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Inspired by: Cassandra of Travel Italian Style

Inspired by: Cassandra of Travel Italian Style



I came across Cassandra while doing what I always do in my spare time (and when I’m procrastinating):  instagram stalking Italy. I instantly became immersed in her feed and increasingly interested in her business as I continued to scroll down. Cassandra is the CEO and Founder of Travel Italian Style. As a personal trip planner and luxury small group tour operator, she is an expert in slow-travel and authentic and inspiring experiences throughout Italy.

From wandering the streets of historic medieval towns like Lecce, Matera, and Polignano a Mare, to taking in the pristine waters of Southern Italy while admiring it’s unique mix of Baroque architecture and sandy beaches; Travel Italian Style offers the most authentic way to explore Italy. Perfect for those who, like myself, enjoy traveling off the beaten path and consciously want to avoid the tourist traps and crowds. Imagine participating in olive harvests, attending private local music gatherings, learning about the amazing slow food cuisine, making pasta from scratch and of course wine and cheese tastings galore. From Venice to Rome, Florence to the Amalfi Coast and many stops in between, Cassandra has spent the last 10 years connecting with locals all over Italy whom act as guides on her tours, showing her guests the hidden gems of Italy while teaching them their crafts and traditions; truly providing a one of a kind experience. TIS offers different packages; tours of Southern Italy, a wellness and water retreat on the beautiful islands of Sardinia, and custom packages all over Italy for solo travelers, couples, and groups of all sizes. A package I found particularly unique and interesting is the “Customized Italian Heritage Vacations,” where you are connected with a professional genealogist and guided through the same streets your ancestors walked while discovering the town where your family lived and worked. This is something I have always dreamed of myself, being half Italian!

As much as what Cassandra’s business has to offer and has me yearning to jump on a plane and attend a tour, it was Cassandra herself and the story behind how she started Travel Italian Style that really drew me in. Knowing only a snippet of how she got to where she is now from what she shares on her instagram feed, I felt compelled to reach out to see if she would be open to sharing more of her adventure to Italy. Luckily she was game, and it has proven to be another example of how social media can be used to connect you with truly wonderful people doing inspiring things. Read my interview with Cassandra below to learn about her journey to Travel Italian Style; how she flourished into starting her own business, leading motivational talks (she can most recently be found at TEDx DHB Mannheim!), writing her first book and living the inspired life of her dreams between NY & Italy.

Caution: it may inspire wanderlust, vivid dreams of Italy, sudden urges to book a flight and encouragement to follow your bliss. 


Tell me about your journey to starting Travel Italian Style.

Travel Italian Style started by following my intuition. As a child I never really had a desire to travel abroad because really I had an Italian life every Sunday at my grandparents.

After the passing of my father in 2002, I began to have a sudden urge to explore and learn more about life outside of NY, especially Italy. After a few weeks of searching, a pop-up came up on my screen, which led me to an internship via a company called Global Experiences, which ultimately led me to intern as a tour leader for a travel company called Florence For Fun.

I took a chance, got on the plane, and my entire life changed. From this point on I was back and forth between Italy and New York working in tourism, hospitality, and events.

In 2015 as I was working in the NY wine industry, I began to realize that more guests were curious about my life in Italy than the wine, it seemed they wanted some assistance on their trips to Italia as well.

So I found myself helping planning their trips for no charge, as a fun outlet from my everyday work, but the moment I realized I was doing more than my full time job, I started to develop Travel Italian Style. Ultimately it was being fired from my job that gave me the strength to go full time into the business, I had no choice, and I wanted not only to survive, but to excel. And so here I am!

Did you have moments of doubt when starting TIS? How did you overcome these doubts?

I was more full of doubt than anything. It was the fear, the advice around me, the pressure to do something easier, such as become a travel agent for an already established corporation or go back to work full time. 

But I knew if I worked hard, I could rise above and that is what I did. I decided to dedicate every moment to social media, networking, and learning. I started to reach out to influencers, attend business and travel events and even joined entrepreneur groups that were outside of travel, just to gain knowledge and support. This is what helped me get through the tough times!

Why Italy? What was it that initially drew you to Italy?

It was my heritage and also the idea of appreciating the simplicity of life and even the dedication to one another. Italian’s know how life should be lived from food, to spending free time, to friendships.

Even after all these years my Italian friends remind me of the mentality I must incorporate into my life and that is “Cassandra just relax, you know it will all be ok.”

What are your favorite cities in Italy and why?

My first visit abroad was to Florence and now has become my home base for half the year when I am not in NY. So of course this city always has a special place in my heart. 

My other favorites could easily be: Positano, Naples, Palermo (Sicily), Ragusa (Sicily), and I have a feeling after our 2017 Tour, Alghero in Sardinia

You live between NYC and Italy, are there certain times of year you spend in each place? Or is it sporadic?

