Italy: The Trip That Started Our Love Affair With Europe

Sometimes the trips that change your life are not the ones you expect. For us, that trip was Italy.

Today, we spend much of our retirement planning European adventures, researching destinations, helping others maximize points and miles, and looking for the next amazing experience. But before 2019, we had never actually taken a vacation to Europe together.

That may seem surprising considering how much travel had already been part of our lives.

Over a career that began in the mid-1980s, I accumulated millions of airline miles and hotel points through business travel. Between American Airlines, United Airlines, and Northwest Airlines, I flew more than 3.5 million miles and spent more than 2,000 nights in hotels. I also earned millions of American Express Membership Rewards points through corporate spending and travel programs.

Travel became second nature. I planned company events, sales meetings, destination trips, family vacations, and personally handled most of my own travel because I found it easier than working through an agency. Along the way, we used miles and points for family trips to Hawaii, Puerto Vallarta, Cabo, Guatemala, Puerto Rico, the Bahamas, Key West, and California.

I booked flights for my parents so they could spend holidays with family. I helped arrange two honeymoon trips to Hawaii for our children, including first-class flights.

But Europe remained unfinished business.

Over the years, we had planned trips to London, Paris, and Amsterdam. Unfortunately, health issues forced us to cancel those plans before we ever boarded a plane. Then came a cancer scare involving my wife. Thankfully, things turned out well, but it served as a reminder that life does not always wait for perfect timing.

By early 2018, after discussing what we really wanted to do with our retirement years, we finally made the decision. It was time to stop saving the miles and start using them.

Italy became our first choice.

We planned the trip for September shoulder season, one of my favorite times to travel. The summer crowds were beginning to fade, temperatures were more comfortable, and prices were generally more reasonable.

Years of travel planning had taught me one important lesson: the best locations and best values usually go to those who book early.

We used United miles to book roundtrip Premium Economy flights from Chicago to Rome. I had enough miles for Business Class, but I wanted to preserve some of my remaining balances for future domestic trips. Besides, my wife has never loved long flights. Living in Chicago gave us another major advantage: nonstop service.

Neither of us wanted to deal with connections, missed flights, or additional travel stress. We wanted to arrive in Europe, start our vacation, and enjoy every minute.

Rome: Our First Taste of Italy

Rome was our first stop and would also become our last. We intentionally split our Rome stay into two separate visits.

For the first portion of the trip, I booked a hotel near the Colosseum where we could easily explore ancient Rome and participate in a guided tour. Rome immediately reminded us why people fall in love with Europe.

The city seemed endless. Every turn revealed another church, another piazza, another monument, another restaurant filled with locals and tourists sharing meals late into the evening.

The city encouraged wandering. And wandering became one of our favorite activities.

Venice and a Special Family Reunion

From Rome, we continued to Venice. We rented an Airbnb with direct canal views, a decision that turned out to be one of the highlights of the entire trip.

There is something magical about waking up in Venice. The sounds are different. The pace is different. The city feels like nowhere else on earth.

An unexpected bonus came during our final evening in Venice: our son was able to join us.

His company maintained offices in Milan, and one of his clients at the time was the Venice Airport Authority. Before our trip, he connected us with members of his Milan team who shared recommendations for restaurants, destinations, wineries, and local experiences throughout Italy.

Those local recommendations proved invaluable. In many ways, that experience shaped how we continue to travel today. Having trusted local insights often leads to some of the most memorable moments of a trip.

Through Tuscany

Together, we boarded a train to Florence. From there, we picked up a rental car and headed into Tuscany.

If Venice felt magical, Tuscany felt timeless.

Rolling vineyards. Hilltop villages. Stone farmhouses. Roads that seemed to wind forever through postcard-perfect landscapes.

One of our first stops was a winery in the Chianti region recommended by my son's colleagues. We enjoyed lunch overlooking the Tuscan countryside while experiencing our first true bistecca.

