Marathon of Meals

“Tartufo!,” exclaims Lucca. He saunters through the forest, bright blue eyes as crisp as the morning air and a mop of curly hair, channeling a blonde Slash from Guns N’ Roses, bounces toward us. Delicately cradled in his callused hand is a small yet pungent Tuscan truffle. His father, Luigi, the professional hunter of the bunch, only speaks Italian. With stern yet encouraging commands, Luigi leads Mora, a.k.a. Blackberry—a Labrador and Logotta Romagnolo mixed truffle-hunting dog through the Natural Reserve of Truffles, located roughly 10 miles from the tiny downtown of Certaldo. Though still hugged by rich Tuscan mud—it rained and snowed overnight—the marzo tartufo tempts one of our crew to eat straight from Lucca’s hand.

“Foodie” may be a nebulous term nowadays, but our group of four goes weak in the knees for this fancy fungi. As we walk south, tip-toeing the Tuscan woods and dutifully giving Luigi and Mora – who, we learn, fetches 8,000 euros as a trained truffle scout – space and silence, with every delicate truffle gifted, our coat pockets begin to bulge. Fittingly, our waist-lines, too, are quickly increasing in bounty on this trip. But no matter. We’re in Tuscany, visiting one of Exclusive Resorts’ five, four- to five-bedroom villas at the famous Castello di Casole, a Timbers Resort, in February to discover what off-season in the Italian hillside may reveal. And as any Tuscan traveler knows—foodie or not—we’re in the cradle, the mother lode, of food and wine. Our mission? Meals. Lots of them. We anxiously anticipate Mora’s next move, and as additional marzo truffles are unearthed from the rich Tuscan dirt, we “ohh” and “ahh” at this country’s abundance of culinary riches.

Volterra, Chianti + Cows

Though epicurean treasures are heralded in Italy, so is its storied past, as the country’s tumultuous history is celebrated with every hilltop village near Casole d’ Elsa, where the Club’s charming farmhouse residences and the 4,200-acre Castello di Casole hold court. In summer, given the resort’s sprawling Italian villas, private infinity pools, high-end restaurants, on-site vineyard, olive groves, and hiking trails, one is hard pressed to even leave the grounds. Come winter, though the resort’s Italian charm remains seductive, the nearby Tuscan hillside, a quilt of brown and green farmland, is sleepy and serene. This equals opportunity. With fewer Fiats of Chianti-happy tourists snaking through country roads, day trips to nearby towns are easier to navigate. From Castello di Casole, the towns of San Gimignano, Volterra, Siena, Certaldo, and the Chianti wine region, among other spectacular sites, are just an hour’s drive, give or take.

After a harried journey to Italy, unexpectedly ping-ponging through a staggering amount of European airports at the mercy of snow and fog, we eventually touch Italia terra firma. Once at Villa Barbena, our extended flight time is immediately rewarded with authentic Italian charm, and with the guidance of a stellar onsite concierge team (a bevy of in-the-know local minds), with every Tuscan dawn we find ourselves happily crammed into a tiny Audi, each day punching in different destinations on a finicky Italian GPS system. As we weave through the movie-set scene of cypress-lined resort roads, we keep our eyes peeled for cinghiale, or wild boar. And our San Francisco foodie announces a Tuscan truffle challenge: One meal a day must involve the truffles Luigi and Mora hunted for us. Carting the pricey finds in her purse, she means business.

During one of our first mornings, talk of an unusual Tuscan snowstorm is the local buzz. We fight jet lag with espresso and talk of the week’s menu. We decide on the town of Volterra for one of our first meals. Though not as famous as nearby San Gimignano, Volterra’s charm is nearly as impressive, with two main castles, several photo-worthy sculptures in the town square, and famous Etruscan tombs.

Perhaps most touted is the architecture of the city’s Cathedral (duomo) of Volterra. During the 19th century, the duomo’s interior was painted in stripes – typical of Tuscan church design – and its floors patterned with black-and-white marble. The result, a formidable church that, no matter the time of year, is filled with varying languages, as visitors pray or wonder aloud at the intricate design and hand-carved marble. After sightseeing, we stumble upon a tiny little restaurant, Le Grazie. Greeted by the owner, we descend several flights of stairs to a cellar table, where, in eclectic Volterra style, gnomes and toy wizards set the scene. Eccentric and absolutely foreign, this enoteca and our first Italian meal are notable, as it sets the pace for a marathon of meals: a dizzying array of local pecorino, prosciutto, pasta, and Chianti so tasty that its modest price must be a mistake.

Our following day trip, however, proves that Chianti, and more specifically, Chianti Classico, is as rich in tradition as Volterra’s famous Porta all’Arco, the town’s original Etruscan entrance. Oenophiles may tout super Tuscans and big Brunellos, but Italy’s table wine is what first landed this stellar wine region on the map. Our San Francisco foodie has done her homework, insisting we visit the Monte Bernardi winery and estate located in Panzano—the pulse of the Chianti region. Owned and operated by brother-and-sister team Michael and Jennifer Schmelzer, this Tuscan outpost is a favorite among acclaimed American master sommelier (from Napa’s French Laundry and Boulder’s Frasca Food and Wine) Bobby Stuckey, who has collaborated with Schmelzer on wines for his Scarpetta portfolio. An off-season travel bonus is a private estate tour by Schmelzer himself, who shows us to his family’s charming farmhouse (rented by the week during high season) and its backyard treasure—idyllic rows of robust, old-world Italian vines.

