The Hilltop Tuscan Resort with Something for (Almost) Everyone

Tuscany is the rare place that—somehow, impossibly—lives up to every ounce of its hype. However lush and green you imagine those rolling hills will be, however scenic the narrow roads winding through them, however storybook-charming the historic villages perched atop them: You’re exactly right.

Castelfalfi, an expansive and newly renovated resort built around a historic borgo just an hour’s drive from Florence, is the kind of place that captures all that charm in the most luxurious way.

The village of Castelfalfi has a history that goes back to Etruscan times, but the foundations of the current town (and the origins of its name) date to the 8th century CE, when a Lombard named Faolfo first settled there and fortified the hilltop. Parts of his original castle remain, though the building has been altered and added to many times over the centuries under its various owners. Because this is Tuscany, there is, of course, a Medici connection: Giovanni di Francesco Gaetani, who owned the castle in the 15th century, married Costanza de Medici, and they renovated the castle and built an adjacent hunting lodge.

The town itself is small, and utterly charming. It has cobblestone streets, a tiny Romanesque church, a botanical garden, and ancient stone buildings in which you’ll find a handful of shops, a gelateria, a pizza bar, and one of the resort’s villas, Casa Medici. The old castle anchors one end of the main street and is home to the resort’s newest restaurant, La Rocca (more on that below). Downhill at the other end of the street are the old tobacco warehouse and, just across from it, the hotel’s main building. While the resort occupies much of the town, it feels very integrated—not overbearing.

There are 146 rooms and suites divided between the main hotel building and the tobacco warehouse, along with a handful of villas dotted around the estate. The rooms are large, well-appointed, and luxurious, done in a mostly neutral palette of earth tones with some deep-green accents that echo the landscape just outside. The beds are plush, and the spacious travertine-marble-clad bathrooms are equipped with Dyson dryers and Stefano Ricci toiletries. But creature comforts aside, the standout feature is the view, and the rooms make the most of this with large windows that open wide so you can fully enjoy it.

The estate has six different dining options, each with a distinct personality. Olivina, in the main building, is where breakfast is served. “Extensive” really doesn’t do justice to the scope of the buffet—fruits, juices, granola, yogurt, oats, breads, jams, eggs, cheeses, meats, savory dishes, all kinds of pastries, tea cakes…I could go on (and on). There’s also an à la carte menu, should you prefer that. Olivina serves dinner, too—the menu is Italian, with excellent pastas and beautifully prepared fish and meats. Il Rosmarino, a short walk from the main building, is a trattoria, perfect for a more casual meal of classic Tuscan dishes and wood-fired pizza. The clubhouse down on the golf course and Giglio Blu, the pool bar, are both open for lunch. La Rocca, in the old castle, is the fine-dining option—it has just 24 seats and two ingredient-forward tasting menus (one vegetarian): Think zucchini with cheese sabayon, truffle, and a curry tuile or veal cheek with red prawns, potato mille-feuille, and celeriac cream.

The RAKxa Wellness Spa, also in the main building, has both an indoor and an outdoor pool. The indoor pool has curtained daybeds set around it—a tranquil place to idle away some time before or after your treatment. And it has large windows looking out onto the outdoor pool area and the landscape beyond. There are two saunas, a Turkish bath, hydrotherapy pools, and a full gym with studio space and classes on offer, like Pilates, yoga, and kickboxing. The treatment menu spans both traditional therapies and more technology-forward ones—you can opt for a seven-chakra hot stone massage, say, or a vibrational session with Hypervolt therapy. There are also a couple of outdoor treatment pavilions, set beneath a stand of trees on the edge of the hillside—pretty magical.

Where to begin. You could play 18 holes. A game of tennis. Take a hike on one of the trails winding through the estate. Borrow a bike to explore on wheels. Set up down by the lake for an afternoon of fishing. Try your hand at falconry. Beekeeping. Orienteering. Axe throwing. Wall climbing. You could take a tour of the vineyards and winemaking facility, then follow it with a tasting in the wine shop. Harvest from the olive groves and then sample the different oils the estate produces (you’ll learn, if you don’t already know, that the proper way to taste an olive oil involves swishing it around your mouth and making a loud slurping noise—very satisfying). Take a pizza-making class. If you are traveling with kids, the resort has its own (Montessori-inspired) kids’ club as well as an adventure park with a ropes course, archery, and more.

And if exploring farther afield is what you’re after, San Gimignano is an easy (and scenic) 30-minute drive away, while Volterra is just 35 minutes. Both are quintessential Tuscan towns with lots to see and do.

By far my favorite of everything on offer, though, is the truffle hunting. They do it with dogs (not pigs)—for some reason this was the first question everyone asked me when I said I was going truffle hunting. (The pigs, apparently, are harder to control—more likely to eat the truffles they find than to relinquish them to their humans; they can also cause more damage to the land, and using them to hunt truffles is against the law in Italy.)