I never felt I would just be someone who sells travel. I knew I wanted to organize travel but not in any typical way. Of course I wanted to share the wonderful local life of Italy and the beautiful sites of Bella Italia. However, I decided I wanted to focus on the journey of the traveler and what the beautiful country of Italy can bring to them.

We all experience life in our own way. So why would it be any different for travel. This is what Custom Travel is all about. And this is how and why Travel Italian Style was born.

Experiencing Life on the Amalfi Coast in 2018

My personal Italian journey began in 2006. Italy spread through my soul and the connection to my motherland was immediate. For those who do not know my story of Italy, it began after the untimely loss of my Sicilian dad to cancer in 2002.

I was able to launch my company in 2014 after many years of living, working, traveling Italy, long conversations with my Sicilian nonna, obtaining my dual citizen and preparing myself spiritually and physically as a business owner. I worked hard towards this goal until I made my dream of living 6 months traveling Italy and 6 months in New York City come true.

In recent years, I spend 6 months traveling Italy before returning to NY before the New Year and my birthday. I do this mostly for work. The idea to is to meet and greet our partners on the ground each year and to find new experiences. However, it is an important part of my personal journey as well. When I return, this is the perfect time for me to reflect on my accomplishments, future goals, and what I have learned. Reflection is such an important part of the entrepreneurial lifestyle.

This year I thought it would be insightful to share with you what I learned. In this article you will find travel tips (about the places I visited in Italy), situations that made me grow as a CEO and business owner , and even some life lessons. I hope it brings you some light today on this 28 Day of December and for the New Year.

Since it’s my 35th birthday here are 35 things I wanted to share. Andiamo…

My 20th Region of Italy - South Tyrol 2018

The region of Campania beyond Amalfi Coast is amazing too!
(Travel Tip)

I have spent years traveling and working in the Campania region of Italy. From Naples to the Ravello, I have immersed myself quite a bit, especially in recent years. I have already experienced life on the Sorrento Coast and Naples but this season I extended my knowledge a bit further. I chose to spend two months in an apartment right on the coast.

Besides experiencing local town life, I had more time to exploring less visited area. For one, the wine country around Avellino and the coast leading up to the countryside is quite and amazing and an underestimated place.

I was also happy to explore Cilento this year! The sea, the towns, the views, it all was memorable. As this is the area where the Mediterranean diet started, you can imagine the food. It’s a travel planner and travelers dream!

2. Sometimes you have to let go (Life Tip)

I am learning through this journey that most things are out of our control. No matter how much I try to cling on. You can’t change the world to accommodate us. So it’s better just to leave it at that. Dwelling on anything doesn’t get us that far. Plus letting go usually leads to more inner peace for ourselves and for those around us.

3. You can’t know every single thing about ever-single thing (Travel + Life Tip)

On a 4 X 4 Exploring on Mt. Etna with International Photographers and Instagram Professionals - 2018

I put so much damn pressure on myself to learn every single thing about all 20 regions in Italy that I have visited. Then one day I realized it’s impossible. I also remembered that is why I chose to be a CEO and Travel Planner not a tour guide. I can hire one of thousands of licensed tour professionals throughout the country to guide our clients. Art historians, archeologists, drivers, and guides spend their life learning about their region. I am leaving that to them and doing what I do best. My skill is traveling and learning about my second home country. Then I assist others with planning their experience. I think that is pretty awesome and important too.

I decided that in 2019 when people make a snarky comment about not knowing things such as artist from Naples or that restaurant in Sardinia, I will respond with “Wow, you are probably right” then I will move on. I am 100 percent confident in the knowledge I obtained from traveling over 13 years in Italy and my life as a dual citizen of both the USA and Italy (among many other things). Plus, thanks to my lifestyle I bet there are a ton of things that these people do not know (that I know) about Italy, life, and beyond!

4. People will disappoint you But It Doesn’t Kill You (Life Tip)

In 2017 both a former client and intern took advantage of me and my services in order to start their own travel business. It’s not the start of their businesses that effected me. It was their unethical approach that was hurtful, and invasive.

