Today’s Culture with Travel interview is with travel entrepreneur, Cassandra Santoro of Travel Italian Style

What inspired the creation of Travel Italian Style? 

I never actually planned to start a travel agency or be in the travel industry at all! My original goal after college was to work for an event-planning company in New York City. However, after the passing of my Italian-American father, I decided to put these plans on hold and participate in an internship. This time in Italy, the land in which his parents were born.

Upon arrival, I requested a job in public relations and events, but instead was placed in tourism. It seemed close enough to the planning, so I stuck with it. I figured I would stay at this company for three months, and then return to New York and begin working a full-time position in my field of choice.

However, during these three months my entire life changed. Shortly after I returned from Italy, I applied for my dual citizenship, packed my bags again and moved back to Italy – this time for three years. During this time, I took a full-time position for the same tourism company at which I interned.

It’s been over 11 years since that day that I first stepped foot in Italia. I now live half the year in Italy, and half the year in New York City running my company travel company Travel Italian Style (TIS).

With TIS, I create custom vacations to Italy, host one small group tour a year, and even assist others on their Italian ancestral journey!

Where do you typically show people around Italy, and does it vary per trip? 

As a travel planner, I am qualified to plan vacations just about anywhere in Italy.

I plan for solo travelers, families, friends, honeymooners, “babymooners,” and even for conferences and corporate professionals. My clients appreciate mixing up their itineraries with slow travel experiences, and a touch of luxury along the way.

For example, many clients may stay in a beautiful seaside hotel in Positano but enjoy dinner at a local trattoria in the Campania countryside.  Or they may stay in the Florence city center but spend their days exploring small family farms in Tuscany. This is a great way for travelers to enjoy and relax like a typical vacation but also understand the Italian lifestyle in which we call la dolce vita.

For the one group tour I host, I try to choose either a unique location or show the authentic side to a popular destination.  This year we are going to the Naples, Italy. I will bring 6 guests and introduce them this characteristic and animated city during the holidays. I especially love Naples since it has such an interesting reputation for tourists. However, after many years of exploring this location, and spending a month there this summer on my own (living like a local), I am eager to show the true beauty of this untouched city to others!

What are some exciting places (companies, stores, etc) that you work with to feature to customize experiences? (Tell us about your Italian heritage trips, too) 

Italy has so many wonderful possibilities, and I feel confident to say that I have the ability to arrange just about anything! However, some opportunities that clients love are the in-home dining experiences, Vermouth and spirit-making classes, authentic excursions such as visiting a cashmere farm, harvest events with grape stomping, and a family-style lunch with locals, and even private visits to artisan shops in the less known areas of Italia. One place in particular I love is Mariarosaria Ferrara Sandals in Ischia. Mariarosaria is one of the few woman shoemakers in Italy!

Italian Heritage trips are always exciting to plan, as well. This is because we just do not know what and who we will meet along the way.

During one journey, our historian guide Mario was walking on the street with the client during their heritage tour and coincidentally ran into one of the client’s distant family members! That family member brought them to meet another relative and that relative introduced them to another person! By the end of the week, our client enjoyed a family dinner with over 20 of their Italian relatives that they had never met before arriving in Italy.

When it comes to your personal travels, how do you think exploring the local culture of a destination helps you discover its story and layers of history? 

When you take a deeper look inside a country or city your whole perspective changes. The food tastes better, the scenery looks different, and even the sky feels brighter.

The great part is, it doesn’t only help you discover the city’s story, but gives you the time to discover your own. Immersive travel is always the best way for me to look deeper into my goals and myself. It’s the only time I truly let go and let the universe (or in this case my Google Maps) lead the way.  

Share about a particularly memorable trip you’ve been on! Why was it so special?

As a travel planner who has been living back and forth between Italy for 11 years, I can gratefully say I have had my fair share of amazing experiences.

If I had to choose, I would say my most recent memorable experience was being a part of the St.Agata festival in Sicily with the Sicilia Convention Bureau. St. Agata is the Patron Saint of Catania and once a year the town devotes a whole weekend to this beautiful woman. As a Sicilian American this was one of the most incredible Italian religious events I have experienced. I highly recommend it to anyone, especially those of Sicilian heritage.

Overall, I would say most memorable experiences are always from my very first time living and traveling Italy in 2006, when everything was so new. I can remember my first espresso, my first time seeing the Tuscan hills, and even the first time taking the infamous Amalfi Coast drive. Whenever I create an itinerary for a client, especially first-time travelers, I always try to keep this feeling with me in hopes they too have that same sense of awe I felt during my first trip!

What advice would you share with a budding travel entrepreneur?

For someone who is starting out, I would share the same advice I often say during these interviews. Be practical, ethical, hard working, and find your niche. Try to focus beyond the travel aspect of the company but on what makes you different.

For me, I feel a bit unique since I also lead motivational talks, am a storyteller, a writer and happen to live half the year in Italy. All these aspects help create my particular market in the Italian travel sector. It also keeps me learning and growing.

Another example is the story of Kelly Set Go from the Travel Channel. Kelly first learned outdoors land adventure, then to dive, then to fly. After learning all these sports it was only then she felt she had found her niche in the travel world. If she would have stopped in the beginning with basic outdoor land adventures there is a good chance she would not where she is today.

In conclusion, take the time to really understand what value you can provide for the world. Do more of this and I promise you will feel invigorated, passionate, and soar in your career!

Follow Cassandra on her Travel Italian Style website, Instagram, Facebook and Pinterest!