Italy Experiences I’ve Done (and the Few I’m Still Dreaming About)

Why Food Tours Always Make My Italy List

When I’m not in Italy, I’m thinking about the food. The pasta. The gelato. The way a simple meal can feel like a memory in the making.

One of the best ways to tap into that magic? A food tour.

Our first was in Florence—and even now, a decade later, we still bring it up. Not just for the amazing bites, but for how it gave us a feel for the city. We followed our guide through local markets, hidden spots, and tiny cafes we would’ve walked right past.

Since then, food tours have become something we seek out, but in Italy, they’re on another level. And if you’re thinking, I’ll just do one in Rome, don’t stop there. What you eat in Rome will differ from what you’ll find in Florence, Naples, or Bologna. Every region—and honestly, every major city—has its own specialties, flavors, history, and stories to tell through food.

It’s not just about the food—it’s about learning the stories behind it, seeing the neighborhoods, and getting a lay of the land without having to plan it all yourself. It’s fun, filling, and one of the first things I book.

Tour Options:
Experience food tours with local Italian guides: WithLocals
Italy Food Tours with Devour

Seeing Venice by Gondola Is Its Own Kind of Magic

There’s something about seeing Venice from the canals that changes how you experience the city. The soft sway of the gondola, the hush that falls over the quieter waterways, and the centuries-old buildings rising right out of the water—it feels like stepping into another time.

Yes, it’s a classic tourist move, but sometimes iconic things are worth doing. Gondola rides have been part of Venice’s history since the 11th century. And even though they’re no longer a daily mode of transport, the tradition is still alive and feels like a part of what makes Venice… Venice.

The view from the water gives you a different perspective—those small, crooked bridges, the tucked-away courtyards, and the quiet corners most visitors miss. Time it around sunset, and the golden light bouncing off the buildings and rippling through the water just adds to the mood.

Not every gondolier is the same. Some keep it quiet. Others share stories and bits of history that bring the city to life. A few might even sing—but that’s become more rare these days. Choosing the right one can make the ride that much more memorable.

Learn to Cook Like the Italians Do

Some meals are so good, you don’t just want to eat them—you want to learn how to make them. That’s where an Italian cooking class comes in.

Italy is home to some of the world’s most iconic dishes, and taking a cooking class while you’re there turns a good trip into a memorable one. One of my favorites was in Florence, up on a terrace with a 360-degree city view. It was easily a highlight of our time there—something I wrote about when sharing our last trip to Florence.

Cooking classes are often centered around one or two key dishes—so think about what you love to eat and start there. Want to make pasta from scratch? Learn the secret to a rich ragu? Or maybe master the art of tiramisu? There’s probably a class for it.

Some even begin with a market visit to shop for fresh, local ingredients before heading back to the kitchen. Others are set in dreamy spots like the Tuscan countryside, a farmhouse in Umbria, or a seaside village on the Amalfi Coast. The setting can elevate the experience just as much as the food.

It’s also a fun way to spend time with your partner or family or connect with fellow travelers who plan their days around food. And the best part? You get to take the experience home with you. Every time you cook that dish again, you’re back in Italy—just for a moment.

Tour Idea:
Top 10 Cooking Classes in Italy [book here]

Sipping Wine Among the Vines

A trip to Italy doesn’t feel complete without at least one winery tour—and not just for the wine.

Even if you’re not a big wine drinker, visiting a vineyard in Italy is about more than what’s in the glass. You’ll walk through rows of vines, step into centuries-old cellars, and learn about the process from the ground up—literally. The soil, the grapes, the climate—everything plays a role in how each bottle turns out, and it’s fascinating to see how deeply rooted that tradition is.

Of course, the tasting part doesn’t hurt either. Some vineyards offer pours of rare or small-production bottles you won’t find outside the region. You don’t have to be a wine expert to enjoy it—you’ll still learn something new, and probably leave with a bottle or two in hand.

Tuscany is one of the most popular wine regions for a reason. Between the rolling hills, rustic charm, and medieval towns dotting the landscape—it’s easy to see why so many fall for it. The region is even home to eight UNESCO World Heritage Sites, so a simple winery visit can feel like stepping into a postcard layered with history. And, of course, it’s where you’ll find some of the best Chianti—along with Brunello di Montalcino, Vino Nobile di Montepulciano, and even bold Super Tuscans if you’re into reds with a bit more edge.

And when you’re sipping that glass on a shaded patio overlooking the hills, it just kind of clicks—this is why people fall in love with wine country.

Even if you don’t drink, the peaceful vineyard settings, the stories behind the wine, and the slow pace of a tasting tour can still make it one of the more memorable parts of your trip.

Tour Ideas:
Exclusive Private Tuscany Wine Tour & Food Pairing Session [book now]

Dreaming of a Private Boat Tour Along the Amalfi Coast

When we visited Capri, we took a group boat tour around the island—and it was incredible. The views, the sea breeze, the feeling of being out on the water with that scenery all around you… it stuck with us. Next time, we have our sights set on something a little more personal: a private boat tour along the Amalfi Coast.

What’s great about a private tour is how flexible it can be. You set the pace. Stop for a swim in the Mediterranean, cruise past seaside villages, or spend extra time in Capri. Many tours include iconic sights like the Blue Grotto and give you the freedom to decide how much time you want to spend at each stop—or even what you’d like to snack on or sip while on board.

