After my grandiose announcement of moving to Italy, I feel as though I might be coming up short on what to share next.

I’m in a major period of transition and am unable to answer seemingly simple questions from people such as: Where in Italy are you based? Thinking about how to respond to this seemingly innocent inquiry gives me MAJOR ANXIETY. It sounds too permanent.

I’d like to rephrase the question and change it to: Where in Italy are you based right now?

There. Now I can breathe and give you a more accurate response based on my emotional state. :)

We are currently based just outside of Milan and have been here for one month now. One month! While I can say with certainty that Milan isn’t home for the long run, it has been an “easy” place to land (we have family here) while I consider the big questions:

Where is the best place to raise my daughter? Where will I feel happiest?

Historically, I’ve chosen where to live based on a feeling and can discern pretty quickly if somewhere is, or is not, for me. I’m a Reflector in Human Design so my environment is absolutely critical to my happiness. (I believe it’s critical for everyone, but I am incredibly sensitive to my surroundings.) I’m sure a feeling is what it will come down to for me again, but I can’t help but want to formalize the process and take my time now that I have a little one in the mix. (I also want to speed things up because I have been so restless and dare I say somewhat depressed in my current circumstances. The duality of it all…)

When I first started traveling and living abroad full time in 2016 (my post divorce era), I would Google blogs about a specific city, connect with expat groups on social media, pick my first Airbnb/hostel/volunteer site, and then venture out on a one-way ticket, deciding how long I wanted to stay after I arrived. I did this for my Latin American backpacking adventure, Mexico, and Italy (the first time around).

Now I view things a bit differently. It feels as though there’s too much at stake to consider such a laissez-faire approach. Arriving in a foreign country with a toddler (and all of her things) in tow does not make for the simplest of transitions. I want to do more research, look into the family scene, understand the schooling options, and do trial trips to uncover what it might be like to really live somewhere. I also have to LOVE IT, of course. I have needs too.

Since I’m not ready to hop on a flight or a train and explore IRL just yet, Substack has been immensely helpful. I’m following other expats who have chosen to base themselves in Europe, reading incredibly insightful articles on what it means to create community and start a new life abroad, with or without a child. I suppose it has also been slightly unhelpful too, in that I kind of want to move everywhere, including France, which was never on my list before. If you’re someone who writes about, well, anywhere, please share your Substack with me below so I can imagine a day in the life in your city and country of choice. :)

The Virgo in me is also very happy to start with a checklist. To help me turn this huge decision into something more palatable (and fun!) I'm adding AI into the mix. I asked ChatGPT to give me some suggestions to get my creative juices flowing. Here was my initial (too vague) prompt:

Please help me come up with a list of cities to live in in Europe based on the following criteria:

1. Affordable
2. In or near nature
3. Good, clean air quality
4. Family friendly
5. Strong expat community
6. Coworking spaces and strong wifi

The first option was Ljubljana, Slovenia…Now, I have nothing against Slovenia (I’ve never been) but I was thinking of options a bit…warmer, and more specifically in and around Italy or Spain.

I decided not to refine my search quite yet and continued reading. There’s no judgment in the brainstorming process, right? Imagine my delight when I got to #4 and saw somewhere already high on my list of cities to look into: Valencia.

I know what you might be thinking. But Asia, Italy is your place!! I don’t disagree with you. I always feel the most excited, alive, and at home in Italy…and, I want to keep my options open. I’m trying to keep an open mind and heart as I consider the long-term implications of basing our little family somewhere. It isn’t all about me anymore, and I know that wherever my daughter is raised will undoubtedly help shape her.

Thinking about this makes my head spin. The US is getting scarier by the minute, and while there are many things that I absolutely LOVE about Italy, there are also things that make me cringe (like anywhere to be honest). I’ve heard that Spain is “family friendly” but I haven’t yet experienced this for myself. I know nothing is permanent and that I can always pivot. I’m SO GOOD at the pivot. But I really want to find a place that sticks this time around. If it doesn’t, maybe my daughter will be content to move around a lot, similar to how I grew up, but I don’t want to get ahead of myself. Moving 24/7 is quite exhausting. I’m not in my 20s (or 30s) anymore!

