in a different frame of mind. I had the energy to keep moving, and there was that feeling that if I had travelled all the way to Italy, I needed to see as much as possible. But even if I were 20 today, I don’t think I would do such a hurried trip. If I could do that first Italy trip again, there are a few things I would change.
1. I would slow down
This is probably the biggest one. I would choose fewer places and stay longer in each one.
I know why people want to see everything. Italy is one of those countries where every city seems to have something you want to see, and if you’re travelling there for the first time and especially if you don’t know when you’ll return, it is very tempting to fit as much as possible into one trip.
But I now believe that choosing fewer places and staying longer in one place is the whole game in Italy. Actually, I think it’s the whole game of travel.
That’s how you begin to understand a culture. You notice what happens in the morning, you find a café you like, maybe walk down the same street twice. You even start to recognize a shopkeeper, sit in a piazza without needing to photograph it and start understanding the rhythm of a place. On my first trip, I was always going somewhere else. Now, I would want to stay long enough to simply be somewhere.
2. I would spend my money differently (especially on food)
My first trip was a budget trip and because I was travelling on a budget, I ate quite a lot of food that, looking back, wasn’t really the experience of Italian food I wanted. There was supermarket food and food from touristy places. There were meals that were convenient rather than memorable. So if I were doing that trip again, I would be more intentional about where I spent my money. I wouldn’t necessarily spend more but I would spend it differently.
I would look for simple trattorias, good restaurants, small bars and places serving local food that isn’t necessarily expensive.
Because some of my favourite food memories from Italy have never been about the most expensive meal. They’re about sitting somewhere simple and eating something that feels connected to the place I’m in. I think that’s something I understand much better now after so many more Italy trips.
3. I would be more mindful about who I travel with
My first trip to Italy wasn’t a solo trip. It was a shared trip, although it didn’t quite unfold in the way I had imagined. I don’t want to go into the details of that experience, but it taught me something very important about travel: you need to know who you’re travelling with.
There can be a huge emotional mismatch when you’re travelling with someone and things don’t align. Travel amplifies everything because you’re together all the time, making decisions, navigating unfamiliar places etc.
Small differences that might not matter at home can suddenly feel enormous when you’re travelling. So if I were taking that first trip again, I would think much more carefully about who I wanted beside me. Because where you go matters. But who you experience it with can completely change how you experience it.
And that is why after my very first trip to Italy I always traveled solo until my honeymoon in 2018.
4. I would pack much less
This one makes me laugh now!!
On my first trip to Italy, I carried so many clothes. I had imagined one or two outfits for every day. And in reality? I wore about half of them. I was carrying so much excess luggage that I think I was, in some way, over-preparing myself for something. Now I would pack much lighter. Not just because it is more convenient, but because there is something freeing about carrying less. And yes, this is also my message to all the women who are listening: it is okay to repeat outfits.
No one really cares.
At 40, I’m realizing how much you can change an outfit simply by changing one piece. A sweater can be worn with jeans, with a skirt, under a jacket. A shirt can be styled in completely different ways. You don’t need an entirely new outfit every time you leave your hotel. I would rather have fewer clothes and more freedom. Because ultimately, I’m travelling to experience Italy, not to stage a different outfit every day.
My first Italy trip wasn’t perfect
And I’m glad it wasn’t.
Because that first trip was incredibly formative for me. It gave me so much strength and alignment. And, perhaps most importantly, it made me think about how I actually want to travel!
I don’t think travel is about doing everything perfectly. Sometimes you take the exhausting trip. Sometimes you overpack. Sometimes you eat the touristy food. Sometimes you travel with someone and realize you shouldn’t have and all of that makes you learn.
The more I travel in Italy, the more I realize that I don’t want to rush through it. I want to sit with it, notice the small things, eat somewhere simple, walk without a plan and maybe even stay long enough for a place to become familiar. And if I could go back to that first version of myself, I think that’s what I would tell her that you don’t have to see all of Italy all together or cram things up.
I hope you enjoyed my two cents here and hope it gave you food for thought.
This post is also published as an episode of The Italophilia Podcast, where I reflect on what I would do differently if I were taking my first trip to Italy again. Listen to the episode here
Thank you for being here!
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