It all started in 2020.
I was packing up my apartment after receiving my tentative job offer for Napoli, Italy. Somewhere in the middle of packing and preparing for this major life transition, I happened to look at the calendar.
For some reason, I wanted to see what day of the week my 50th birthday would fall on, two and a half years later.
And there it was.
My 50th birthday was going to be on a Saturday!
I thought, Oh, this is perfect!
I hadn’t had a birthday party since I turned 30, and I decided right then and there that I was going to celebrate my 50th birthday in Italy.
Mind you, I hadn’t even moved to Italy yet!
But the decision was made. I was going to have a fabulous 50th birthday celebration in the country I had fallen in love with years earlier. I just didn’t know exactly where in Italy that celebration would take place.
Falling in Love with Sicily
My love affair with Italy began in November 2016, during my first visit to the country. But it wasn’t until September 2021 that I experienced Sicily for the first time.
I traveled to Palermo for a weekend with a friend, and from the moment I arrived, something felt different.
I absolutely loved it!
The energy, the architecture, the people, and the food. Oh my goodness, the food!
Some of the best food I had tasted in Italy up to that point.
Palermo reminded me of a smaller Napoli, but there was something about Sicily that made me feel even more at home. I couldn’t quite explain it. I just knew I loved the energy of the place.
I remember thinking, Okay, this is my spot!
And with Palermo being only about a 45-minute flight from Napoli, I knew I would be returning.
Eventually, I visited Catania, where I experienced that same feeling of familiarity and connection.
I loved Sicily so much that I began exploring the possibility of transferring my federal government position to Naval Air Station Sigonella, near Catania.
I tried for several years to make that happen, but it never worked out. That’s another story for another day!
Nevertheless, one thing became very clear to me, Sicily was where I eventually wanted to put down roots.
I didn’t know how or when it would happen, but I knew that Sicily had a special place in my heart.
And so, when it came time to plan my 50th birthday celebration, the location was obvious.
Sicily!
Planning a Birthday Celebration Across the Atlantic
Fast-forward to August 2022.
My 50th birthday was six months away, and it was time to start planning.
I created a private Facebook group to invite my friends and family and share the details of my upcoming celebration. I wanted to give everyone plenty of time to make arrangements, book flights, and prepare for a trip across the Atlantic. After all, I wasn’t asking people to drive across town for dinner, I was inviting them to Sicily!
One of the first people I called was my father.
I said, “Hey, Dad, I’m having my 50th birthday party in Sicily next February. I wanted to let you know, but I know you’re probably not going to be able to come.”
You see, my father had never traveled outside the United States. He didn’t even have a passport.
For more than ten years, I had been encouraging him to get one. “Get your passport, Dad!” But he never did. So naturally, I assumed he wouldn’t be making the trip.
His response surprised me.
“I’m coming.”
I said, “What do you mean you’re coming? You don’t even have a passport!”
He calmly replied, “I’ll get a passport. I’ll be there.”
I couldn’t believe it.
I told him he didn’t have to come, that I understood, and that I knew he loved me.
But he insisted. He wanted to be there. And sure enough, my father got his very first passport and traveled to Italy for my 50th birthday!
A Father’s Love Knows No Distance
My father and I have had a long-distance relationship since 1988, when he moved from Pennsylvania to Indiana when I was 15.
We have always stayed connected through telephone calls, so living far apart wasn’t something new for us.
But something interesting happened when I moved to Italy in February 2021.
When I called him after arriving, he immediately switched our WhatsApp conversation to a video call.
And he has been doing it ever since!
Every time we talk, he wants to see my face. I think it’s so sweet!
I don’t have children myself, but I suppose it doesn’t matter how old your children become. To a parent, they will always be your babies.
A friend later offered an interesting perspective about my father’s decision to travel to Italy.
She said, “He needed to see you. He knows you’re okay, but he needed to see you in person and know that you’re really okay.” That made me think, perhaps seeing me on a screen wasn’t quite enough anymore.
He needed to experience my world for himself.
And when he finally arrived in Sicily, I was amazed. Wow, Dad. You’re actually here!
What made the experience even more special was watching him relax and enjoy himself.
He seemed so comfortable in Sicily. At one point, he said to me, “I see why you love it so much.”
Those words meant a great deal to me.
For years, I had been telling him how much I loved Italy, and now he was finally experiencing a little piece of that love for himself.
I was grateful that my birthday celebration had given him an opportunity to experience another country, another culture, and a different way of life.
It was a beautiful experience for both of us.
Enter Massimo – My Sicilian Brother!
Now, let me introduce you to someone who helped make this entire celebration possible.
Massimo Brullo.
Massimo is a professional travel designer and someone I affectionately call my Sicilian brother.
We originally connected through social media, I believe around 2020, and he later organized my first trip to the Catania area.
That weekend included a tour of Catania, a short hike on Mount Etna, and a wonderful cooking class in a local woman’s home in Avola. It was a fantastic experience!
Massimo was knowledgeable, organized, professional, and genuinely passionate about introducing visitors to Sicily. And he knew everybody! Which, of course, is an excellent quality to have when you’re a travel designer.
