True luxury in Italy isn’t about velvet ropes or Instagram views, but about the rare kind of access that feels earned, not bought. Stylish travelers today want more than aesthetic, they want experiences rooted in culture, craft, and authenticity. Here are five exceptional ways to travel Italy with sophistication, originality, and substance.
- A Vintage Train Journey Through South Tyrol’s Wine Country
Forget the glass-and-steel speed of modern trains. In South Tyrol, stylish travel means boarding a historic wooden carriage and roll slowly through alpine vineyards that date back to Roman times. As the landscape changes from forests to terraced vines, you’ll stop at family-run estates where Gewürztraminer and Lagrein are still bottled by hand.
Here, it’s a deep dive into a lesser-known region where every vineyard has a story, and every winemaker knows exactly what their soil was doing the year you were born. Add a cheese tasting in a 13th-century mountain hut, and you’ll understand why South Tyrol remains one of Italy’s most refined secrets.
- Hot Air Ballooning Over the Val d’Orcia
It starts just before sunrise. A vintage balloon is inflated in the quiet countryside outside Pienza. As you ascend, the rolling hills of Tuscany stretch into view—striped with vineyards, dotted with cypress trees, silent except for the burner overhead. The experience ends in a remote field where a white tablecloth brunch is waiting: local pecorino, honey still warm from the hive, and fresh pastries served with prosecco.
- Custom Perfume in a Florentine Atelier
Florence is filled with shops, but tucked behind an unmarked courtyard lies a real treasure: a master perfumer’s workshop, where centuries-old methods are still used to compose scents drop by drop. Here, you won’t be picking a bottle off a shelf, but sit with the perfumer to design a signature fragrance based on personal memories, moods, and natural ingredients. The process is intimate, slow, and meticulous. In the end, you leave not with a souvenir, but with something no one else in the world owns.
- Inside the Venice Biennale, Without The Crowds
The Venice Biennale is one of the world’s great contemporary art events, but navigating it solo can feel overwhelming. With the right guide—a curator or art historian—you’ll skip the obvious pavilions and dive straight into off-circuit installations, experimental studios, and private artist salons hidden in crumbling palazzi.
Some of these experiences are invite-only. Others are simply not marked. That’s the point. You’ll come away not only understanding the art, but the context, the politics, and the city itself.
Stay nearby at the Luxury Suites at Ca’ di Dio —a boutique hotel blending heritage architecture with minimalist Venetian design. It’s the kind of place that understands silence as luxury and hosts as curators of your stay.
- Golden Hour in the Ghost Town of Craco
Craco, in Basilicata, is not just a ruin—it’s a place suspended in time. Once abandoned due to landslides, the town’s skeletal buildings and dusty alleyways now serve as an open-air stage for photographers, filmmakers, and travelers who want more than another charming piazza. Book a private photo session with a local photographer. In this cinematic place, it’s about standing somewhere that shouldn’t still exist—and letting it tell a story.
Today’s stylish traveler doesn’t want access for the sake of it—they want meaning. These five experiences don’t just check boxes, but stay with you because they’re rooted in place, time, and people who care about what they do.