Pienza

This whole area is known for spectacular leather, but so much of it is poor quality and not so nice. This store is what you think of when you think of a chic Italian leather store that no one has discovered yet: wallets, bags, clutches in the softest leather imaginable in brown, black, grey (if you’re feeling safe), and shades like silver, orange, Kelly green (if you’re not). “It also has a limited range of beautiful handmade clothing pieces,” adds Voigtmann.

Tuscany, like any tourist destination in the world, is full of trinket shops and fake authenticity. Aracne is the exception—and one that you’d walk right past if you didn’t know to look for it. “Beautiful blankets and wraps and other textiles handmade on an old loom right in the shop,” explains Voigtmann. It’s the reason you’ll want extra room in your suitcase.

There’s nothing about a 600-year-old Renaissance town that would make you think that the cool kids took over. Then you walk down below the church. “It’s this hipster cocktail bar that was recently opened by a group of young guys from Pienza,” says Voigtmann. “It’s in a historic building overlooking the valley.” This is the perfect place to come after dinner: If it’s warm, sit outside, but the inside is just as lively. Order a Campari spritz, the less-sweet version of an Aperol Spritz, and snack on chips as night falls over the valley. The darker the sky, the louder the music. Fair warning: “It stays open late,” says Voigtmann. “Too late.”

A fantastic restaurant that doesn’t serve pasta is a rarity in Tuscany—in fact, Sette di Vino may be the only one.

“Simply the best gelato” in a town—and a country for that matter—known for its gelato. It’s tiny, there’s always a line, and give up any notion that you could actually get a table. But the gelato flavors change regularly because they’re all based on what’s local and fresh, and BuonGusto has never, not once, served a scoop that’s less than heavenly.

This is Voigtmann’s second property, as lovely and welcoming as his first but located right in the center of Pienza. La Bandita Townhouse used to be the town’s convent—then Voigtmann bought it from the nuns, kept the original centuries-old structure intact, and converted the inside into a place with a state-of-the-art kitchen, high thread counts, and every modern luxury. Whether you stay there or not, make a point to have lunch in the garden. Zucchini carpaccio with parmigiano and taglioni al pesto taste better surrounded by rosemary and lavender bushes.

When Voigtmann and Cohane opened their first hotel almost twelve years ago, they wanted it to feel less like a hotel and more like the house of a great friend with fantastic taste. To say they succeeded would be a gross understatement. La Bandita sits on a hilltop, the entirety of the Val d’Orcia unfurling at its feet—superlatives fail to describe these views. There’s an infinity pool, a bocce court, a poolside bar, an outdoor living room and fire pit: The list of beautiful amenities is too long to list. The chef, Dario Ferrari, is reason enough to come here, as are the beautiful service, the remarkably friendly staff, and the in-room bathtubs. Book the Pig Sty—a freestanding suite that makes it seem like all of Tuscany was just given to you.

“Dopolavoro” literally translates to “after work,” but this café slash wine bar slash trattoria slash restaurant is aces no matter what time you go.

For a dose of the Val d’Orcia’s magic, look no further than La Bandita, a tiny little hotel tucked into a hillside in Tuscany. The bedrooms take into consideration every detail: terra-cotta four-poster beds, crisp Italian linens, and, in some rooms, a lime-green writing desk. It’s at once relaxing and sophisticated, not to mention close to Rome and Florence, which are both a two-hour drive away. The wine-tasting capitals and Old World architecture of Montalcino and Montepulciano are also in close proximity, making the hotel a convenient starting off point for longer trips in the region. Service here—perhaps a result of the property’s owner, John Voigtmann, a former NYC record exec and hotel aficionado—is top-notch, and the staff is incredibly helpful, but quietly so, meaning they’re great at anticipating guests’ every need. The infinity pool is just as special as it looks in the photos, too, thanks to the killer view.