10 Experiences in Italy I’ve Loved (and a Few Still on My List)

If you’re planning a trip, some of the best experiences in Italy include food tours, gondola rides in Venice, winery visits in Tuscany, and exploring historic cities early in the morning before the crowds arrive.

We’ve enjoyed many of these firsthand, while others, like taking a private boat tour along the Amalfi Coast and staying at an Italian farm, are still on our list. Here are ten experiences worth considering for your own trip.

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 become one of your favorite travel memories.

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.

Our first food tour was in Florence, and even a decade later, we still talk about it. We followed our guide through local markets, small cafés, and places we probably would have walked right past on our own.

Since then, food tours have become something we look for when traveling. In Italy, they’re worth considering in more than one city because the food changes from region to region. What you’ll eat in Rome is different from what you’ll find in Florence, Naples, or Bologna.

I recommend booking a food tour early in your visit. It’s a good way to get familiar with the neighborhoods, learn about local specialties, and find places you might want to return to for another meal.

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 for centuries. 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, well, Venice.

The view from the water gives you a different perspective. You notice the small, crooked bridges, quiet courtyards, and corners you might miss while walking around. Time it around sunset, and the golden light bouncing off the buildings and rippling through the water adds to the experience.

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 becoming rarer these days. Choosing the right one can make the ride that much more memorable.

Learn to Cook As 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.

One of my favorite experiences was taking a cooking class in Florence, up on a terrace with 360-degree views of the city. It was easily a highlight of our trip, and I still think about it when I remember our time there.

Cooking classes often focus on one or two dishes, so start with what you love to eat. Want to make pasta from scratch? Want to learn the secret to a rich ragù? Or maybe master the art of tiramisu? There’s probably a class for it.

Some classes even begin with a market visit to shop for fresh, local ingredients before heading back to the kitchen. Others are set in beautiful places like the Tuscan countryside, a farmhouse in Umbria, or a seaside village on the Amalfi Coast. The setting can be just as memorable 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. Every time you cook that dish again, you’re back in Italy, even if 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.

Visiting a vineyard in Italy is about more than what’s in the glass. You can walk through rows of vines, explore centuries-old cellars, and learn about the winemaking process from the ground up. The soil, grapes, and climate all play a role in how each bottle turns out, and it’s fascinating to see how deeply rooted the tradition is.

Of course, the tasting part doesn’t hurt either. Some vineyards offer small-production wines you won’t easily find outside the region. You don’t have to be a wine expert to appreciate a tasting, and you might even leave with a bottle or two.

Tuscany is one of Italy’s most popular wine regions, and having visited its wine country ourselves, I can understand why. Between the rolling hills, medieval towns, and vineyards stretching across the countryside, there’s plenty to enjoy beyond the wine. You’ll also find Chianti, Brunello di Montalcino, Vino Nobile di Montepulciano, and bold Super Tuscans if you like reds with a bit more edge.

And when you’re sipping a glass of wine on a shaded patio overlooking those hills, it just kind of clicks. This is why people fall in love with Tuscany.

Even if you’re not much of a wine drinker, the vineyard settings, the stories behind the wines, and the chance to explore the countryside make a winery visit worth considering.

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’re setting our sights on something a little more personal: a private boat tour along the Amalfi Coast.

What appeals to me about a private tour is the flexibility. Depending on the itinerary, you might stop for a swim in the Mediterranean, cruise past colorful seaside villages, or spend some time exploring Capri. Some tours also include the Blue Grotto, although entry depends on sea conditions and may cost extra.

Imagine spending a few hours cruising the coast, stopping in a quiet cove, and enjoying the views without a large group tour. Some boats even include refreshments or prosecco onboard. It’s the kind of experience I’d love to plan for our next trip.

You can find private boat tours departing from places like Positano, Amalfi, Sorrento, and Capri. Before booking, compare itineraries, read recent reviews, and check what’s included, such as fuel, refreshments, and any additional entrance fees.