Then in 2018 a vendors did some shady stuff with money. Sometimes I get scared to think what 2019 might bring but mostly I can not longer waste so much time stressing about this anymore. There comes a time to realize what others do is out of your control. The only control you have is how you handle situation. This is what makes you a true contender at life. So from this point forward, gone are the days I waste worrying about these types of people. I will no longer let people who take advantage of me, my time, and my business take over my life. And if this situation does come up again, I am moving on quickly (no need to let their insecurities attach to me).

Sunrise on a December Morning - Rome Italy 2018

5. Rome is not as touristy as you think (Travel Tip)

For years I bought into the whole “Rome is too touristy” thing. I avoided this city and stuck to selling the basic tours as most travel agents do.

However, at the end of 2018 I decided to give it the chance it deserved. And I am so glad I did! I spent significant time here. Luckily I made some wonderful Roman friends who brought around the city and surrounding regions.

I realized that there was much more to share than you can even believe. I can’t wait to offer these unique experiences to travelers in 2019 (and most are right in the center)!

6. Italy has amazing Health Care (Life + Travel Tip)

Post Surgery with my doctors in Milan - 2018

Back in March my doctor found a lesion in my body. Which was pretty damn scary. Luckily we could control the situation if taken care of quickly. Although, it was scary to go outside my home country, I decided to go forward with the surgery in Milan. This was the best decision I ever made. The doctors were thorough, kind, caring, and a fraction of the cost of USA healthcare. I love America but Italy may have the upper hand on this one.

7. I need to learn how to “Yacht Watch” on he Amalfi Coast (Interesting fact)

Did you know this is a thing? People know the names of the yachts and watch from their homes! They usually know the name of the yacht and which celebrity is currently traveling with it. The summer is my busiest time of the year as a travel planner but I will make time for this in 2019 during my stay on the Amalfi Coast. ;)

8. NYC has energy I need a few months out of the year (Fact about me)

I love both the USA and Italy. When you step foot in both of these locations you can feel the immediate difference. Who agrees? I love them both and grateful to live between them but I am not sure if I could live without being in NYC for at least a bit.

9. Visiting Every Single Region of Italy was worth it (Travel Tip)

South Tyrol Italy during my research visit - Region #20

This year I completed my visit to all 20 regions of Italy. What starts as a personal goal proved to be an important part of being a travel planner. It’s a great way to fully understand this amazing country and what it has to offer! The best part is I never really planned to make this happen, the universe simply opened the doors to this all for me.

10. Stop trying to keep people in Your life that do not want to stay (Life Tip)

I found I spend too many hours a week trying to please other people. I am mostly sacrificing my own health and dignity to keep people around. Many times it caused me to change for the worse just to get their approval. If you find yourself trying to please someone or keep them happy (more then enjoying their company) then move on. Stay near people that inspire and motivate you. Or as motivational speaker Eric Thomas says “Don’t go fishing with people who can’t help you catch anything.”

11. I like my hair shorter better (FAct About me)

I have had my hair pretty long for most of my life. This December I cut it short in Florence thanks to Wave Florence. I feel like I might keep it short forever now!

12. Friuli needs another visit (Travel Tip)

This region literally left me in awe. I couldn’t believe the beauty of Trieste and it’s surroundings. I am going back in 2019 and you should consider visiting!

13. Religious festivals are a special experience in Italy (Travel Tip)

This year I had the honor of attending the World’s 3rd largest Religious Festivals and one of Italy’s most well known, St. Agata in Catania. This inspired me to travel with a local friend on the Amalfi Coast to several local saint festivals throughout the summer. I love the energy during this time. Even if you are not religious it’s still such an intense and beautiful experience. Plus the food is usually A+. ;)

Celebrating one of the many Saints on the Amalfi Coast - 2018

14. You do not need to go into deserted towns or find an old nonna for authentic Italy (Travel Tip)

These days people get really hyped up with this whole “authentic” and “off the beaten path” travel. I get the ideas as I used to push it too. This is before I actually spent most of my time in Italy.

