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.

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.”

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.”

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.”

It’s not something you would expect to find in Tuscany and you certainly wouldn’t stumble upon it unless you knew it was there, but once you visit Puscina, you’ll start to plot your return. This flower farm was started by two sisters with impeccable taste—and is now one of the best open secrets in the valley. “Take a guided nature walk to a secret pond and learn about wildflower cultivation from these innovative sisters who have transformed their family farm into a sustainable flower-producing business,” suggests Voigtmann.

Short of hauling hay bales out of a field with a tractor, a Vespa is probably the most local way to get around. “This outfitter will hook you up with a guide and bright-red Vespas,” says Voigtmann. “It’s the best way to explore the countryside.”