Every time I came back from a trip to Italy (which has been every year for the past three years) my friends and family would tell me, “You’ll live there one day!”, a statement that I vehemently denied.

Why, you ask, when I obviously love the culture, the food, the history, the people?

Living somewhere is very different from visiting there.  When you visit, you don’t have to deal with daily life, which is going to get monotonous any where you are.  And let’s be honest, even though I dream at night of small villages where you go to the market each day and visit the baker, butcher and candlestick maker individually, I love my ritual trips to Target and Trader Joe’s.  American life can be very convenient, particularly compared with some of the stories you hear about the Italian bureaucracy (having to take a half day off of work just to go to the bank? No, thank you!).

Plus, let’s face it: young to middle-aged single women moving to Italy has become a little bit of a cliché.  And I never want to be cliché.


I recently left my job.  I had been there for twelve years – since I was 20 years old – and though I loved it, I found myself needing a change.  I’m no longer interested in being expected to answer my phone 24 / 7, in going over a marketing plan at 11pm on a Wednesday that could easily be discussed at 8am the next morning.  I like to work hard, but at this point in my life I need a job that also let’s me have a life.  And let’s face it, it’s kinda my fault, too.  I tend to be a bit of a work-a-holic, but I work in an industry, in a country, that encourages me to be.

What I need now is perspective and distance.

And that’s why I’ve decided to make a (temporary) move to Milan.  From March to May I’ll rent a series of apartments in Italy’s most international city with two goals in mind:

1) Do I actually like living in Italy?
2) Can I find a way to pay my bills?

My Italian dual citizenship should be approved sometime this spring, which will make it easier to find a job than if I had to have someone sponsor a work permit.  But as everyone’s told me, the economy in Italy isn’t experiencing its finest hour, so I’m anticipating a challenge.

After I decided to try living in Italy, there were a few things to consider:

1) What? What will I do while I’m there? How much of my time should be “work” and how much “vacation”?

2) Where? Which city should I go to?

3) When? How long will I go for? When should I leave?

4) How? Where will I live? What will I bring?

#1: What?

The idea of being in Europe and able to flit to different countries and cultures for a long weekend excites the shit out of me.  But initially, I know I need to focus on figuring out if I enjoy everyday life in Italy, something I won’t learn if I just use my temporary home as a travel base.  So, limit the travel to one long weekend and maybe one or two day trips each month.

Other than figuring out if I like the daily lifestyle, I also need to figure out if I’d be able to pay my bills.  Before I leave, I’ve started networking and reaching out to people through LinkedIn, asking about meeting once I’m there and sharing my resume.  I’m fortunate to have unique skills and career experience, which I’m hoping will help me network within my industry.  I’m not opposed, though, to simply teaching English (I received my certification to do so earlier this year) or working in a bakery – as long as I can earn enough to live.  Those sorts of jobs, though, I can’t really look for until I have my citizenship approved (there’s nothing special about me that would make them wait to hire me in those areas).  Pre-citizenship, I’ll network within the industry I’ve built a career in and see if I have confidence that I’d be able to find work once I have it.  It’s a little shaky, I know, but it’s all I can do at the moment.

I also want to explore the city and take some time to write, read for pleasure, cook new recipes and take care of myself.  You know – those things we always say we’re going to do but never make time for during the chaos of normal life.

#2: Where?

I’ve never been to Milan, so you may be wondering how and why I decided to spend my three month “trial period” there.  It just seemed logical, really.

For starters, my industry (entertainment) is based there, increasing my ability to network.  Additionally, Milan is home to a lot (if not most) of Italy’s international industries, making it a logical place to go for a native English-speaker.  Because a lot of industries there need to operate in English, there’s not only a demand for English-speaking workers but also for Business English teachers.  Milan’s need for English-speaking workers also means that it has a large ex-pat community and a varied restaurant & cultural scene.

One other thing Milan has going for it is its location: 45 minutes from the border with Switzerland, just a hop, skip and jump away from the rest of Europe.  For someone who revels in visiting new places and experiencing new cultures, this is a biggie.  I know I said I wasn’t going to travel much in the first three months, but if I am able to find a job and decide to make the move (somewhat) permanent, it will be easy to travel to other countries for a long weekend (or longer).