It was one of those meals where the setting, food, wine, and company all come together perfectly. Those are the meals you remember years later.

Siena and Discovering Tuscany

After dropping our son off in Siena so he could return to work, we checked into La Bagnaia Golf & Spa Resort Siena, a beautiful Curio Collection by Hilton property located on a restored medieval estate.

The property itself was stunning. But the following day became one of the most memorable days of the entire trip.

We kept the rental car and spent the day exploring Tuscany on our own: Montalcino, Montepulciano, and Pienza. Each town had its own personality. Each offered incredible views. Each provided another reason to stop, wander, and stay longer than planned.

In Montalcino, I discovered Brunello wines. In Pienza, I discovered pici pasta. Both remain favorites today.

Sometimes travel changes your perspective. Sometimes it simply introduces you to things you never knew you were missing. This day accomplished both.

Florence and Meeting David

Eventually, our journey brought us to Florence. We returned the rental car and checked into a hotel less than five minutes from the Duomo and a short walk from the Galleria dell'Accademia.

Location has always been one of my highest priorities when selecting accommodations. Being able to walk everywhere transforms a trip.

Florence did not disappoint. The Duomo dominates the city skyline, the streets are filled with history, and of course, there was David.

After having previously spent an afternoon hanging out with Bob Marley in Sorrento, I was excited to meet the second famous person on my Italian journey.

David was considerably quieter. But just as impressive.

Standing before Michelangelo's masterpiece was one of those moments where photographs simply fail to capture the scale and beauty of what you are seeing in person.

The Amalfi Coast, Capri, and Sorrento

One of the most anticipated portions of our trip was the Amalfi Coast. We stayed in an Airbnb in Massa Lubrense, perfectly situated between Sorrento and the famous coastal towns beyond.

The terrace overlooked the Mediterranean. The views stretched toward Capri. Every morning felt like something from a postcard.

One of the biggest advantages of the location was its proximity to the harbor. Within minutes, we could walk to our departure point for a boat excursion that included stops in Amalfi and Positano. Along the way, I even managed a quick snorkeling stop, one of my favorite activities whenever warm water is available.

The Amalfi Coast delivered everything we hoped it would: beautiful scenery, colorful villages, great food, and the relaxed pace that had become one of our favorite parts of Italy.

Pompeii: The Day We Still Talk About

If you ask my wife which day she remembers most from our first Italy trip, she will not say Rome, Venice, Florence, or the Amalfi Coast. She will say Pompeii.

Walking through an ancient city frozen in time nearly 2,000 years ago was unlike anything we had ever experienced. Years later, it is still one of the destinations we talk about most often.

Our visit became one of the defining experiences of our first trip to Italy. Walking through the remarkably preserved ruins brought Roman history to life in a way that books and documentaries never could.

The contrast between the ancient city and contemporary sculptures such as Igor Mitoraj's Centauro created a unique and unforgettable experience that remains one of our family's favorite travel memories.

Back to Rome

We ended our journey where it began: Rome. This time, we stayed closer to Vatican City.

The location made it easy to visit St. Peter's Basilica, the Vatican Museums, and the Sistine Chapel. Standing beneath Michelangelo's ceiling remains one of the defining memories of the trip.

I looked around hoping to thank him personally. Unfortunately, he appeared to be unavailable that day.

What We Actually Remember

When people ask about Italy, they usually expect us to talk about the Colosseum, the Vatican, Venice, Florence, or the Amalfi Coast.

And those places were incredible.

But what we remember most are the moments in between: the quiet walks, the wine shared over long lunches, the views from our terrace, the conversations, the Tuscan countryside, the canal outside our Venice apartment, and the feeling that we had finally stopped rushing and started experiencing a destination rather than simply visiting it.

Italy was the first chapter.

Since then, we have explored London, Bruges, Paris, Switzerland, Amsterdam, Spain, and many other destinations. But every European adventure we have taken since can be traced back to that first trip.

The one where we finally stopped saving our points for someday and decided that someday had arrived.