5 Unforgettable Experiences in Italy You Won’t Want to Miss

Italy has no shortage of iconic sights, but some of the best memories come from experiences that go a little off the postcard path. Here are five favorites from my family’s recent trip to Italy.

A Quiet Sunset Gondola Ride 

After watching the sheer chaos of gondolas jostling for space on Venice’s Grand Canal, I was so relieved to instead glide through the quiet side canals with Christian’s Relaxing Gondola Rides. No traffic jams, no shouting, just a friendly gondolier, the soft slap of water against old stone, and a completely different side of Venice. It was the gondola experience I’d always pictured. Pre-booking is not possible, just show up to the spot on Google Maps and wait your turn.

Private Wine Tasting in a Centuries-Old Castle Cellar

For something truly memorable, a private wine tasting and food pairing in the cellar of a centuries-old castle in Soave is hard to beat. We enjoyed tasting local wines exactly where they’ve been made and stored for generations, surrounded by stone walls with centuries of history. Our tasting guide presented thoughtfully chosen local food paired with each wine in a way that was informative and utterly enjoyable. Pre-booking is required; for more information check out the Cantina del Castello website.

In-Home Cooking Class in Bologna

Bologna is one of Italy’s great food cities, and there’s no better way to understand why than in someone’s actual kitchen. Our in-home cooking class meant rolling out fresh tagliatelle by hand, learning the real story behind a proper ragù, and sitting down to eat everything we’d just made. It was a cooking lesson, cultural exchange, and insanely delicious meal, all rolled into one. Grace hosts up to five travelers in this 3-hour class in her central Bologna home.

Food Tour Through Trastevere

Just across the river from the Centro Storico, Rome’s Trastevere neighborhood was historically a poor area that now is an invitation to wander — cobblestone streets, ivy-covered buildings, and some of the best food in the city. A small-group food tour here was the easiest way to eat our way through the neighborhood without guesswork: think supplì, fresh pasta, local cheeses, and a glass of wine or two along the way, all with a guide who pointed out the history hiding around every corner.

Vespa Tour Along the Amalfi Coast (With a Driver… or not!)

When visiting places with jawdropping scenery, I find that the best way to experience them is on two wheels, with nothing between me and the view. There’s no better way to take in the Amalfi Coast than on the back of a Vespa, winding along cliffside roads with the Tyrrhenian Sea stretching out below me. The catch? Those roads are narrow, twisty, and not for the faint of heart. That’s why I enjoyed our day on Vespas with a driver (which also allows for folks to drive themselves if they prefer and have experience) — I got the thrill and the sweeping views without having to keep my eyes glued to hairpin turns.

* Please note that some of the links above are affiliate links, meaning I may earn a small commission if you book through them — at no extra cost to you. I only recommend experiences I’ve personally loved (or that come highly recommended by trusted clients).

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