16 Via Dogali, 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.
Via Dogali 25, Pienza
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.
La Vineria di Montepulciano
Via di Gracciano Nel Corso 101, Montepulciano
“Montepulciano is beautiful, but STEEP,” says Voigtmann. This “perfect little wine bar” is exactly the place you want to rest your legs. The selection of wine is as impressive as you’d expect from a world-class wine bar in a world-class wine town. The vibe is relaxed, the bar is small and bright, and the salumi e formaggi boards are very generous. Pace yourself—you still have to get back to the car.
Cugisi Cheese Farm
Via della Boccia 8, Montepulciano
Tuscany is as renowned for its wine as it is for its Pecorino, and perhaps no cheese farm does it better than Cugusi. You can tour the dairy, meet the sheep, or cut to the chase and just stock up from the store. Whatever you buy, you’ll wish you bought more. “This famed cheesemaker also offers a picnic-basket service with products from its farm,” says Voigtmann. “It’s the perfect way to enjoy a picnic overlooking Montepulciano.”
Via di Mezzo, Castiglioncello del Trinoro, Sarteano
Monteverdi is a hotel, a bar, a restaurant, a wine bar, a spa, and a handful of private villas, and at the time of this writing, there may very well be plans for an opera house under way. It is mind-blowingly beautiful and luxurious. It’s somehow a tiny village and an outrageously luxurious hotel at the same time. The new cocktail lounge, Enoteca, is “probably the best cocktail with a view in the whole valley,” says Voigtmann. And yes, that’s saying something.
Via Gozzante 67, Pienza
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.”
Sette di Vino
Piazza di Spagna 1, Pienza
A fantastic restaurant that doesn’t serve pasta is a rarity in Tuscany—in fact, Sette di Vino may be the only one.
Via Villa Bianca 15, Montepulciano
This is an “organic, biodynamic Vino Nobile producer just outside Montepulciano,” explains Voigtmann. In a region known for wine tours, theirs stands out. What’s especially remarkable is Salcheto’s “innovative zero-emissions wine making process.”
Buon Gusto Gelateria
Via delle Case Nuove 26, Pienza
“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.
Via Colonica 4, Montepulciano
It’s what you dream of when you dream of Tuscany: Avignonesi is the Platonic ideal of a Tuscan winery, hills rolling in every direction, an estate that could be home to a royal family, and a selection of wines to impress any sommelier. “Avignonesi is the top producer of Vino Nobile,” says Voigtmann. “And its wine-tasting lunch is a great way to let a day completely get away from you.”
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