How to live in Italy for 6 months

How do you do it, Cassandra?! Split your life between two of the most beautiful places in the world: NYC and Italy? It has always been a dream of mine!!

I get this question, almost daily.

I find many of you are so curious as to why, how, and my plan for living between two countries. 

Finally, I am sharing my thoughts and anwsers with you today. 

 ME - PHOTO CREDIT GOES TO PHILLIP H.

ME - PHOTO CREDIT GOES TO PHILLIP H.

 ME - PHOTO BY MARIA R. PHOTOGRAPHY

ME - PHOTO BY MARIA R. PHOTOGRAPHY


Ten years ago I used to ask this question to anyone I knew fulfilling this dream too.  

Since 2007, THIS was my life goal. I said, "I will live in  Italy."

Then having lived here for almost three years, I said "Nah, full time is too much. I will live between NYC/Brooklyn and Italy. Then following this goal I decided my ultimate goal was to spend more time on near by the Amalfi Coast region.  And so I finally did.


Why was this your life goal?

Living half the year abroad may sound like a dream to many, maybe an experience, or a way to change up their life, but to me it's much more.

Sounds deep right? I know, I think exactly the same! 

Why Italy? I find it interesting that it really has nothing to do with the beauty, architecture, history, or food of this amazing country.

Nor does it have to do with a love relationship or a work obligation I created this idea on a simple lifestyle goal I have had since I was in my teens.


A quick back story as to why Italy has meaning to me

Raised in a Sicilian American family, I grew up without any real appreciation for the wonderful privilege of Sunday dinners, afternoon's helping my grandparents in the back of the family pizzeria, or even a basic snack being affogato (gelato and espresso).

It was all so ordinary to me. Didn't everyone live this way?

I realized only after the untimely death of my father and grandfather how fortunate I was with this Italian lifestyle. I began to realize the impact it had on me as an individual and how much I missed this feeling. 

It inspired me to reconnect to my heritage on a different level not just through a yearly vacation.

It was never a question of ‘if’ but rather when?

How and when did you start planning?

Over the last few years, I slowly started to develop a loose plan.

It was never a question of 'if' but rather, when? Every job I had over these years had some association with this dream in mind and I knew I could use all my skills to make it to my ultimate goal: Six months in Brooklyn/NY and 6 months in Italy.

The very first step I took was developing a job that allowed me to do this. This is how my online Italian travel company Travel Italian Style was born! 

Then the next step, I stayed three months here, 4 months there, 5  months, then finally 6 months. 

Suddenly, it happened! I split my time and the way it worked out I was even able to  include a few months on the Amalfi Coast, just as I planned! 

At times I thought it would not work out. For example, just this past year during my planning, an apartment fell through and the only place I was presented was in Naples.

I was very hesitant at first, but actually it was the best thing that could of ever happen! Besides loving the city, I got over huge emotional and fear barrier. I was even able to expand my network of vendors for clients. In the end I feel pretty blessed this happened. 

Life, you gotta love it! 

*Advice: Make a plan but be open to what is presented to you! 

 MY PASSPORTS AND CAFE IN AMALFI COAST CERAMICS - PHOTO BY TRAVEL ITALIAN STYLE

MY PASSPORTS AND CAFE IN AMALFI COAST CERAMICS - PHOTO BY TRAVEL ITALIAN STYLE


Is it lonely?

 ME - PHOTO BY MARIA R. PHOTOGRAPHY

ME - PHOTO BY MARIA R. PHOTOGRAPHY

Sure speaking another language daily, living alone, traveling with a 30 kilo bag for 6 months, or not being able to find a basic toiletry (haha), is scary and emotional at times.

However, for me, it is scarier to stay in an office job.

It would be even more emotional if I had to spend a year without experiencing the southern Italian sea, engaging in a conversation with Italians, riding on the back of a scooter with the wind on my face, enjoying a Nastro Azzuro beer or Spritz as the sunset, or enjoying a parmesan focaccia with my friends in Florence. 

