Growing up, vacations meant piling into the car with my family and spending a week tent camping somewhere in California. Yosemite, Santa Cruz, campfires, s’mores—the classics. I was lucky enough to visit some beautiful places, but until I graduated college, I had never taken what I considered a “real” vacation. You know, one with airplanes, hotels, museums, and enough sightseeing to make your feet question every life choice.
Then one day my college roommate casually suggested, “We should go to Italy after graduation.”
Being the person I am, I immediately replied, “Sure!”
I hadn’t spent years dreaming about Europe. I hadn’t researched Italy. I honestly hadn’t thought much about traveling internationally at all. We met with a travel advisor, booked two back-to-back tours, and suddenly flights, hotels, and itineraries were magically taken care of. Easy enough, right? In my mind, I was about to become Audrey Hepburn in Roman Holiday.
Reality had…other plans.
I packed the biggest suitcase I could possibly find because, obviously, I needed options. This was long before smartphones, so I also packed one of those travel phones to stay connected with my family back home.
The tour itself was incredible. We stood inside the Colosseum, wandered through Vatican City, admired Michelangelo’s David, and checked off nearly every iconic Italian sight imaginable. It was an unforgettable whirlwind.
It was also where I learned several very humbling travel lessons.
Florence greeted us with a brutal heatwave. Twenty-two-year-old me didn’t think carrying water all day was necessary, so I spent multiple days dizzy, overheated, and wondering why I felt so awful. (Turns out dehydration isn’t a great souvenir.) The adorable sandals I packed? They looked fantastic…right up until my ankles swelled so much that every evening I had to prop my feet up on hotel pillows.
Then came the biggest surprise.
Somewhere during the tour we learned we’d be traveling between cities by train instead of by coach. Apparently, reading my travel documents would have been helpful. There I was dragging my giant suitcase across cobblestone streets, wrestling it through train stations, and trying—with absolutely no success—to lift it over the gap onto the train. It barely fit anywhere once I got it onboard, and by the end of every transfer I was sweaty, frustrated, and questioning every packing decision I’d ever made. By the time those three weeks were over, I had convinced myself Italy was exhausting and dramatically declared that I would never come back.
Spoiler alert…
I’ve been back multiple times. And each visit has made me love Italy even more. Looking back, I realize Italy wasn’t the problem. My expectations were.
I had unintentionally expected everything to work like it did back home. I hadn’t researched the culture, asked questions, or even thought about how daily life might be different. Instead of embracing those differences, I spent too much time wishing things felt familiar. There were so many little things I wish someone had prepared me for. Dinner doesn’t start when I normally eat. Venice mosquitoes have absolutely no respect for personal boundaries and will eat you alive. Dramamine belongs in your suitcase before taking the ferry to Capri, the sea can be nauseously intense!
None of these things ruined my trip, but knowing them beforehand would have made the experience so much more enjoyable.
Ironically, that first international trip is one of the reasons I became a travel advisor.
When I meet with clients now, I’m not just asking where they want to go. I want to know how they travel. What they’ve loved on past trips. What they’ve hated. Whether they’re excited, nervous, or somewhere in between.
Because planning a trip isn’t just about booking flights and hotels. It’s about preparing people for the experience they’re about to have.
Will every client read every page of their travel documents? Probably not. That’s why I don’t simply send an itinerary and disappear.
Leading up to their trip, I’m checking in, sharing destination tips, answering questions, explaining cultural differences, and helping them know what to expect before they ever board the plane. I can’t promise there won’t be a heatwave, swollen ankles, or a particularly ambitious Venetian mosquito.
But if I can help someone avoid learning travel lessons the hard way and be the support I wish I had, I’d call that a successful trip before it even begins.
-Tashina Hernandez