Eating Pizza Where It All Began

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

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

And just because you’re in Italy doesn’t mean you’ll find the same pizza everywhere. Rome, for example, is known for its own style of pizza, with a thinner, crispier crust compared to the soft, chewy Neapolitan version. It’s worth trying both if you’re visiting multiple cities.

There’s no shortage of great pizzerias, but one of the most famous is L’Antica Pizzeria da Michele. It’s been serving pizza in Naples since 1870 and is still known for its traditional pies. Be prepared for a wait, though, because it’s a popular stop.

And don’t skip the street food. On our last food tour in Naples, we tried pizza fritta (fried pizza), a deep-fried, stuffed pizza that can be filled with cheese, tomato, and other ingredients. It’s messy in the best way and well worth trying.

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

hen 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 the history that 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 a Colosseum night tour. Seeing the ancient amphitheater illuminated after dark, with fewer visitors around, sounds like an entirely different experience.

Night tours offer a chance to see parts of the Colosseum that aren’t included with standard admission. Depending on the tour, the experience may include walking onto the arena floor and exploring the underground chambers where gladiators and animals once waited before entering the arena.

Even from the outside, seeing the Colosseum illuminated at night is worth experiencing. But walking through those ancient corridors after dark? That’s something I’d love to do on our next visit.

If a Colosseum night tour is on your Italy wish list, plan ahead. These special tours have limited availability, and tickets can 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 Christmas markets, it looks like a wonderful time to visit. We haven’t made it happen yet because holiday travel gets tricky when you’re juggling things like dog sitting, but it’s one we still talk about planning.

Christmas traditions in Italy vary from region to region. You’ll find festive markets selling handmade gifts and seasonal sweets, nativity scenes displayed in churches and town squares, and holiday celebrations that continue into January.

One experience I’d love to have is attending Christmas Eve Mass at St. Peter’s Basilica in Vatican City. The celebration is traditionally led by the Pope and draws visitors from around the world. Another important event is the Pope’s Christmas Day blessing in St. Peter’s Square.

Of course, visiting Italy over Christmas takes a little extra planning. December 25 and 26 are public holidays, so some attractions, shops, and restaurants may be closed or operate on reduced hours. I’d recommend making dinner reservations ahead of time if you’re staying in a major city.

And don’t forget La Befana, the Italian Christmas tradition celebrated on January 6, when children receive sweets and gifts. It’s another reason to consider extending a holiday visit into the new year.

Visiting Italy during the Christmas season would give us a chance to see a different side of places we’ve already come to love. It’s still very much on our travel wish list.

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 almost 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. Popular attractions are less crowded, the morning light is soft, and you can enjoy the sights without the usual bustle. It’s also a great time to take photos before the streets get busy.

We’ve made a habit of doing this in Florence and Rome, and those early morning walks always stand out. There’s something about seeing these cities before the crowds arrive that makes you appreciate them differently.

If you’re staying in a busy city, set your alarm early at least once during your trip. You won’t regret having a quiet hour or two to wander the streets, grab a cappuccino, and watch the city wake up.

Staying at an Italian Agriturismo Is on Our List

We haven’t done it yet, but staying at an agriturismo, a farm stay in the Italian countryside, is high on our list.

Not everyone realizes this kind of accommodation is an option in Italy. Some agriturismos are simple, family-run properties surrounded by farmland or vineyards. Others offer experiences like cooking classes, wine tastings, farm tours, or meals prepared with ingredients grown right on the property.

You can find agriturismos throughout Italy, but I’d love to explore Tuscany and Umbria this way. Imagine waking up to countryside views, enjoying a homemade breakfast, and spending the day exploring nearby villages.

Each property is different, so it’s worth looking into what’s included. Some offer breakfast or dinner, while others have swimming pools, restaurants, or guest activities. You’ll also want to consider the location, since staying in the countryside may mean renting a car.

When we finally plan an agriturismo stay, I think it’ll be a nice change from staying in the middle of a busy city. It’s another side of Italy we’re looking forward to experiencing.

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