These are the simple moments but the ones that mean the most.

I know how lucky I am and there is not a moment that I forget this. Even on my toughest days I do not take for granted that I get to incorporate these experiences into my life. 

Advice: Be comfortable being alone. Remember you will be in a foreign country. This takes adjusting. Just be kind and focus on the everyday beautiful experiences that brought you there in the first place. 


Blah, blah, your story is cute but can you just tell how you got a visa to live abroad?

I have a dual-citizenship through my nonna. To be eligible your grandparents should not have renounced their citizenship for Italy before your parents were born. Lucky for me, my nonna lived in the USA with a green card, so I was in the clear.  

Not so lucky for me, she changed her name, illegally. With this being said it took me 7 years and thousands of dollars to obtain my Italian citizenship!  After being turned down about 5 times, one day I suddenly got a letter in the mail stating my birth certificate was now in the town of Canicatti, Italy.

And there you have it. One year later I had an Italian passport in hand.

Call it a miracle, call it luck, I call it my dad and nonno in heaven just saying, please god do something about this, we are tired of hearing Cassandra praying for this Italian passport . ;)

Grazie babbo!

By the way, just to add to the drama, the day I received notice of my Italian Citizenship was the one time in my life that I cried out of happiness. 

Advice: Later in this post I also share a link with Italian Visa 'ideas.' In the meantime, I recommend heading to your local Italian consulate website to find out if this can work for you too! Here is the NYC consulate. Be ready to invest a bit of time and money into the process.  If you need help finding paperwork my company provides services through genealogist  to assist. Feel free to contact us here. 


But how do you make it work financially?

I am not a magician, I am not rich, and I not sponsored by anyone or anything. As a single entrepreneur, the best way I know how to live is to make it work on my own. 

I am VERY lucky and grateful that through my network of friends and my job, I can normally find an apartment in NY and sometimes even in Italy that works for my budget.

If you know someone, DO NOT BE AFARID TO ASK FOR HELP! In the beginning I really did not want to bother anyone but really, most people do not mind connecting you with someone that could be of assistance, so why not try?

Then I spend some time traveling in between apartment living.

Right now I also sacrifice. If I want a nice apartment than I spend more time eating meals at home. If I know I have to tour and dine out in a region for research then I stay in a lower budget B + B.

I hope one day that I can afford my own apartment in both cities. But building and empire and a life at the same time ain't always easy folks. For now I am ok with taking it one day at a time or as the Italian's say piano, piano (slow, slow).

Personal Advice: Save money or find a way to make money while traveling. Be creative and be open to taking on a few jobs if need be. 

Work Advice: Do your research on Italian laws and taxes BEFORE moving abroad. This comes for both being an entrepreneur or someone working on a visa. The best way to do this is hire an accountant or a lawyer.


Any suggestions on where to move in Italy?

I remember in the past, I always imagined living in the Tuscan countryside in a house that would allow me to roll around in lavender and run through sunflower fields. Seriously this image is not THAT exaggerated, haha! I pictured a beautiful dinner table set up in the vineyards with local olive oil, fresh  bread, and pasta everyday.

 TUSCANY - PHOTO BY TRAVEL ITALIAN STYLE 

TUSCANY - PHOTO BY TRAVEL ITALIAN STYLE 

But then one day I woke up and said:  "umm I don't want to be stuck on a one-way road for 20 minutes just to get toilet paper and where would I get a morning pastry if I was alone in the countryside and there is no way I could eat pasta everyday." 

This idea is still dreamy and luckily with my job I can make that image come to live every once for myself and others. However, I understand I had to be a bit more realistic when it comes to living in a place everyday.

I say stick to what you know! If you grew up on a farm then maybe a farm or the countryside is a great place to start.

If you grew up in a city, start in a city! For me a city was a great place to start. I appreciate the walkable to what I need. I also love the idea of heading to the cafe every morning, which is a bit easier in a city or actual town.

