Italy was our first major international trip together, and somehow we've kept finding reasons to go back ever since.
The funny thing is that parts of that first trip feel surprisingly distant to me. At the time, I was deep in building Tatango, and taking a couple of weeks away from work felt like a massive event. Even so, a few memories have stuck with me. Venice was our first stop, and it immediately felt unlike anywhere else we'd ever been. Every winding alley seemed to reveal something new, there were boats instead of cars, and the whole city felt almost too unique to be real.
From Venice we took the train to Florence, explored the city, and spent a day in Tuscany visiting wineries around Montepulciano. We finished in Rome, checking off many of the iconic sights while also eating as much homemade pasta as possible between attractions.
Years later, we returned and saw a completely different side of Italy. We started on the Amalfi Coast, staying in Atrani, which remains one of my favorite travel recommendations. It's only a short walk from Amalfi but feels worlds away from the crowds. We spent our days exploring Ravello, taking a boat to Capri, wandering Positano, eating pizza under lemon trees, and hiking through the hills above the coast.
From there we headed north to Cinque Terre, where we took a sunset boat ride between the villages, learned how to make pesto in a cooking class, and spent our days hiking, eating, and wondering why every meal seemed better than the last. We finished that trip in Lake Como, one of the first places where we seriously found ourselves looking at real estate listings and asking, "Could we actually live here?" We eventually chose Croatia when the time came to buy a summer home, but Como's combination of natural beauty, walkable towns, elegant architecture, and incredible food made a lasting impression.
Since then, we've continued finding excuses to return. We've spent weekends in Rome with Jessica's family, taken more cooking classes than I can count, and even road-tripped through Sicily, which felt completely different from the rest of the country. That's one of the things I appreciate most about Italy: every region has its own personality. Venice feels nothing like the Amalfi Coast. The Amalfi Coast feels nothing like Lake Como. Lake Como feels nothing like Sicily. Yet somehow they all feel unmistakably Italian.
We always joke that once you hit two gelatos a day, you're at peak vacation.
Italy isn't exactly a hidden gem, and there's a reason for that. The food, the scenery, the history, the walkability, the culture—it's one of the few countries we've visited multiple times and still feel like we've barely scratched the surface. If someone asked me to recommend a first international destination, Italy would be near the top of the list.