You Can Go Truffle Hunting by Bike on This Dreamy Tuscan Day Trip

Visit one of Tuscany's best truffle farms by bike and hunt for truffles alongside adorable dogs.

Truffle hunting
Photo: Courtesy of Rosewood Castiglion del Bosco

The wheat fields are fallow in the Montalcino region of Tuscany, and the wine harvest has just concluded, the hillside vines stripped of their Sangiovese Grosso grapes.

Under the ground, however, in the clay soil called Crete Senesi that marks Montalcino's distinctive terroir, another crop — the truffle — is about to come into bloom. At the Azienda Loghi, one of the area's most prominent truffle farms, located on a high rolling hill with panoramic views, Valentino Berni, wielding a long-hooked staff, is leading me down a muddy slope into a cool, shaded forest. Signs to either side announce: Raccolta di Tartufi Riservata ("reserved for the collection of truffles").

Suddenly, Berni's dog, an eleven-year-old Italian pointer mix named Sally, bounds ahead, and furiously roots in a patch of muddy ground. Success!

This delightful forest excursion is one of the many customizable experiences now offered by Rosewood Castiglion del Bosco, part of a 5000-acre, 800-year-old wine estate nestled in the heart of the UNESCO World Heritage Site of Val d'Orcia. Its Tuscan fantasia of a hotel, replete with 12th century castle ruins, was founded in 2003 by Massimo and Chiara Ferragamo, of the eponymous fashion company.

Truffle hunting
Courtesy of Rosewood Castiglion del Bosco

The region's fabled Strade Bianchi, the undulating gravel "white roads," have become a favorite of bicycle tourists. Both Loghi and the Castiglion are on the route of L'Eroica, the region's famed annual one-day cycling event; the hotel can arrange for cycling enthusiasts to take vintage race bikes to explore the legendary L'Eroica bike track in Chianti.

I'm a more moderate cyclist. The hotel is around 12 miles away from Azienda Longhi, and its hills can easily be tackled with one of the property's e-bikes. (And, of course, there's no shame in four-wheeled transport, which can also be arranged).

Sally is one of the farm's 14 truffle-hunting dogs, all of which are female. "Female dogs are calmer," Berni explains. Like all of the farm's dogs, Sally was trained at an early age, a process that begins by adding truffles to the dogs' food. "If they don't eat it, they have no love for the truffle," says Berni, "and it's very difficult to teach."

Truffle hunting
Tom Vanderbilt

As Sally finds her target, Berni shouts a series of short, sharp commands, and sets off at a full sprint before the dog can dig up — and damage — the object of the hunt. As I arrive, Berni has already extracted a large black winter truffle from the ground. If the vaunted white truffle is, as Berni explains, the "Ferrari," the black winter variety, while still commanding prices this time of year around 800 euros per kilo, is more like a sturdy Fiat.

He shows me a specimen, which might be mistaken for a lump of Tuscan clay. The smell, fulsome and mysterious and vaguely intoxicating, permeates through the top note of wet soil.

The potency of truffles begins to decline the moment they're harvested, which is why they'll be shipped next-day air to restaurants in New York and London, and shaved onto a plate some 24 hours after they were first scented by one of Berni's dogs.

Truffle hunting
Courtesy of Rosewood Castiglion del Bosco

Or sometimes, they'll be sent a short drive away, to a place like Rosewood Castiglion del Bosco, where I gleefully leveled a memorable dish of tagliolini con tartufi after a "divine wine" massage in the hotel's spa using oil infused with pomace, the crushed residue from the vineyard's grapes. (Why can't every massage end with a glass of Brunello di Montalcino wine and a generous plate of cheese, as this one does?)

But back to the foraging expedition. After we collect a good-sized bag of truffles, we head to the farmhouse for a lunch overseen by Massimiliano Giovannoni, who has returned to Tuscany after a global tour that included a stint as sommelier at New York City's Del Posto.

Truffle hunting
Courtesy of Rosewood Castiglion del Bosco

The lunch includes pasta with truffles, locally sourced turkey with pureed, truffle-flecked potatoes (Thanksgiving with a Tuscan twist), all washed down with glasses of Brunello, made from grapes visible just through the window. We finish with a crunchy hazelnut gelato topped with — you guessed it — truffles (it works).

As the meal concludes, we're briefly joined by Berni's father, Gianfranco, who, in his 70s, is ruddy and robust and still a very active tartufaio, or truffle hunter (in fact, he heads the local truffle hunter's association). He stops for a brief chat, but soon enough, he heads out, in search of this elusive, enchanting food.

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