Entrepreneurship Opens The Door To Heritage and a Dual Life

As Founder and CEO, Cassandra bills herself as a “personal trip planner and expert in slow-travel and authentic experiences throughout Italy. Photo by Maria Riazanova

As Founder and CEO, Cassandra bills herself as a “personal trip planner and expert in slow-travel and authentic experiences throughout Italy. Photo by Maria Riazanova

Is New York the most Italian city in the United States? For over one hundred years her harbors and airports have accepted (though not always welcomed, at first) millions of Italian immigrants who settled in enclaves across Brooklyn, the Bronx, and all of the boroughs, establishing restaurants, bakeries, and grocery stores that successfully recreated some of the best parts of life in the “old country.” So it’s not surprising that New York City is home to the largest population of Italian Americans in the United States (and the third largest in the world.)
Cassandra Santoro olive picking in Tuscany in 2016 photo by Cassie PrenaCassandra Santoro olive picking in Tuscany in 2016 photo by Cassie Prena
Today, the descendants of these Italian immigrants still walk our streets, and some of them own and operate the businesses that kept their parents and grandparents connected to their roots in Italy. Many others have opened scores of new establishments that reflect the essence of contemporary Italian style and the heart of authentic Italian culture. 
 
In recent years, the internet has enabled a new group of Italy-centric businesses, many of them owned by Italian Americans, to flourish. Without the need for a brick and mortar storefront, business owners are free to travel between the U.S. and Italy. Their clients find them online, through social media or content marketing. Moreover, while the prior generation of Italian American businesses were historically owned by men (though women did much of the work) the new wave of online companies are frequently owned by women entrepreneurs. 
 
To learn more about this evolution in Italian American commerce, I spoke with Cassandra Santoro. Petite and vivacious, Santoro telegraphs both charm and authenticity, a natural combination for an entrepreneur. An Italian American who grew up just outside of New York City in Long Island, Santoro currently calls Brooklyn home – the same borough that her grandparents settled in when they arrived from Sicily in the early part of the twentieth century. 
Wine Harvest in Tuscany Cassandra pictured with Wine Maker Daniela Photo by Kelsey Sagen PhotographyWine Harvest in Tuscany Cassandra pictured with Wine Maker Daniela Photo by Kelsey Sagen Photography
Santoro launched Travel Italian Style, a luxury small group tour operator, in January 2015. As Founder and CEO, Cassandra bills herself as a “personal trip planner and expert in slow-travel and authentic experiences throughout Italy.” The company leads between two and four tours each year, with a focus on providing authentic travel experiences, connecting travelers to their Italian heritage, and helping women find themselves through travel.  On recent tours, Santoro has taken travelers to take part in making cashmere at a cashmere farm in Tuscany and to join in grape and olive oil harvests in Chianti.
 
You just landed in New York after spending six months in Italy. What do you most look forward to in your “re-entry”? What part of your Italian life will you miss the most?
I am excited to see my family and friends, especially my Sicilian nonna. I am also looking forward to reconnecting with the networking and travel industry scene in NYC. This time of the year is great, as many travelers pass through Manhattan. 
 
Coming home is bittersweet, though. I know I will miss my many friends abroad. Most of all, I’ll miss the Italian lifestyle. I’ll miss the Italian caffe that had my macchiato ready and waiting when I walked in each morning. I’ll miss the way that Italians prioritize enjoying life over the bottom line.
 
I love the way they do business in Italy. Everybody is so happy. The way they live is so different. You can’t replicate that in the States – as much as you try, you just can’t. Spending part of each year in Italy is a good reminder of why I started this business in the first place – I did it because I enjoy the Italian life and I want to share it with people. 
Travel Italian Style 2015 Women's Tuscany Tour photo By cassie prenaTravel Italian Style 2015 Women's Tuscany Tour photo By cassie prena
How did you end up launching a business in connection with Italy?
My father passed away at just 41 years old. He was born in Brooklyn, to Sicilian immigrants, and he was truly Italian in every way. He would do things that people only do in Italy – the way he had his coffee, the way he ate his fruit. After he passed, I realized I had to see where he came. I first stepped foot on Italian soil in 2006 and immediately realized why my dad was who he was. Though I had never been there before, Italy was comforting, and it felt like home. 
 
I knew that I wanted to motivate Italian Americans to go to Italy and explore their heritage because it really changes how you look at life and your family. Through Travel Italian Style, I get to do that, and I love introducing people to its amazing culture and traditions. 
 
Would you say that your heart is on two continents? How does that impact your life? Do you feel like splitting the year between the US and Italy gives you a unique perspective — if so, what insights can you share?
Living between two places is great but not easy. I seem to be always saying goodbye. I really have not decided where my heart is 100%. But I do believe that living between both countries allows you to appreciate aspects of both that you would otherwise have overlooked. Even a simple phone call in Italy that begins with Ciao, bella! brings a smile to my face. When I’m in NYC I get stressed – it’s a rat race. When I go to Italy, I’m super relaxed. In New York, I appreciate the ability to get what you want; but in Italy I appreciate how simple everything is. I can’t decide which I like more!
 
Where can we find you over the next six months keeping la dolce vita alive in NYC? 
I love Villabata Alba in Brooklyn for a real café macchiato and pastry, Keste on Bleecker street for la vera pizza napoletana and EATALY on Fifth Avenue. 
 
As far as wine bars I love seeing what sommelier Joe Campanale has introduced in his restaurants. I am always discovering a new Italian varietal or producer!
 
Is there anything you know now that you wish you had known when you started out?
I wish I knew then what I know now: that I am fully capable of running this business 100% on my own. It took me a while to trust that I had the ability and the strength to be my own CEO, travel the world and be successful.
 
I think it is extremely important, especially for women, to trust in yourself, believe in your plan, and follow your dreams. I’ll be addressing this topic in an upcoming TEDx Talk in Mannheim, Germany titled “Living through Negative: The Power of the Authentic Self.” Entrepreneurs must keep believing that anything is possible!

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