Romantic vacations are supposed to be perfect, right? Picture this: sipping wine in Tuscany, wandering hand-in-hand through ancient streets, maybe even stealing a kiss under the stars. That was the plan for our trip to Italy. What actually happened? Well, let’s just say it involved a lot more laughing than swooning, and we wouldn’t have it any other way.
It all began the moment we landed in Florence. Greg and I had barely unpacked when we set off for what was supposed to be a peaceful afternoon of sightseeing. I’d dreamed of strolling through the city like the classy tourists we are (or pretend to be). The reality? We got hopelessly lost within the first 30 minutes. Greg had the map upside down, I was convinced I could “sense” where we were, and we ended up wandering straight into what I’m pretty sure was someone’s private courtyard. An old man watering his plants gave us a look that said, “What are you doing here?” We smiled awkwardly, pretending we were meant to be there, and hurried out.
Instead of getting frustrated, we couldn’t stop laughing. I mean, how often do you get to accidentally explore the “secret gardens” of Florence? And honestly, seeing Greg flail around with that map, insisting we were “just around the corner” from the Duomo, was the highlight of my day.
But the fun didn’t stop there. The next day, we thought we’d outsmart our bad sense of direction by booking a guided vineyard tour. What could go wrong with a tour, right? Well, Greg, in his eternal enthusiasm, decided to really impress the guide by asking questions about the wine. Except he got a little too excited, and at one point, when the guide asked him to describe the “earthy tones” of the wine, Greg confidently replied, “It tastes like… dirt.” The guide’s face was priceless. Greg’s face, after realizing he’d basically insulted the wine master’s life’s work, was even better.
I couldn’t breathe from laughing. Greg tried to recover, but every time he opened his mouth, I kept cracking up, which made him more flustered. By the end of the tour, we were basically a comedy duo, but hey, we had the best time. Nothing says romance like laughing so hard you can’t finish your wine.
And then came the infamous train ride. We were supposed to catch a scenic ride from Florence to Venice, a nice leisurely trip where we could relax and soak in the sights. Except… we got on the wrong platform. In typical Greg fashion, he confidently announced, “This is definitely the right one,” and we boarded a train with an air of triumph. Fifteen minutes in, I looked out the window, and instead of seeing rolling hills and scenic towns, we were looking at… the opposite direction. Yep. We were heading south, not north. The wrong train.
I should’ve been annoyed, but I wasn’t. Watching Greg’s face shift from smug confidence to “Oh no, we’ve done it again” was priceless. We spent the rest of the ride giggling like kids, realizing we had no idea where we were going. The conductor wasn’t amused when we finally asked where we were. Apparently, we were halfway to Naples. Oops.
By the time we got off at a random stop and rebooked our tickets, we were starving and ended up at a tiny little trattoria in a town we didn’t even mean to visit. And you know what? That meal was one of the best parts of the trip. We laughed over pasta, toasted to getting lost, and realized that the romance wasn’t in the perfectly planned moments, but in the chaotic, hilarious ones we stumbled into