When I decided to organize my birthday celebration, I knew exactly who I wanted to handle the arrangements.
I contacted Massimo and asked him to plan the weekend. And let me tell you something, he knocked it out of the park!
Massimo organized the entire birthday weekend flawlessly, coordinating our activities and experiences while ensuring that my guests were well taken care of.
His attention to detail, extensive local knowledge, and genuine hospitality made the entire experience seamless. And I wasn’t the only person impressed. Every single one of my guests loved him!
What I appreciate most about Massimo is that he doesn’t simply organize tours. He creates experiences that allow people to connect with the culture, history, food, and people of the places they visit.
He understands that travel is about more than checking destinations off a list. It’s about creating memories.
I trusted him with one of the most important celebrations of my life, and he exceeded my expectations!
Massimo organizes travel experiences in Europe and the United States, and I wholeheartedly recommend his services to anyone seeking a knowledgeable, reliable, and thoughtful travel professional.
Whether you’re planning a special celebration, a group trip, or a personalized travel experience, Massimo brings professionalism, care, and genuine enthusiasm to his work.
But beyond his professional expertise, Massimo has become family to me. He is my Sicilian brother, and I love him dearly.
Thank you again, Massimo, for helping make my 50th birthday celebration an unforgettable experience!
A Weekend of Sicilian Food, Culture, and Celebration
Approximately 25 friends and family members joined me for the celebration, traveling from the United States and different parts of Italy.
Now, I know my people love me. But let’s be clear. Italy was definitely part of the selling point!
And who could blame them?
For many travelers visiting Italy for the first time, the usual destinations are Rome, Florence, Venice, or Milan.
But I wanted my guests to experience something different. I wanted them to discover Sicily!
Our celebration began on Friday evening with dinner at Carmelo’s Restaurant in Marina di Ragusa. And the food? RIDIC!!!
On Saturday, we visited beautiful Ragusa Ibla for a walking tour through its historic streets, taking in the magnificent architecture and charm of this beautiful Sicilian town.
From there, we traveled to Modica for a chocolate-making experience, where we learned about the traditional process of making chocolate using just two primary ingredients.
And then came the main event!
My fabulous 50th birthday celebration!
Saturday evening, we gathered at the gorgeous Poggio del Sole Hotel near Ragusa for my birthday party.
The resort was beautiful, the service was impeccable, and everything came together wonderfully.
It was an incredible feeling to look around the room and see so many friends and family members who had traveled across the Atlantic and from other parts of Italy to celebrate this milestone with me.
Even the weather cooperated!
It was February, but the temperature was around 70 degrees Fahrenheit. Absolutely perfect.
On Sunday, we continued our Sicilian experience with a visit to an olive oil museum, where we learned about Sicily’s olive oil traditions and enjoyed a tasting. We also had a wonderful wine-tasting experience.
The entire weekend was the perfect combination of food, culture, history, celebration, and the beautiful Sicilian countryside.
And thanks to Massimo’s exceptional planning, I was able to enjoy every moment with the people I love. We couldn’t have asked for a more beautiful weekend.
Celebrating More Than a Birthday
As I reflect on that weekend, I realize that my 50th birthday celebration represented so much more than reaching a milestone age.
It was a celebration of the life I had envisioned for myself years earlier.
When I first fell in love with Italy in 2016, I had no idea exactly how I would make living there a reality.
In 2020, while packing up my apartment in the United States, I made a decision to celebrate my 50th birthday in Italy.
At the time, I hadn’t even begun my new life abroad.
Yet there I was in February 2023, surrounded by people I loved, celebrating my birthday in a place that had captured my heart.
My father had traveled internationally for the first time.
My friends and family had experienced the beauty of Sicily.
And I had the opportunity to share a part of the life I had created for myself in Italy.
It was also the beginning of my next year of living abroad.
Looking around at everyone who had made the journey, I couldn’t help but think about how much my life had changed.
How much I had accomplished.
And how grateful I was for all of it.
Sometimes, when we’re busy living our lives, we don’t stop long enough to recognize just how far we’ve come.
That weekend gave me an opportunity to do exactly that.
I wasn’t simply celebrating turning 50.
I was celebrating the courage to follow my dreams, the freedom to create a life on my own terms, and the joy of sharing that life with the people I love.
What began as a simple decision while looking at a calendar in 2020 had become a beautiful reality three years later.
And Sicily, the place that had felt like home from my very first visit, provided the perfect setting.
I will always be grateful to everyone who made the journey to celebrate with me, especially my father, who proved that it’s never too late to get your first passport and experience something new!
And to my Sicilian brother Massimo, thank you again for making it all possible.
My 50th birthday wasn’t just a milestone.
It was another reminder that when you have a vision for your life, sometimes the most important thing you can do is make the decision to pursue it.
The rest of the journey unfolds one step at a time.
Massimo Brullo – Travel Designer
Next up: Is Living Abroad Really for You? I’ll explore why getting clear about what you truly want is essential before making the life-changing decision to move abroad.