I try to be in Italy during the high season (June-October) so I can easily speak with my clients traveling abroad and my business partners. It is much easier being on the same time zone for those who have last minute questions or just want to send me photos of their trips (which happens often and I love it)! Plus, I love autumn in Italy!

It works out perfect because I love being in NY for the holidays and January/February when the season is a bit slow. It’s a great time to reconnect with fellow industry professionals who will pass through Manhattan during this period.

What is it like being a woman entrepreneur in Italy? Is it accepted there like it is in America?

Entrepreneurship for women has grown quite a bit in Italy. I have a wonderful network of a variety of business owners throughout the country, especially Florence. I enjoy working together and promoting their companies. These connections range from designers, travel writers, wellness professionals, and even wine makers!

On the contrary, while I love that you can establish an authentic business relationship with many companies in Italy, at times I am looked at as a young, single, woman and I have to remind the Italian men that I am a CEO just like them!

Luckily, my daily work is great and my main network in Italy is a variety of wonderful businesses run by friends that are both men and women, so naturally it makes planning for guests much easier and fun!

How would you describe the difference between American culture and Italian culture? Do you have a preference between the two?

I love both, that is why I can not choose between which one to live. I love the motivated, creative side of being in America and I love the laid back “enjoy life” mentality of Italian’s.

I think they both have amazing qualities and I appreciate both. I love living between two countries because it reminds me not to take anything for granted, even something as simple as a cappuccino or the New York City Subway. 

What inspires you?

Authentic people, overcoming obstacles, success, manifestation, hope, inspirational video’s (anyone who knows me well right now is laughing because that is my secret weapon) and of course TED talks which was why I was beyond honored to speak at TEDx DBH Mannheim this past November!

But more than anything, I appreciate surrounding myself with other creative, hard working people who are trying to live their dream!

How would you describe a day in the life of?

Oh boy, a day in the life, especially for me can change at any moment. Mostly for me, good coffee, something sweet, a good conversation, an inspiring email from a past client or new contact, and ending the day by doing something enjoyable, whether it be apertivo with friends in Italy or attending a local networking event in NY. I try to work hard, enjoy life, eat good food/wine, and learn every day! 

What do you wish you could tell your 25 year old self?

Stay on track, don’t worry and don’t change anything. When I was 25 I was just meeting my future fiance (whom I later on left) starting a high paying career in wine (which I later was fired), and enjoying life as I was supposed to for that moment.   

If any of that changed I would not be here, right now surrounded by so many amazing things. It is not easy but even if I changed something in the past or gave myself advice, I could of changed my whole path. Call me old school but I believe we can’t change fate!

Advice for those that might want to move to Italy/abroad from the states? I know many of us dream for it to be just like Under the Tuscan Sun, but I imagine there’s a lot more to it. What are some of the important things to know? How much of a plan do you need, how practical is it to just jump on a plane and go with the flow?

I speak about this often with my “ex-pat” friends and we understand, I understand, I get it!

In 2008 my dream was to rent a little apartment in the country of Tuscany, sipping local wine, and learning to cook, just like Diane Lane (I do love that movie still by the way) but I quickly realized, there is no way I could survive in the country with the issues of inconsistent public transportation in Italy, I didn’t really want to learn to cook in the end, and sometimes I just want a pumpkin spiced latte or to walk around Target. 

I was quickly faced with the reality of life abroad. It took me 7 years to get my Italian passport, then forget about the documents and hours of lines you must wait in line for when you arrive in Italy to be considered for a job. For working most of the time you will either be paid less than minimum wage or maybe they will not even pay you at all, this is a common issue, even for some Italians.

Now I am not meaning for this to discourage anyone but rather motivate you to make a real plan. First, think if you still can imagine being without this beautiful country in your life, if you seriously would rather be sitting in a little studio apartment in Florence eating chickpeas rather than in a penthouse in NY then you know it’s the real deal.

I would never tell anyone to give up on their dream because I did not and it worked but I also would not tell them to hop on a plane and think it will all just fall into place (all the time). I know this can happen but even a slight plan is better than nothing in my opinion. 

I would tell you to save up for at least two months of rent money and figure out a job that may work for you.

If you are thinking of teaching English in Italy please know it is not as easy to find jobs, so think of a back up plan and make sure you have all the proper documents to legally work abroad.

If you are thinking of blogging or starting a travel business I recommend to connect with some professionals in the business before diving in, you will be thankful for insider information!

It took me several years to figure out how to incorporate Italy and living abroad into my life but now, my life would not make sense without it.

I am actually writing a book about all these stories of moving abroad, changing my life, and trying to become Italian and my hope is that it inspires others who share similar dreams to keep going, even through the craziness of becoming an expat!

Current mantra?

“I am enough.”

“I am surrounded by the love and knowledge I need today.”

Being around great people and loving what I do is most important to me so this is what inspires my mantras. I do not have to be perfect but rather perfectly happy, in this moment. 


To learn more about Cassandra and Travel Italian Style, visit travelitalianstyle.com or follow her on Instagram.

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