I am also deeply craving community and want to put down roots somewhere, while also staying connected to the other communities I’ve created around the world. The sadness of always leaving by Russell Max Simon does a beautiful job summing up how I feel.

The answers to the bigger, philosophical questions obviously need more than crowdsourcing or an AI prompt. To truly understand the intricacies of living in a new city, you need to spend time there, and if you’re anything like me, to feel it out.

Not wanting Slovenia to show up in my search results again (the average temperature in Ljubljana is 10ºC, reaching -28ºC between October and May…no thank you!), I updated my prompt to the following:

Please help me come up with a list of cities to live in in Western Europe based on the following criteria:

1. Easy to live on $X,000 USD per month (I kept adjusting this number, but did you know the average monthly salary in Italy is 1,400 euros (net)? I’ll leave it at that.)
2. In or near nature
3. Good, clean air quality
4. Family friendly
5. Strong expat community
6. Coworking spaces and strong wifi
7. Running community
8. Montessori or Waldorf schools
9. Warm climate

You’ll notice in this version that I have a mix of practical aspects (such as a specific budget range, ease for remote work, and ideal weather conditions), as well as some more values-based criteria (such as running community, family friendly, and type of schooling).

I was given nine cities to consider in Spain, Italy, France, and Portugal. This list was more up my alley for sure. From there, I got more specific with my questions around schooling, different neighborhoods, and budget. It has been a fun exercise and one I will continue to do as I reflect on my values, needs, and desires.

🇪🇸 Spain: Valencia, Alicante, Málaga
🇵🇹 Portugal: Cascais, Faro (Algarve region)
🇫🇷 France: Nice, Montpellier
🇮🇹 Italy: Cagliari (Sardinia), Sicily (Palermo or Catania)

Not surprisingly, Valencia appeared. Again.

Valencia is an incredible option based on your criteria. It’s one of the most affordable coastal cities in Western Europe, with a fantastic balance of nature, culture, and modern amenities.

I’ll admit I was a bit disappointed that more places in Italy didn’t make the cut. I previously lived in Palermo for six weeks in 2020 (shoutout to the Sicilian family who hooked me up with their adorable villa near the beach for free), so fortunately I don’t need to visit to know that I wouldn’t enjoy living there full-time. I felt a bit uneasy there as a woman (you can only hear principessa so many times before you crack) and even had a stalker at one point.

Sardinia is tempting, and multiple people have suggested that I check out Cagliari, which I will, but I don’t think I want to live on an island. Always a nomad at heart, I’d prefer a place with easier access in and out.

I had a feeling why Rome, my favorite city EVER, wasn’t listed, but I asked, just to test AI’s logic, and this is what it said…

Rome isn't on the list because it doesn’t fully meet all of your criteria, especially in terms of affordability, air quality, and strong expat-friendly infrastructure compared to cities like Valencia, Málaga, and Alicante.

It also said “If history, culture, and an Italian lifestyle are priorities, Rome has no competition...” I must say I wholeheartedly agree with that statement. Rome is pure Italian magic bottled up in one swoon-worthy city of golden light. I was just there to celebrate a friend’s birthday and it will always have a special place in my heart. I just don’t know if basing myself there is the solution. The good news? Rome will always be there.

At the end of the day, am I going to make a decision based on artificial intelligence or the opinions of strangers, both solicited and not? No.

I am, however, going to take into account what matters to me most and filter everything through that lens. And I can’t wait to see how that feels.

If you have an expat friendly place you think I should check out, please share below. I’d love to hear from you. I’m in full research mode at the moment which, as anyone with wanderlust knows, is an exciting place to be.