As a sort of local, I believe you can find authenticity anywhere. For example, a family home of a dear friend in Rome overlooks the Colosseum. I also had a beautiful encounter right in the city center of Florence. A local guide brought me to meet a special artisan. He shared a touching story about how he left working with an internationally acclaimed company to start his own project in his home region of Tuscany. He cut his pay in more than half and started his business. I had the pleasure to meet him, see his shop and hear his inspiring story. This all happened 10 minutes from Piazza Duomo (the city center).

If you have time to travel to new and less visited cities, that is great. However, if your time is limited and your goal is to know the local life then consider this. Do not get so stressed about going so far out of the city center. You can do this anywhere if you have the right contacts!

Finding local friends and experiences is closer than you think - Wedding Fun with Italian friends in Arezzo Italy - 2018

15. Soave (white wine) from Veneto is a damn good white wines (travel TiP)

Thanks to my friend Donna from Slow me Down Escapes I now have a better understanding of this wine and the wine country around Veneto. I can’t wait to go back in 2019!

16. The real Home from Under the Tuscan Sun Does Look As it Does in the Movie (Movie/book Tip)

This past Fall I had the wonderful opportunity to be part of the Dream of Italy special in the real life house of Author Frances Mayes from Under the Tuscan Sun. It’s amazing that Frances Mayes words in the book and the movie perfectly recreated this home. Walking through the grounds of Bramasole give you the feeling of being a part of the book, movie, and the inspiring life of Frances.

During the Filming of PBS’ Dream of Italy - Under the Tuscan Sun - 2018

It was so warm, welcoming, and Frances and Ed Mayes were so kind and generous! Stay tuned to see the house, my cameo (ha) and Host Kathy McCabe in her upcoming Under the Tuscan Sun special here.

17. Listen more than you speak + don’t give to get (Life Tip)

I don’t think I need to elaborate more on this. It’s a common trait as a human being. We need to do this more. If you listen you will understand and see life more clearly than ever. Also, if you want to share or gift someone, just do it. Don’t ever expect something in return. Because then this is not in fact a gift it’s an obligation.

18. You have to work hard but you also have to prioritize your time (Life Tip)

I was always told, “work 18 hours a day” or get up at 3am. These things may be true but really I still believe that you can get work done in half the time. It’s important to prioritize your time and work the right way before driving yourself into the ground.

Atrani Italy - one of my many “home towns” in Italy - 2018

19. Italy is a must see during the holidays (Travel Tip)

This year I made a point to stay and experience Italy during the holidays. I haven’t done this since 2008. Wow, what a beauty. It’s a completely different experience but well worth it. It will be a suggestion from TIS for our clients in 2019 and beyond!

21. Your biggest support group can be those people you never met (life tip)

I have spent the last year interacting with a supportive and motivating group of amazing entrepreneurs. These business owners are not in travel and we have never actually met! But when I need them they are there and they listen. They get it. The community is brought together by a coach and fellow business owner who does this at no cost. He gives everything but expects nothing but for us to show up to our online weekly tasks and to keep pushing on this journey. My point (besides Matt being a good, honest person trying to do good in the world) is that we need to think outside the box in order to grow in life. There are ways if you keep your ears, hearts, and eyes open!

22. Keep going even if you think no one is watching (Life tip)

I know this sounds like some cliché quote but I actually believe it. There are many cases where we are looking for validation in order to keep going. Instagram causes this stress and can be quite frustrating at times. Some days you get 900 likes and others 100. But it shouldn’t be an excuse to stop. You must keep going, even if it’s just for yourself. You never know who, what, and when will bring you to the next level.

23. You Do not need to have 100K followers to be a top player in your field (Life Tip)

On that note please remember your Instagram or social media following is not what defines you. I get it and often find myself caught up in this too. But my new goal for 2019 is to attract people who recognize me for my talent and my authenticity. I will not be judged by the number of social media followers I have total.

24. Helping others does not mean scarifying your own self (Life Tip)

You can be a giver but don’t give all your energy and strength, which scarifies you and your well-being. Give what you can but walk away when it comes too much.