Some boats come stocked with wine or prosecco, and you’ll find yourself anchored in quiet coves that feel a world away from the busier towns. It’s relaxed, intimate, and a beautiful way to see the coast from the water—especially if you’re traveling as a couple or with close friends.

You’ll find private boat tours departing from most of the Amalfi Coast’s port towns—like Positano, Amalfi, Sorrento, or Capri. Take a little time to read reviews, compare what’s included, and book with a company that fits your style.

Eating Pizza Where It All Began

You’ll find good pizza all over Italy, but eating pizza in Naples—the birthplace of it all—is something else entirely. There’s just something about that first bite of a true Neapolitan pie in the city that invented it.

Neapolitan pizza is known for its soft, chewy crust, San Marzano tomatoes, and creamy Mozzarella di Bufala. It’s simple, but the flavor is anything but. Cooked in a wood-fired oven in under a minute, it comes out bubbling and just slightly charred around the edges. The pizzaiolos (pizza makers) in Naples are true artists, and you can taste the pride in every slice.

There’s no shortage of great spots, but one of the most well-known is L’Antica Pizzeria da Michele. It’s one of the oldest in the city and still draws a line before they even open—worth it if you want the classic Naples pizza experience.

And don’t skip the street food. On our recent food tour in Naples, we tried pizza fritta (fried pizza)—basically a deep-fried calzone filled with cheese, sauce, and sometimes meat. It’s messy in the best way and beloved by locals for a reason.

If you’re headed to Naples, make time for the pizza. It’s not just food—it’s part of the city’s story.

The Colosseum at Night? It’s a Whole Different Experience

When we visited Rome, the Colosseum was the one place that left us completely in awe. Standing in front of something nearly 2,000 years old—and that massive—is hard to wrap your head around. It’s not just a landmark; it’s a reminder of how much history still lives in this city.

We toured the Colosseum during the day and loved every minute of it. But next time, we have our eyes on the night tour—an experience that’s said to feel entirely different once the crowds are gone and the structure is lit from within.

These small group tours take you through both the exterior and interior of the amphitheater, including some areas that are usually closed off during regular hours. It’s quieter, more intimate, and gives you time to take in the space without rushing.

Even from the outside, seeing the Colosseum illuminated at night is unforgettable. From the inside, with its arches glowing under the lights? It probably leans more haunting than grand—and we’re here for it.

If this is something you’re interested in, definitely plan ahead. These tours are limited and tend to sell out quickly.

Tour Option:
Colosseum Underground by Night: Semi-Private Tour with Arena Floor
[book here]

Christmas in Italy Is One Worth Planning Around

Visiting Italy during Christmastime has been high on our list for a while. Between the twinkling lights, festive decorations, local traditions, and charming Christmas markets, it looks magical. We haven’t made it happen yet—holiday travel gets tricky when you’re juggling things like dog sitting—but it’s one we still talk about planning.

Italians take the holidays seriously. Many businesses close on Christmas Eve and Christmas Day, so if you’re visiting then, plan to stay somewhere with a kitchen so you’re not caught off guard.

One way to experience the season is by attending Midnight Mass at St. Peter’s Basilica in Vatican City. The service features a full orchestra and choir, and afterward, Pope Francis greets the crowd in St. Peter’s Square. Not in Rome? You can still take part at a local cathedral—every city celebrates a little differently.

Traditions also vary by region. In the south, Christmas Eve dinners are a big deal, while in the north, kids wait for La Befana to arrive on January 6. And no matter where you go, festive markets pop up selling handmade gifts and sweets.

It’s also off-peak season, which means fewer crowds, better hotel availability, and a slower, more relaxed pace. If you’re looking to experience Italy a little differently, this might be the time to go.

Morning Walks in Italy Feel Magical

Early morning walks in Italy are one of our favorite ways to experience a city. Everything feels quieter, slower—and in those first hours of the day, it’s like the city belongs just to you.

You’ll catch locals starting their day, chatting over espresso, opening shop doors, and heading off to work or school. Tourist spots are calm, the light is soft, and you can take in iconic sights without crowds or distractions. It’s also a great time to snap photos you might not get later in the day.

We’ve made a habit of doing this in Florence and Rome, and those early morning walks always stand out. If you’re staying in a busy city, set an alarm at least once during your trip—you won’t regret a quiet hour or two before the city wakes up.

There’s something about that time of day that sticks with you—just you and the city, before everything else begins.

Italian Farm Stays Are a Thing—And We’re Interested

We haven’t done it yet, but staying at an agriturismo—a working farm or vineyard in Italy—is high on our list.

Not everyone realizes this kind of stay is even an option. But it is, and it looks like a pretty amazing way to slow down and experience a different side of the country. Some are simple bed-and-breakfasts set on farmland. Others offer more hands-on experiences like cooking classes, helping with the harvest, or just enjoying farm-to-table meals straight from the property.

It’s also a great way to save money. Many agriturismos include breakfast or dinner, and rates are often lower than hotels in the cities—especially in more rural areas.

Each one is different, so it’s worth doing a little research to find one that matches what you’re looking for—whether that’s something relaxing or more interactive.

When we finally plan one, we expect it to be a much more personal experience than a typical hotel stay—and probably one we’ll talk about long after the trip ends.

BEFORE YOU TRAVEL TO ITALY, CHECK OUT THESE RELATED READS:

• Visiting Italy in October: Why You Should
• Why Traveling to Italy is a Must
• How We Spent 3 Days in Tuscany
• Quotes About Italy You’ll Love