Over a Monte Bernardi wine flight, we learn that to be deemed Chianti Classico DOCG—marked by the famous Chianti Classico rooster—the ratio must be at least 80 percent Sangiovese, the prominent grape of the region. At the 130-acre Monte Bernardi estate, Sangiovese is indeed the star, as Schmelzer cites the rocky soil as prime breeding ground for Chianti Classico. We crown the 2008 Sa’etta (Thunderbolt) DOCG as the favorite, a Chianti Classico Reserva crafted from 100 percent Sangiovese. Schmeler’s local recommendation for lunch in Panano? Officina Della Bistecca. “You must visit the butcher,” he insists.

The Butcher + The Vintner

If the big ceramic cow doesn’t suggest you’ve arrived (after wine tasting and windy roads, one’s own GPS can waver), simply follow your nose. Dario Doc and Officina Della Bistecca are both owned by famous chef and butcher Dario Cecchini. We enter through a tiny, street-level butcher shop and are quickly ushered upstairs for lunch at Officina Della Bistecca. A long communal table is shoulder-to-shoul-der with locals, and we’re the only guests speaking English. We forgo the menu and ask the grill chefs—who cook not three feet from the table—to surprise us.

Chef Dario’s spell is quickly cast: a course of raw vegetables from the garden dipped in simple, housemade olive oil. Chianti crudo, or beef tartare, and Carpaccio di culo, seared rump, served with super-sized capers. Next, bistecca Fiorentina so tasty we fight over the last bite, and an onslaught of sides: Tuscan beans and potatoes simply prepared with burro del chianti (Chianti butter) and profumo del Chianti (special salt). We sip from a carafe of vino di Vittorio, the restaurant’s handmade Chianti. As our beef is coaxed to perfection, one young chef builds a Leaning Tower of Pisa with shot glasses, vehicles for grappa. We toast the chefs and their hideaway of Italian culture and cuisine. After a two-hour feast, we top lunch with double shots of espresso, as duty still calls. Though we’ve experienced the talent of this famous Tuscan butcher, we’re off to meet a winemaker whose reputation is equally as intriguing.

Though the hilltop perch of Castello di Casole commands extraordinary, postcard-perfect vistas – the area’s origins date back to the Bronze Age, 3000 B.C., and the hotel’s namesake castle underwent a major renovation during the 18th century prior to a Timbers Resorts makeover in 2005—the entrance to the property is where its famous terroir is bottled and preserved. Castello di Casole winemaker and oenologist Paolo Caciorgna lives just a stone’s throw from his Macchie (“forest” in Italian) vineyard. Young, gracious, and one of Tuscany’s most notable vintners, Caciorgna greets us at his wine cellar with a wide smile and a bottle of Macchie DOC Sangiovese Terre di Casole. We walk the small vineyard and winery, built in 2010, before tucking into his tasting room. More formaggi e salumi (the best thus far, crafted from a friend of Caciorgna’s), more prosciutto. But the wine? So tasty we quickly sign up to ship cases of his Alberaia IGT Toscana, a 100-percent Sangiovese, and Macchie Passito, home.

Blizzard or Bust: Siena + San Gimignano

During high season, Siena teems with tourists, and for good reason. Deemed a UNESCO World Heritage Site, the famous Piazza del Campo and Mangia Tower lure visitors from all corners of the globe. Come February, however, the fabled crooked streets and town square, home to the Palio, an exciting bi-annual horse race, are buzzing with locals. The farmer’s market is robust and rowdy, covering nearly four downtown blocks. The flower stand – a brilliant maze of roses, hydrangeas, and lilies – demands a long pause. As does a local goat cheese vendor as we clamor for samples. The local weekday crowd is on a mission. Smartphones, nearly nonexistent. Rather, the barks of bargaining. Italian leather goods are a given, including one of the largest shoe collections in Italy. Families and dogs roam the market, a tiny Pomeranian dressed in red, green and white socks struts by. “Viva Italia!” shouts an older gent, winking at its owner.

Though sampling these farm-to-table goods could almost serve as lunch, a challenge to off-season travel is, on this day at least, a bitter winter chill. We scurry for cover at Osteria Le Logge restaurant. Tables are presided by decorative shelves of Italian history and weathered recipe books. We start with local meats, cheeses, and wine. But the pasta? Oh my. Spaghetti noodles so long we twist them nearly two feet above the plate. Soft, succulent pillows of ravioli that cause a table of four women to go silent. Mirto, the manager, opens a 2013 “baby Brunello,” he says. “I call this wine sexy, kind of like Italy.” After lunch and a brief history lesson on Siena, which includes a book from the restaurant’s shelves signed by American politicians and Italian aristocrats, he walks us to the latest outpost by Le Logge’s owners, Un Tubo, a wine bar filled with 200-year old Etruscan tombs and multiple cellars of Italian reds dusty with age.

