Tuscany Hotels

Establishment neighborhood
Castello di Casole
Località Querceto, Casole d’Elsa
Castello di Casole occupies a 10th century Tuscan castle, set snugly into a landscape of working farmland. Guests might start their day at the break of dawn, wildlife-spotting with a local naturalist. Or ride a horse through a network of country trails. A pack of curly-haired dogs might assist with a truffle hunt. Or none of the above: There’s no sense of urgency here, and visitors who believe in the concept of villeggiatura might spend days on end lounging at the pristine pool and unwinding at the spa, which occupies what used to be the wine cellar. All the hotel suites are well-appointed and comfortable, but the villas, in the former farmhouses that surround the central castle, are standouts.
La Bandita Townhouse
Corso Il Rossellino 111, Pienza
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.
La Bandita Countryhouse
Podere La Bandita, Pienza
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.
Giardino La Foce
Strada della Vittoria 61, Val d'Orcia
This was once the home of Iris Origo, author of War in the Val d’Orcia (required reading if you’re going to spend any real time in the valley). Today, the spectacular palazzos, olive groves, and gardens are run by her two daughters, Donata and Benedetta. If you don’t stay in the bed and breakfast at La Foce or rent one of the villas, make time to tour the gardens. It’s the Versailles of Tuscany. “The regular guided tours give you a chance to peek into this spectacular English garden and hear about its minor but fascinating role in World War II,” says Voigtmann. Images courtesy of Laura Arcelli.
La Bandita Countryhouse (Closed)
Via del Giglio, 12, Pienza
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.
Castello di Vicarello
1 Località Vicarello, Poggi del Sasso
Though it offers incredible views of the Tuscan countryside and an excellent spa, the 12th-century castle-turned-hotel is really about food. The owner, Aurora Baccheschi Berti, is a world-class chef who specializes in Northern Italian cuisine (check out her cookbook here). In addition to whipping up a daily breakfast spread she holds cooking classes (fresh pasta making, for example) using organic ingredients grown right on property. There’s also a working vineyard and an olive grove where you can witness the harvests firsthand.
Rosewood Castiglion del Bosco
Castiglion del Bosco, Montalcino
Situated in the UNESCO World Heritage Site of Val D’Orcia, this centuries-old estate south of Siena is truly incredible: Beyond the fact that you walk amidst remnants of walls from the 1100s, it’s surrounded by Brunello di Montalcino vineyards, there’s a world-class golf course, on-site truffle hunting, and the food is unbelievable. There’s a fancy restaurant, but there’s also a casual pizzeria—and kitchens in the villas where you can feast on bread and incomparably sweet tomatoes. While it's plenty romantic, they have a lot of activities (including cooking classes) for kids.