Settling Into Italy (and Sorting Out My Visa)

Published on 10 June 2026 at 11:48

I feel like I have gone through every emotion possible these past two weeks in Italy. I knew it would be an adjustment, but I didn't realize just how hard it would be or how guilty I'd feel for being overwhelmed and homesick.

Yes, I am grateful and happy that I made this decision, but that doesn't completely quiet the voice in my head that reminds me how easy and comfortable my life is back home. I think moving to a different country, even temporarily, makes you think about your own country in a way you never have before. You start comparing everything.

I love experiencing new places and new ways of life, but when things get tough it's hard not to want to book the next flight home and hug my friends and family.

Being at the winery is truly breathtaking. The vineyard I am living on is absolutely beautiful, but without the people I live with, I think I would be completely lost. It's been eight days at the house, and I can honestly say I couldn't have done it without them.

We're about an hour's walk from the nearest town, which is very small, but only a six-minute drive away. Since the Polish couple I live with have a car, we’ve gone out together a couple of times, along with our other roommate from Holland. Grocery shopping, doing laundry, grabbing a drink, all the little things that suddenly feel a lot bigger when you're in a new country. I couldn't have asked for kinder or more welcoming people to share this experience with.

So far I've worked in the tasting rooms helping set up, pour wine, serve and prepare food, and clean up. I've also spent some time working out in the vineyard, which is very hard work and leaves a lot of room for reflection. I wanted to experience every aspect of winery life, and I'm excited to learn even more over the next five months.

Starting any new job comes with a learning curve, and adjusting to a completely different work culture has definitely had its moments. Coming from a government office job, there have been a few communication differences that have caught me off guard, but that’s part of the experience. I’m trying my best to adjust and take a more easy-going approach like my friend Sofia from Holland.

Lastly, for anyone curious about the Working Holiday Visa process in Italy, here's a rundown of my attempt to get my residence permit (permesso di soggiorno) so far:

• Arrived in Italy and went to a Questura in Rome. They told me I needed a Dichiarazione di Presenza and sent me to a different Questura.

• Went to the second Questura in Rome. After explaining that I had a Working Holiday Visa and would be living in Tuscany, they told me I needed a Cessione di Fabbricato and that it had to be completed within eight days of arrival.

• Travelled to Florence. Since it was Sunday, everything was closed.

• Monday morning: Post Office. Picked up the residence permit application kit and was told to visit a CAF office for help filling it out.

• CAF office: closed.

• Watched YouTube tutorials and realized I first needed an Italian tax code (Codice Fiscale).

• Went to the tax office and got my Codice Fiscale.

• Filled out the permit application kit and returned to the Post Office.

• At the Post Office, I was told that because I have a Working Holiday Visa, I couldn't actually submit the kit there. Instead, I needed to complete a different red-and-white form, pay about €70, and bring the receipt to my future appointment. I was also told I needed to go directly to the Questura to book that appointment.

• Went to the Questura in Florence. They told me I couldn't book an appointment there and needed to go through a CAF office.

• Explained that the Post Office had literally just sent me there.

• The officer basically shrugged and said there was nothing he could do.

• Left because they were closing.

• Returned later because the posted hours said they would reopen.

• They did not reopen.

• Came back the next day.

• Also closed.

• At this point I was starting to think opening hours in Italy are more of a suggestion than a rule.

• The winery owner picked me up, and I spent the next week unpacking, working, and learning the lay of the land in this beautiful rural area between Florence and Siena.

• After a week, I headed back to Florence. I walked 55 minutes to the bus stop, took a one-hour bus ride, and finally arrived.

• I waited in a line of about 50 people so I could explain my situation for what felt like the hundredth time, only to be told to come back at 11:00 a.m. It was 9:00 a.m.

• While waiting, I copied paperwork, printed documents, grabbed a coffee, and mentally prepared myself to explain my visa situation yet again.

• Returned at 11:00 and waited another 30 minutes, only to be told I was in the wrong place.

• Thankfully, a woman in line who spoke both Italian and English took pity on me and explained where I actually needed to go. She typed the address into my phone and sent me on my way.

• I arrived at the next office only to find the entrance blocked off. I went in anyway and asked two very kind officers for help.

• They directed me to yet another office.

• I cried on the street.

• At the next office, I met two officers who were incredibly kind. One spoke fairly good English and spent nearly two hours helping me.

• For the first time, someone really seemed determined to figure out what I actually needed to do.

• He called multiple offices, asked questions, and tried to piece together the puzzle I was trying to solve. I had been following bits of information I found on Reddit, but was being told something different at every step.

• Eventually, he gave me an email address and explained that I needed to register for a certified email account, request an appointment, and send all my information through that system.

• I have now done that and received confirmation that my email was sent.

• I haven't received a response yet, but for the first time in a while, I feel hopeful.

So yes, the last couple of weeks have involved being sent in circles between police stations, post offices, tax offices, and offices that seem to exist only when they feel like it.

I've definitely cried more than once out of frustration and confusion, but I'm trying to take it one day at a time.

Despite all the bureaucracy-induced tears, the countryside is beautiful, the people have been kind, and every day feels a little less overwhelming than the one before.

I'm slowly settling into Italy.

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Comments

Morgan Sheppard
2 months ago

What a journey you have been on already! Sending my energy your way so the next few weeks get better and better, oxoo

Tia
2 months ago

You are so capable even in the hardest times!
Miss you and can’t wait to read the update post when the visa comes through. Thankful for kind strangers.

Brad Stroud
2 months ago

A tad bit overwhelming to say the least!! So happy you found a few good locals to help you through your application period!! Keep a smile on your face and enjoy the best and forget the worst.

Erin Sheppard
2 months ago

Sending ginormous squishy hugs from home!! We are super proud of you for taking this giant leap of faith and know you will come out on top!! Xoxoxo

Michelle
2 months ago

WOW. What a journey. I’m sorry for laughing while reading this hehe <3 loving the blog posts

Breanne
2 months ago

The amount of pride I have reading this is astounding. Your courage, tenacity and sheer determination is going to inspire so many people. Keep showing up, doing the hard things, and building a beautiful life. All the love from back home.

Glenda Newbatt
a month ago

I hope you are incredibly proud of yourself, sweet girl, for your determination in living out one of your dreams. I know we are all proud of you and miss you lots. 🩷

Ivy Wilson
a month ago

My sweet girl this is your dream, follow it through as I know you will, hard times are part of learning and preparing you for all the good times to come.
I am so very proud of you. You are following your dream, I miss you terribly sending you lots of hugs.
Now wipe those tears chin up and keep doing what you do best.
Love you lots

Cami
a month ago

A desperately long journey that I’m sure will turn out beautiful and completely fulfilling! Sending you energy and strength, you got this! It wouldn’t be the trip of a lifetime without a few hurdles (also considering nothing visa-related comes easy!) but I know you’ll figure it out eventually xoxoxo

Maisie
a month ago

All the emotions! Sending you the biggest hug!! You’ve got this, you’re so strong and it will all be so worth it. We’re cheering you on! I’m so proud of you, what an adventure ❤️

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