Also, I recommend spending some time visiting a place, not just stopping during your vacation and making the decision.

I know some may disagree and I understand that it's possible to get that 'feeling of home' right away. But just like a relationship, if you let it go and it comes back to you then it is meant to be, so why not give it a few visits before leaping into the big move. If this is the place for you, it will be there waiting for you with open arms when the time is right. 

Advice: Being spontaneous is cool but I would not recommend it for this situation. Six months is a long time and you want to be comfortable as possible in a practical situation that works for you! 


What about making friends?

Currently, my only friends in the region are a few industry buddies I have met along the way.  

So basically that leaves me doing the same thing I do everywhere else in the world, working. Sounds depressing, right? Yea sometimes it is lame but overall, for me this is fine because I am hustling (yes this is Gary Vee inspired).

The relationships that I allow in my life are with the people that create meaning. I have never really been the type of person to surround myself with just anyone. I am not saying I do not enjoy a fun night out or meeting new people because I do.

However, I appreciate spending time with friends that live a similar life, that inspire me, and ones that dream like me! I love meeting others but if I am giving up half my life to live here in a foreign country, I want it to be complete with good people. I try to connect with locals in the region through social media and hope for the best. 

On a side note,  I believe you attract in your life who you need. Usually this means that person needs you too. So just keep that mind. If you want a meaningful life then you will want meaningful relationships too. 

Advice: Surround yourself with those you can learn and grow from/with no matter where you are in the world! 

 SORRENTO PORT - PHOTO BY TRAVEL ITALIAN STYLE

SORRENTO PORT - PHOTO BY TRAVEL ITALIAN STYLE


If Italy is so great, why go back to NYC?

Well first all, FOR ME, I have never been a fan of Italy in the winter months. 
 
However, the real reason is more because I need New York too, I am a New Yorker. Born and raised. 
 

 Oculus, NYC - PHOTO BY TRAVEL ITALIAN STYLE

Oculus, NYC - PHOTO BY TRAVEL ITALIAN STYLE

Besides my family and friends, I can't imagine a life where I would have to miss out on the amazing nighttime NYC skyline or being able to shop at Target. I mean really where else can you pick up your Starbucks, buy lipstick and house cleaner all in one place?!

I love the energy, my friends, my network.

I love that NYC attracts amazing interesting people from around the world and brings out the best in people. It is as if we all get a fire lit under our butt's and are brought back to life (even for just a split second) just by walking past the Empire State building.

I don't know any other city in the world that can do that to you! 

I also grew up with that excitement of visiting Brooklyn and NYC's Italian locations. How could I go a whole year again without going to Villa Abata or enjoying a slice of pizza from Spumoni Gardens? I am sorry but this is physically not possible. ;)

Advice: Ask yourself, 'where else do I feel most alive in the world?' Then make sure you spend time in that place too! 


Just out of Curiosity, Where do you feel most at home?

I actually feel about the same in both places.

I have talked about this before on my Instagram. I do not feel 100% Italian but I also do not feel 100% New Yorkese.

All I know is when I am in both places, I try as much as I can to make it my home. 

I basically just do the standard stuff wherever I am in the world. Some examples would be finding a local/daily coffee shop, a route to run in the morning, and just a basic routine to just try to live my life normally.

Physically speaking I felt very sad with my grandmother's passing and not being able to attend the funeral. I also miss seeing my little nephews grow up. But thank god for Facetime and for pray. You learn no one is really that far away in the end.

So, I guess the response to this, I feel more at home where I am at the moment.

Advice: Start feeling comfortable with the idea of home being in your heart (no matter how cliche that sounds).


Where you are is who you are. The further inside you the place moves, the more your identity is intertwined with it. Never casual, the choice of place is the choice of something you crave.”
― Frances Mayes, Under the Tuscan Sun



Can you just give me some advice already. how I can do this already? my dream is to live 6 months in Italy!!

