Nothing wrong with any of that, I suppose. But that's not the Italy that's stayed with me for fifty-some years. The Italy that changed me wasn't the one I planned. It was the one I stumbled into when I got lost, when I let go, when I trusted a stranger's gesture instead of a guidebook.
Italy reveals itself differently. Not when you grasp at it, but when you open your hands.
Are you ready for Italy? Or are you only ready for the Italy you've already decided on?
So here are five experiences for your surrender list. Understand this: these aren't things to collect. They're ways to fail by tourist standards—and succeed by Italy's.
1. WANDERING: Surrender Your Need for Destination
Get deliberately lost in a southern hill town. Inland Calabria. Inner Sicily. The hinterlands of Basilicata. Places where tourists don't go because there's "nothing to see."
Turn off your GPS. Don't make a restaurant reservation. Walk.
Follow the smell of wild herbs floating down from the hills. Trust a sound, a stranger's direction, the way light falls on a particular alley. The confusion is the experience, the lostness is the point.
You won't find this at the Spanish Steps. You have to go where the road ends and trust that something will lead you somewhere worth being.
2. DISCOVERING: Surrender Your Fear of Missing Out
Find your morning coffee bar in Venice or Rome. Not the best one. Not the one with reviews. YOUR bar. Go back every morning until the barista knows your order.
Step 100 meters away from San Marco and you'll find the quiet, almost deserted village that makes Venice bearable. The locals tolerate tourists in their typical Venetian manner—which is to say, they live here, we don't. We will leave, they will stay. It will always be their Venice, not ours. As it should be.
I learned this returning to Italy in 2023 after a four-year absence. I found a quirky little wine bar near my hotel, Ozio, specializing in natural wine. I sipped a Sicilian white—Catarratto-Zibibbo, a skin-contact orange—instead of the ubiquitous Spritz. Simple, dry, legitimate—everything the Spritz isn't.
Walk down the road, take a right, then a left. Find something no one knows about except the locals. You won't starve. And you might run into something better than all those pages of recommendations. Use your gut, listen to your heart.
The real Italy exists behind the heavily touristed façade. But you have to be willing to miss the "must-see" to find it.
3. PILGRIMAGING: Surrender Your Hunger for Spectacle
Choose Ercolano over Pompeii. An Umbrian hermitage over Assisi's basilica. A Renaissance-era olive orchard on a Calabrian escarpment where a Scandinavian importer once asked to be left alone for hours, just to sit among trees that have never seen Florence or Venice or the Vatican.
I lived in a trailer outside Assisi in 1977 for three weeks, five dollars a day. A short walk led to what was once a stall where they cooked food—local, healthy, humble. No crowds, no queues, just the simple Italian table. Until the New York Times "discovered" it decades later.
Sacred geography reveals itself in solitude, not in lines. You won't get the photo (or the "selfie") everyone else has. You might not even understand what you experienced until years later. But that's pilgrimage—walking toward something you can't quite name, letting it change you without fanfare.
St. Peter's used to be a place where you could park your car, have a picnic lunch on the steps, take your time. Now it's all restricting and queuing up. "Move on, hurry up, no pictures, people are waiting."
Go where the waiting isn't necessary. Go where silence still exists. Walk up the hill to Parioli and find a Rome for Romans and other wanderers.
4. WORKING: Surrender Your Role as Consumer
Get your hands dirty. Harvest olives. Pick grapes. Help prep a village sagra. Work a fishing boat for a morning.
I arrived in a hilltop town called Bucita in Calabria in 1977, following the smell of wild herbs and figs baked in their leaves floating down from the hills. A storm threatened. The family needed hands in the fields for harvest. Like goats we swarmed the vineyards, competing with the bees for the nectar. The elements dominated everything—sun, rain, lightning, thunder—earth, alive and moving.
Years later, I spent days picking olives in Tuscany—900 pounds over several days, thinking about Italian work songs, dodging wasps. Tedious, physical, real.
Or maybe you end up sitting in someone's home at night, drinking their wine. Below you in the basement, thousands of crushed grapes fermenting. Above, a bare bulb lighting the room. The elders talking into the early hours of the morning. That's where I learned wine—not in books or at fancy tastings, but in rooms like that, with people who made it.
You understand terroir through your body, not your palate. You earn your place at the table differently when you've worked for it. Your muscles ache. Your hands smell like earth or oil or fish. And the meal that follows tastes like nothing you've ever paid for.
5. FOOD AND WINE: Surrender Your Expectations
Find a no-menu trattoria. Or better yet, end up at someone's table where you eat what you're given.
I had one of these experiences in the hilltop town of Cirò in Calabria. L'Aquila d'oro—four tables for maybe eighteen people, a "truck stop" most would drive right by. The wife cooks. The husband and son serve. What followed was three hours, eighteen courses of throw-away food becoming revelation.
Baby goat intestines on oregano branches. Fava bean skins—tough, stringy things normally discarded for the prize inside. Ricotta that was milk in the creature yesterday morning. Not Saveur-magazine perfect. Not pretty. But memorable in ways no Michelin meal has ever been.
"This is the poorest of cuisines," my friend Paolo reminded me. "Made from things nobody in the city hungers for. Wild onions, herbs, parts of animals that get discarded, skins of plants no one would think were edible."
Throw away food. Or throw it down food, which is what we did.
If I served this meal to some friends back home, they might ask, "When are we going to start getting the Italian food?" But others would get it. They would understand they were in the kitchen of a woman from Calabria, tasting something out of this world that comforts and nourishes and is so delicious.
The same goes for wine. Skip the trophy bottles. Order the vino della casa. That house wine in many Italian trattorie is better than most wines you can buy in American supermarkets. Simple, fresh, for the moment. Go straight for it. You'll seldom be disappointed.
Before You Go
These experiences share one requirement: you have to be ready to fail by bucket-list standards.
You might not get the photo. The directions you followed might lead nowhere.The winemaker might be out in the fields. You might sit on that bench for an hour and feel like you wasted time.
But if you're ready for Italy—truly ready—that won't matter.
Italy isn't a checklist. It's not a conquest. It's a country made up of people with feelings and emotions, with a culture that doesn't perform for tourists. Step off the trail everyone else is on.
Get lost. Sit still. Work. Eat what appears. Trust the locals over the algorithm.
Let Italy be Italy. And let it change you in ways you didn't plan.
Going to Italy—that's a good fortune most people never have. Don't waste it on checklists. This is one of the most intimate, beautiful places humans have created. Slow down enough, and it will let you in. That gift is worth more than any bucket list could promise.
Other reading: Italy is ready for you - Are you ready for Italy?