When I was younger, my dream was to visit Venice. It seemed to romantic, so otherworldly. As I got older, Tuscany replaced Venice as my top travel destination. I longed to road trip through the rolling hills, eating truffles and roast pork and drinking red wine. But once I really started traveling, Italy kind of fell off my radar. It’s not that I didn’t want to go, per se, but my perception had changed, and I kept opting for other destinations instead.
San Gimignano, Tuscany, Italy
I know more than a few people who felt like Italy let them down. It was too crowded, too touristy, too covered in graffiti—not the fairytale they were hoping for. After hearing their stories, I’d convinced myself that Italy was a place authenticity had abandoned; a once-great travel destination whose soul had been stamped out by overtourism.
Pisa, Italy
When Sean and I were plotting a loose course for this trip, Italy wasn’t on the table. In fact, it became a perverse joke that after traveling for an entire year, we still wouldn’t have visited one of the world’s most sought-after destinations. But then our plans fell apart in October, and Italy wound up being our only real option.
We were hesitant, y’all. Really hesitant. Even after we found out about the flooding in Venice—our first Italian destination—we were both more concerned about drowning in a sea of cheap souvenirs and bad food. But then a funny thing happened: Italy blew us away. We ate our weight in fresh pasta and gelato; marveled at incredible art and architecture; and drank Sangiovese and Chianti at the source. It was the only country we visited that truly felt like an indulgent vacation, and the one place we’re eager to return to sooner rather than later.
Gelato, Ponte Vecchio Bridge, Florence
Sure, we encountered the usual gauntlet of crappy, over-priced restaurants near major sites, but the strategy for dealing with them is universal: Get as far away as you can and eat there instead. We wound through dark alleys in Venice for pillow-soft gnocchi and creamy cacio e pepe. We hoofed 30 minutes across town from the Academia to join Florentines on their lunch break. We ate buttery roast pork, zesty meatballs, and truffle tagliatelle, drank a carafe of Tuscan wine, and we only paid $25 for all of it.
Roasted pork, Florence
We went for beers at a quiet backwater bar on the “wrong side” of the Arno river and ended up doing shots with our bartender. And we took a Roman’s advice and ventured to Trastevere—a world away from the Forum and the famous fountains—for supplì (rice balls) and spritzes.
Piazza Navona, Rome, Italy
There were plenty of pesky souvenir sellers, of course—especially in Rome. And believe it or not, we weren’t in the market for a chintzy piece of jewelry or a “free” rose, grazie. But shooing them away was a small price to pay for seeing the Duomo up close and for marveling at the Fontana dei Quattro Fiumi in Piazza Navona. We got to go into the Colosseum for free, for goodness sake. It felt like we were in a modern sports stadium. I could practically hear the crowd. And I was genuinely impressed by the ancient Romans for the first time in my life. Who cares if two or three guys were waiting outside to ask Sean if he was from Africa?
Duomo, Florence, Italy
But the real secret to our success in Italy had nothing to do with our dining strategies or our ability to steel ourselves against hucksters. I’m absolutely convinced that we loved it because we inadvertently went in the off-season.
We listened to a few self-guided city walks that made frequent references to crowds and heat—but we experienced neither. We booked a popular day-trip through Tuscany just hours before it departed with no issues. We struggled to take a believable picture of Sean at the Colosseum for our silly photobomb series because it just wasn’t crowded enough. (What a problem to have!)
Colosseum, Rome, Italy
With just a few dozen people in the Sistine Chapel when we arrived, we had plenty of room to wander and take in the ceiling from all angles. Our tour of the Vatican Museum and St. Peter’s Basilica took three hours instead of the usual five because we weren’t stuck in a viscous stream of other travelers. (Our guide was flabbergasted and kept commending us for coming at the “best” time of year.)
St. Peter’s Basilica, Vatican City
Yeah, some days were a little chilly. And it rained a few times, so we got a little wet. (Or a lot wet, in Venice’s case.) But otherwise it was a best-case scenario. If Sean and I had been dreaming of a postcard-perfect Italian vacation only to find ourselves elbow-to-elbow with a bunch of sweaty schmoes on the Rialto Bridge, fending off selfie stick salesmen and struggling to get a photo of the Grand Canal without someone else’s camera in it, well, we might’ve been disappointed too.
Rialto Bridge, Venice, Italy
If you’ve heard mixed reviews about a destination you’ve been dreaming of (Paris, perhaps?) my advice to you is this: Heed the warnings and expect some imperfections. Plan your trip for a quieter time of year. Then go and decide for yourself.
Rome, Italy
What’s the first thing you think of when I say Colombia? Cocaine? Pablo Escobar? Narcos? FARC? Terrorism? That’s fair. But what if I told you everything you thought you knew about the country is wrong?