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Hey, there!

Welcome to Road 142 where I, Cara Crowley, a stylist and content creator chat and share about fresh + easy ideas for everyday life while exploring the backroads and farms of my beloved Northern California. I’m so happy you’re here!

A Month In Italy

A Month In Italy


It all started when I was on my phone last week playing one of my favorite games --looking up flights all over the world and playing with dates and times until I find an amazing price. This is a risky little game of Russian roulette because 9 times out of 10, I won’t find a good price but every once in a while I come up with a round trip ticket to Rome for less than $500, with a seat actually inside the plane, that I just can’t pass up. I looked at the details of the trip because I MUST have missed something; surely there had to be multiple flight changes, a day layover in a random airport or leaving/arriving at awful times. I looked at all the details over and over and everything seemed very doable – flying out of SFO, a quick layover in Madrid and then arriving in Rome. 

 I causally mentioned it to my mom when we were talking that evening and she reminded me that she had a bunch of airline miles that she had offered my siblings and I to use before they expired. I said, “oh that’s right but I can’t go” and her response was “why?” That started the search for flights in the on the airline miles website and surprisingly there were two days in May and June that were 30k miles each, the lowest that American Airlines offers for international flights. However, the two days were a month apart. And while there were enough miles for me to come home on a more expensive flight and stay for a shorter duration, there was something so alluring about being in Italy for a month but who does that?!. Again, I responded that I couldn’t be gone for a month. My mom shrugged her shoulders and again said “why not?” She was right, there were no really good reasons that I couldn’t, everything could be worked around by scheduling and/or done remotely. So, that is how I booked a ticket for a month long stay in Italy.

Since booking my flight and apartment, there have been a lot of curious questions about my stay so I thought it would be fun to answer a few of them here:

Have I been to Italy before and do I know Italian?

Yes, I have spent a total of about three weeks there. I adore Italy and honestly live my best life there – who doesn’t?! The Italians just get it when it comes to the art of living. I don’t speak Italian here in the states but pick up conversational Italian very quickly when I’m there and immersed in the culture.  I have also found that most people in Italy speak English. I don’t rely on it but it is helpful and I am always humbled by the grace that is extended to me when someone offers to switch from speaking Italian to English to make me more comfortable. I do and have always assumed the idea that if I’m in a foreign country, it’s my responsibility to speak the language of the country I’m in so it really touches me when strangers are kind enough to speak my native language.   

Where are you staying?

I booked a furnished apartment in a lovely residential neighborhood in Florence, where I will be staying the majority of the time. Florence is such a great city to stay in and take day or overnight trips to other parts of the country.

Don’t you have to work?

 Absolutely! I have to work, just like everyone else. A few years ago, I dramatically changed the way I work and switched from in-person client work to mostly working remotely. I do need to have in person client meetings from time to time but they aren’t anything that I can’t plan around for that month. Administratively, we already work remotely. Amy, my amazing administrative team member, actually lives in Montana. Funny enough, we have never met in person! The photographers that I work with are generally remote, as well. I will be taking my laptop, camera and obviously my phone with me and can produce work while I’m there. The only biggest hurdle to work around is the time difference but personally as a night owl, it works for me. It’s an 8 hour time difference which means I can experience Florence during the day and then work in the evenings when it is work hours here.

For those of you who may not know what I do for work – I work as a digital content creator and work with creative agencies and PR companies.


How can I afford it? 

 From spending time in Florence before, I know my cost of living is about equal to what it is at home (even taking into account that the Euro is stronger than the American dollar) so my day-to-day expenses are something that I already manage. My flight was $78 along with the miles and the biggest expense is the apartment, which is an expense but pretty reasonable since I chose an apartment about a mile from the center of Florence in a residential neighborhood. There will be other costs to manage there like train and/or airline tickets to travel to other countries but after doing a little research and from experience, I found that it really isn’t that expensive. My ability to make this happen is also due to how I live my life at home. My expenses are very low in my everyday life to allow for things like this to happen and to be able to take advantage of these opportunities. I don’t have a mortgage or household repair expenses (I sold my house last year), I drive a seven year old Honda that is paid off so I don’t have a car payment, I have nice clothes, and even a few designer labels in the mix, but don’t have my money tied up in possessions/clothes and I while I live nicely, I don’t live a crazy expensive life.

Am I nervous?

Of course. I am not naturally fearless, in fact I live with severe anxiety that at times can be paralyzing but I am learning to live with my anxiety and instead of waiting for it “to be over”, I am embracing it and trying to go with the flow. I think of it like a dance; some days it leads and some days, I do. One of the ways that I can get the upper hand on it though, is to do things that make my soul happy and travel is one of those things. This trip has many elements that make my anxiety tick up a few notches though. This stay is less a vacation and more living there, in fact it is a trial run to see if I like living there because one day I would like to spend a couple months there a year, splitting my time between Northern California and Tuscany. There will be bus routes to learn, friend making to be had, and grocery store shopping in a foreign language along with nuanced customs to learn, to name a few things. But just as here in the states, I’ll take it one step at a time and I’m sure I’ll be just fine.

 I’m also nervous to be on my own for the month. This feels odd to say because I’m an introvert and naturally do well by myself for extended periods of time but a month feels a little long especially in a different country where nothing is familiar. My goal is to make a friend or two when I’m there and to give me the motivation to make friends, my biggest goal while I’m there it to host a small dinner party at the end. I am looking forward to shopping local markets for ingredients, cooking using the metric system and inviting a couple of new friends around for dinner.

Will I come home?

 Ha. This is my mom’s question every time she drops me off at the airport to which I generally answer with a dimpled smile and shrugged shoulders that usually indicates that I’ve got something up my sleeve. But yes, I do have return flight booked and will return home as the Italian government would like me to.


UPDATE: You can find out how my trip went, if I ever came home ;) and photos in my Instagram saved highlighted stories here

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