25. dont believe the rumor “Northern Italians are cold” (travel tip)

I have heard this for quite a while. Yes, there is a difference in personalities. However, I happen to like the traits of both. HA! I have only met and work with professional, hard working, kind, fun, Northern Italians. I officially love people from all of Italia!

Exploring Northern Italy - 2018

26. People who take short cuts do get ahead (Life Tip)

I know that stinks right? But it’s true and surprising how many people take this route. But I still do not want to be the them.

27. Working with another culture is not easy (life Tip)

Every year I understand more about this country. And every year I realize how different work in Italy is vs. America. I will be forever learning but also forever grateful to have this opportunity.

29. My Italian needs major work (Fact)

Am I fluent in Italian? Well, I can live and run a business focused on country. However, can I speak grammatically. Not as well as I should. I can use some major grammar help. I was recently interviewed (in Italian). It challenged me to step out of my comfort zone and inspired me to go forward with learning even more in 2019.

30. You should dress up as much as possible (Italy Tip)

Italians say that La Bella Figura is the way to live and I finally believe it. America often left me in yoga pants and work out gear for half the morning. Italy inspires me to work out before 8am, get on my shoes and put on my lipstick even for just a coffee. Do I do it everyday? No but I feel damn good when I do it. I get it now. I am going to embrace this even more in the future. More lipstick and heels for me. ;)

Practicing my best La Bella Figura on the Amalfi Coast 2018

30. Pizza is still my favorite food (travel tip)

I thought my palate would have evolved a bit more (living and working in Italy and the wine industry). However, I have to say Pizza is still my go to. I especially love visiting the Naples area. Whether it’s 3 euro take out pizza or a sit experience at the famous Sorbillo, the pizza is better than anywhere else in the world (for me at least). It is worth eating several times during your visit to Campania.

31. Umbria and Le Marche are the new Tuscany

Ok, so these regions have heard this claim for many years but I am ready to embrace it. There i so much to offer and I am excited to focus on experiences and organize travel for clients in the coming year.

32. I need to learn to drive in Italy (travel tip/fact)

Preferably a Vespa. No more excuses.

33. I will spend more time in the regions I Do not love

Sardinia is my least favorite region in Italy and probably one of the most beautiful. I will give it another chance. I learned that traveling is more about understanding the culture and the people. Not necessarily the landscapes. Sardinia was a great reminder of that.

34. I will become a Fortune Top 40 under 40 sometime in the next 5 years (Life tip)

You think I am crazy? Is it possible for me to be one of the most successful people in the world? Yea, sure I believe so. What we believe is what we become. Set your expectations high. #liveyourdream

35. I will believe in myself and the work I do (life reminder)

Each year after my travels, I reflect on the work I have accomplished, I congratulate myself then set new goals. We should all do this and say this mantra to ourselves everyday (no matter where we are in life). There is never a peak to your journey, especially being a business owner. Just look at Amazon, Starbucks, Facebook, etc. They are never content and they are always raising the bar.

I recently saw a friend share this great quote from Michelle Obama which says it best, “For me, becoming isn’t about arriving somewhere or achieving a certain aim. I see it instead as forward motion, a means of evolving, a way to reach continuously toward a better self. The journey doesn’t end.”

I am excited for this never ending - evolving journey of Italy, travel, life, and lessons. Buon 2019 Everyone!

*And Please feel free to share what you would add to this list or an important lesson you learned this past year.

I hope you consider traveling with our Custom Travel Planning Service in 2019. You can find more information at this link.

Also, be sure to join our newsletter. Starting January we will be sharing bi-monthly tips for traveling Italy. Join us here.

Meet the Author

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 in hopes to inspire others on their journey. Cassandra's highlight appearance was being a speaker in Germany for TEDx DHBW Mannheim.

Cassandra currently lives between Brooklyn, NY & Italy. Follow her adventures of life between two countries on Instagram.

The region of Campania beyond Amalfi Coast is amazing too! (Travel Tip)