 CAFE IN FIRENZE - PHOTO BY TRAVEL ITALIAN STYLE

CAFE IN FIRENZE - PHOTO BY TRAVEL ITALIAN STYLE

Then go friggen do it! It is as simple as that! 

I actually have no idea the right steps that YOU need to take. I told you this already a few times in this article! ;) 

However, the advice I can give is to start asking yourself these few questions:

Do you have the mind strength and resources to REALLY give up half your life to live abroad?

Do you have obligations that tie you to one place?

What are your priorities in life right now? 

If you have a family, can you afford to live on the road or live and work from home?

Can you obtain dual citizenship? Or can you receive a visa that allows you to travel freely (scratch the student visa, the chances of this working out is 1 out of 100000000). However, this website seems to have some creative visa ideas.

 How bad do you want this? 

Would it be worth sitting alone most nights and having less than 5 real friends near by?

Are you comfortable with going out to dinner alone?

Are you ok with speaking another language every single day for 6 months straight with no breaks?

If you are thinking to start a business here, are you prepared to do business with Italians? And yes this deserves it's own blog post - HA!

Are you prepared to go through many waves of emotions?

These are just a few of the questions I used to ask myself. And when I finally said, "yea I think I can handle all of this," then I made the move.

Advice: If you had the same reaction as I did to these questions, then make it happen.


 NORTHERN ITALY DAY TIME SPRITZ - PHOTO BY TRAVEL ITALIAN STYLE

NORTHERN ITALY DAY TIME SPRITZ - PHOTO BY TRAVEL ITALIAN STYLE

one final recap of the steps to making your dream of living between two countries come to life

1. Do your research on how to get the right travel permissions.

DO NOT SKIP THIS STEP! I really do not recommend trying to live illegally during this process.

2. Pick a place that makes you feel at home.

3. Make a plan to financially support yourself on the road.

4. Buy a plane ticket.

5. Start preparing your mind and body for this beautiful adventure. 


Any inspiring words to get me motivated?

Just do it and don't give up.

Learn to work, live, and embrace being Italian. Then you will BE Italian. Manifest and imagine you are already there and then I believe you will have all you need to succeed.

My life could be easier but it could be just average too. I am not sure what my destiny is but I try not to think about it too much, I just try to live it as much as possible.

 NAPLES BY SEA - PHOTO BY TRAVEL ITALIAN STYLE 

NAPLES BY SEA - PHOTO BY TRAVEL ITALIAN STYLE 

Is my life purpose to be an Italian travel planner? I have no idea!

It may just be a stepping stone, something to get me here, to keep me here until I find my true purpose. So for now I will keep doing that.

Until the universe leads me to my next path.

Is it easy? Heck NO! However, I do only what I know. I try my best everyday to stay honest, authentic, and hardworking. I make many mistakes but I always get back up and try again to try and make the situation better. This is all we can do when living a meaningful life. :) 

 

 

Final Advice: Can you relate to this article? If so vai (go)! And if this is really your dream the remember this great advice I heard once, "you can retreat, but NEVER surrender."

 

I will be sending you lot of love and light for your journey from the mountains of Sorrento and the skyscrapers of NYC. <3 And please feel free to introduce yourself to me below or via email at info@travelitalianstyle.com, I would love to meet you and welcome you to the club. ;)!

 

www.travelitalianstyle.com - Custom Travel Planning for Italy - info@travelitalianstyle.com

“I don’t want my life to imitate art, I want my life to be art”
— Carrie Fisher

Meet the author

 CASSANDRA SPEAKING AT TEDX DHBW MANNHEIM

CASSANDRA SPEAKING AT TEDX DHBW MANNHEIM

Cassandra Santoro is the CEO and Founder of Travel Italian Style.

As a personal trip planner Cassandra is an expert in Italian travel with a focus on authentic and inspiring experiences. She also leads motivational talks and can most recently be found TEDxDHBW Mannheim.

Cassandra is currently writing her first series of short stories and lives between NY & Italy. Follow her adventures in Italy on Instagram.