And if every medieval hilltop village has their own tale to tell, San Gimignano, a smaller town located in the province of Siena, perhaps most proudly displays its storied past. Coined the Town of Fine Towers, this gorgeous Italian village has an unforgettable skyline of preserved towers. Two main churches feature artwork by Italian Renaissance masters, and streets are lined with charming espresso bars, meat and cheese boutiques, and corner cafes. The Musei Civici includes the Archaeological Museum, exhibiting the city’s origins, the Pharmacy of Santa Fina, which displays ancient medicinal preparations, and The Gallery of Modern and Contemporary Art Raffaele De Grada. And in contrast to several of its neighboring towns noted for red wine production, San Gimignano is known for whites, the Vernaccia grape grown throughout its sandstone hillsides. After touring its historic center (also a UNESCO site), we refuel at La Mandragola, a charming cafe. Here, the trip’s top truffle dish is crowned—linguini with chicken, truffle, and ham, paired with a local San Gimignano pinot grigio. Though tempted to order seconds of the truffle pate, we restrain, as evening plans include a visit to the nearby Fattoria Poggio Alloro for a farmhouse dinner.

Located just five kilometers from San Gimignano, this organic agriturismo, one of many in Tuscany, is perhaps the most well known. Bought in 1972 by the three Fioroni brothers, who worked the land prior to purchase, the farm has remained in the family. Dotted by vineyards, cereal crops, beehives, olive groves, fruit trees, and saffron, the land is bountiful. The main draw, however, is a herd of 50 Chianina beef cattle, one of the oldest breeds on the globe.

After being shown to the kitchen and small farmhouse dining room, we sit at another lively communal table and glimpse the main act of tonight’s meal: A marbled, Flintstone-sized raw steak to serve the entire room is displayed by the open grill, awaiting the hands of legendary 80-year-old Fattoria Poggio Alloro owner and chef, Amico Fioroni. Managed by his executive chef daughter and sommelier, Sarah Fioroni (author of cookbook A Family Farm in Tuscany), this multi-generational operation welcomes diners like family. We’re joined by local Italians, a couple from New England, and two feisty Jack Russell terrier pups named Cappuccino and Luigi.

We ask Sarah if she can cook us a dish with the truffles we’ve brought. Wish granted, 10 minutes later a special appetizer course of organic fried eggs and shaved truffle arrives, followed by Tuscan Ribollita soup, pappa al pomodoro, homemade risotto, and wild boar. Finally, the Florentine steak, served only on Saturday nights. Beef so tasty and tender that the room applauds; one guest gives a standing ovation. Here, Tuscany’s seduction is simple and confident.

Take Me to Firenze & Truffle Smuggling

But back to the truffles.

On the day we hunt with Lucca and Luigi, post-forest foraging, we follow Lucca to the town of Certaldo. The tiniest of the Tuscany towns visited, he proudly points to poet Giovanni Boccaccio’s (who penned Vita di Dante and Decameron) house, a 14th century facade that inspires movie sets. He walks us to his Mom’s kitchen, formally titled Cucina Giuseppina, an Italian cooking school so charming that we can’t stop snapping photos. Giuseppina is every bit the no-nonsense Italian cook. She shaves truffles while Lucca serves red wine crafted by his own hands—his riserva Chianti named “The Poet.” His father’s truffle bounty is the anchor to a three-course meal of meats, cheeses, eggs, and dessert. This is true farm-to-table dining, shared with a proud Italian family. We most likely overstay our welcome, and shopping bags are lined with kitchen utensils, olive-wood cutting boards, Lucca’s reserve wine, house-made jalapeno jam, and local olive oil. Desperate to hold onto this memory, they all help us carry a little piece of Certaldo home.

Truffle Reduxe

Not all of the truffles are cooked by Giuseppina. Our purses harbor the remaining goods and we can’t seem to part with the pungent gems. The “epic” snowstorm did fall—six inches of fresh powder cast a magical spell over the Tuscan hills, and ultimately slowed the Italian pace even further. Winemakers had more time to chat and chefs had extra time to cook made-to-order comfort food inspired by our own truffle hunt.

Our vacation comes to a close, and we stay overnight in Florence. After a dusk ascent up the famed Florence Duomo and a can-you-believe-how-lucky-we-are view, at dinner we ask one last chef if he would cook our truffles (too busy, but a meal at Il Santo Bevitore is a must). It’s decided we’ll just take the remainder home. We Google “flying with truffles.” Conflicting reports, so we go for it anyway. We land in the U.S., and our Aspen foodie giggles as she makes it through customs.

As we await our last leg home, half jokingly, we order Parmesan, prosciutto, and pinot grigio at the airport wine bar. Not quite the same experience. Tuscany is already slipping away. Yet we toast our truffle victory. We toast the little towns of Italy. We toast the once-every-10-years snowstorm. Our U.S. customs photos become fodder for jokes by family and friends. Harried mug shots are evidence of hard-earned pounds, jet lag, and serious sleep deficit. But now, with a few more cracks in our own armor, we, just like Tuscany’s streets, can claim a few Italian stories of our own.