Don’t get me wrong, though – I plan to apply everywhere.  Rome, Perugia, Spoleto, Florence, Vicenza, Venice – any interviews I get will just be a train ride away.

#3: When?

I had my appointment at the Los Angeles Italian Consulate to file for dual citizenship on November 3rd (read the series of posts HERE).  At that time they told me that my application should be approved in 6-8 months, which would mean sometime between May 3rd – July 3rd.

Well, I had already quit my job (the timing had been right) so I didn’t want to wait that long, particularly because I wasn’t sure if I was actually going to want to live in Italy after my 3-month experiment.  I could go for 90 days on a tourist visa, so I decided to leave on March 4th and stay for 89 days, coming back to the US on June 2nd.  If I didn’t have an approved citizenship application by that point, it would be imminent and I could (potentially) come back to the States to organize my move and then return to Italy within four weeks, ready to work.

#4: How?

I’ve never used the service before, but in order to “test out” neighborhoods I decided to rent three different apartments – one each month – on AirBnB.com.  I like how AirBnB is set up because even though you pay immediately, they hold your money in a sort of “escrow” account and only give it to the proprietor of the apartment 24 hours after you “check in” and confirm that the apartment is as was advertised and that you will be staying there.  Therefore, there’s no reason for anyone to try to scam you because as soon as you got to the apartment and found out it wasn’t what you bargained for (or got to the city to find out the apartment didn’t exist), you tell AirBnB and they don’t give the host your money.  If that happens, they’ll help you find another available apartment within your budget.

I’ll be there during the Spring when it goes from chilly and rainy to the beginnings of warmth, so I’ll need to be able to layer.  I’ll also need clothes for work, for an evening out, for hiking, for the gym and a spattering of other activities.  And don’t get me started with shoes – I’m bringing about six pair (including walking boots, rain boots, dress shoes and athletic shoes), which I think is pretty good considering the range of activities and weather I’ll have to be prepared for, but the space it takes up in my suitcase makes me ill.  I’m bringing one two-suiter of clothes as well as one large, roller suitcase with shoes, gym clothes and miscellaneous things for the apartments (Apple TV, for instance).  I’ll also bringing a fairly large first-aid kit, as Italian medicines aren’t the same as American over-the-counter meds and, if I happen to get sick, the meds I’m familiar with may be my best bet.

There’ve been a lot of other things to think about – medical and car insurance, what to do with my car (I sold all of my furniture), an Italian CV (resume), new business cards, cell phone, money options, how to network (both personally and professionally)… to be honest it can seem a little overwhelming at times.

Now that the time is almost here, though, I feel ready.  Everything that I know of to prepare for, I’ve prepared for, and I can’t worry about what I don’t know.  I’m sure there will be a lot of surprises once I get over there, a lot of things to get used to, but I’m looking forward to them.  And I’m looking forward to telling you all about them, as the happen.

I’m merging my old Instagram and Twitter accounts with my personal ones, so you can follow my ex-pat adventures at:

Twitter @JustToJess

Instagram @JustToJess

And, as usual, I’ll be posting to:

The Official Site – OneDayInItaly.com







About the author



Italian Travel Planner and Italian Culture Enthusiast

4 Responses

  1. criatina campiolo klinzman

    Hi . I have dual citizenship too (brasilian/italian maried withan american guy) . I know how hard is to get the citizenship ( its italy right?) so if uhave trouble or something did not work out I know a place in Campania people who has all the documents stay (5 euros day B&B ) and the major help you to have the citizenship really fast (he needs to improve the population so..) I have a daughter living in Milano .married with an italian guy and they are into hotel business .. Good luck !!

    • Jess

      Thank you, Criatina! My citizenship documents have actually already been reviewed and the final approval paperwork should be here within a month or two. Thank you for your kind words! :)

  2. Lisa

    In bocca al lupo. I’ve done the same thing in Sorrento. I’ve got lots of tips, especially the “TV” thing. Email me if you want some survival skills :)

    • Jess

      Crepi, Lisa! You mean watching American TV in Italy? I think I’ve figured that one out (fingers crossed – haha) :) Any tips you have would be welcome! I love Sorrento – beata te!!


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