The Romance of the Hunt

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This interview had me particularly excited because, as a truffle lover myself, I was eager to learn more about the real world and experience behind it. Taking my children truffle hunting is also high on my bucket list. Forget deep diving or swimming with sharks. There is something far more romantic and personal about walking into a Tuscan forest with a truffle hunter and his dog, searching for something precious hidden beneath the soil.

My conversation with Massimo Cucchiara unveiled that and much more. A third-generation tartufaio from San Miniato, Massimo grew up surrounded by truffles and the people who search for them. Today, he shares that tradition with travelers, not simply to offer an interesting experience, but to help them understand what a real truffle is and why the land that produces it needs to be protected.

Truffle hunting has become increasingly popular with visitors to Tuscany. Experiences are offered everywhere, sometimes even with the promise that guests will find truffles. Massimo does not make that promise. His version of the hunt remains faithful to the tradition he inherited: one hunter, one dog and no guarantee that the forest will reveal anything that day.

“The dream is to find the biggest truffle in the world every morning, but we don’t know,” he told me. Hunting for white truffles can mean spending six or seven hours walking through the rain and mud, carrying boots and an umbrella, and still returning with nothing. “We need to be a little bit crazy to go in the forest,” he added with a smile.

Perhaps that unpredictability is part of the romance. We live in a world in which almost everything can be booked, scheduled and delivered. Truffle hunting asks us to surrender control and enter the forest on its terms. You may find a magnificent white truffle, a tiny one or nothing at all, but the possibility keeps you watching the dog, reading the landscape and waiting for that sudden moment of discovery.

For the dog, Massimo explained, the hunt is a game. He begins training his dogs when they are puppies, and over time, they learn to understand one another. The dog recognizes the tone of his voice, while Massimo learns every shift in its body language. “In the end, after a few years, we speak the same language,” he said.

His 11-year-old dog, Mela, moves her tail like a flag when she begins to smell a truffle. If it moves too quickly, Massimo knows she has probably detected a rabbit or another animal. These are small signals that an inexperienced observer might never notice, but they reveal why a dog cannot simply be handed to a visitor and expected to lead the way. The dog also knows when the truffle is ripe. Because truffles grow entirely underground, this is essential not only for finding them, but for protecting their natural reproduction. A ripe truffle releases spores into the soil. When it is collected correctly and its habitat is left undisturbed, truffles can grow there again.

Massimo describes the moment when the dog begins to dig as a rush of emotion. He compared it to opening a Christmas present while secretly hoping to find a diamond inside, only to discover a pair of socks. You never know what is waiting beneath the soil, but it is those few seconds, after hours of searching, that bring the hunter back into the forest.

“The truffle hunter is a kid who has the dream of finding the biggest truffle in the world,” Massimo told me. That may be the most endearing way to understand the pursuit. Beneath the expertise, patience and years of accumulated knowledge, every hunter is still waiting for the forest to surprise him.

There was another revelation during our conversation, one that may disappoint fellow truffle lovers. Most truffle-flavored oils, butters, cheeses and sauces rely on chemical flavoring rather than the real ingredient. The overwhelming aroma many of us associate with truffles is often evidence that we are not experiencing the real thing at all.

A fresh truffle, Massimo explained, should be pleasant and delicate. “If you smell the real one, it makes you happy. You open your eyes, you smile. It’s like a flower,” he said. Even for the families who hunt them, truffles are not an everyday indulgence. They are reserved for special guests and special occasions, best enjoyed simply and with a genuine appreciation for what it took to bring them to the table.

Massimo’s favorite way to eat a white truffle could not be less pretentious: sliced over a fried egg. I love that something considered one of the world’s most luxurious ingredients is best understood through such a familiar dish. It says something about truffles themselves. Their value does not come from an elaborate presentation, but from their rarity, their connection to the land and the patient search behind every discovery.

San Miniato remains less internationally recognized for truffles than Alba, something Massimo attributes mainly to marketing. Yet the Tuscan town sits within an extraordinary landscape shaped by ancient marine soil, rolling hills and the Arno Valley. It is the same land that gives Tuscany its Sangiovese, Chianti and extra-virgin olive oil. For Massimo, these are not separate products but expressions of a territory that must be protected as a whole.

That responsibility has become more urgent as the number of truffle hunters has grown. When Massimo began accompanying his family into the forest approximately 40 years ago, there were perhaps 20 or 25 hunters in his area. Today, he estimates there are between 300 and 400. Not everyone enters with the same respect for the land, and careless digging can damage the habitat that allows truffles to return.

His grandfather taught him to respect the forest and remember that people are not alone there. Massimo is now passing those lessons to his youngest son, Alessandro. At seven years old, Alessandro found his first white truffle, the most difficult test for any hunter. The image of Massimo teaching his son what his grandfather once taught him may have been the most meaningful part of our conversation.

He also works with students, from primary-school children to university groups. Many arrive knowing only that their parents pay a great deal of money for truffles. By the end of the experience, after following the dog and seeing the connection between the ingredient and its habitat, they begin to understand that the true treasure is not only what they might uncover beneath the soil. It is the forest itself.

When I asked Massimo what every traveler should know before visiting Tuscany, he encouraged them to leave its celebrated cities and explore the countryside. Florence and Siena may be beautiful, but for him, the real Tuscany is found beyond them, among the hills, forests and people who continue to care for the land.

“If we preserve our land, we will continue to be Tuscany,” he told me. “Otherwise, that’s it.”

I began this conversation dreaming of the thrill of finding a truffle. I left it thinking about inheritance, patience and the quiet knowledge exchanged between a hunter and his dog, a father and his son, and one generation and the next. Truffle hunting may still be high on my family bucket list, but now I understand that the experience is not really about what we might find. It is about entering the forest with enough curiosity and respect to understand what has been there all along.

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Photo: Courtesy of Truffle in Tuscany

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Behind the Stay is an editorial series by The Curated Itinerary exploring the people whose leadership shapes some of the world's most memorable hotels. Through conversations with general managers, founders, and hospitality leaders, the series looks beyond the rooms and into the philosophies, decisions, and people that define exceptional stays.