Secrets of the Boot

Anna Ceraldi |

 Tucked a stone's throw away from the tiny town of Panicale, La Querciolana is a hidden treasure complete with its own historical church built in the 1400s on the site of a shrine to the Virgin Mary.

Nothing jump-starts the senses faster than day-dreaming of an Italian vacation. It's impossible not to conjure up images of golden afternoons lingering on a vine-covered terrace, sipping a rich Amarone and dreaming of your next meal. When planning a trip, why not immerse yourself fully in the Italian culture and live la dolce vita at one of the many agriturismos scattered throughout the Tuscan and Umbrian countryside?

The word “agriturismo” is derived from the Italian words for agriculture and tourism, which basically translates to vacationing in restored farmhouses, monasteries, and villas that also serve as working farms. In addition to all the benefits of a hotel room or furnished apartment, you can embrace the DIY spirit by participating in grape harvests, joining in the annual olive-picking, learning to cook traditional dishes in on-site kitchens, or whipping up a meal in your own cucina using meat and produce grown or raised on the property. Here are some highlights from my visit:




Perched high on a stunning hilltop in a 1,000-year-old hamlet between Siena and San Gimignano, Montecastelli is steeped in history—not to mention beautiful surroundings. Located on the famous ancient pilgrim road known as La Francigena, this lovingly restored villa was originally a walled castle; it was turned into a Benedictine monastery in the 12th century for more contemplative and less militaristic pursuits. Owners Jens and Ruth Schmidt managed to preserve the authentic integrity of the building while bringing modern-day luxuries into Montecastelli's four spacious, fully equipped apartments—each named after a variety of olive grown on the property. Boasting an impressive wine cellar and indubitably indulgent meals, Montecastelli is heaven for the veritable gastronome. 

Food Features:

Grand Chef Cooking Classes :: “La Scuola di Cucina con Chef Lazarro Cimadoro”
Discover six different ways to cook with olive oil (produced on the property) or perfect the fine art of pasta-making in one-on-one cooking classes with Chef Lazarro in Montecastelli's state-of-the-art kitchen. For more intensive training, five-day classes are available complete with multiple-course menu planning.

Wine Tours/Tasting

Tours of Chianti Classico, Montalcino, and San Gimignano. A four-hour tasting of 12 wines, including Sangiovese, indigenous varieties, and wines of the South.

Recreation Features:

Mountain Biking 

Fabulous trails in the Montagnola Nature Reserve behind Montecastelli


The Olympic pool in nearby Colle Val D'Elsa offers a wonderfully relaxing experience 

Day Trips to Florence and Siena


Agriturismo Cretaiole


Located in the center of Tuscany's stunning Val D'Orcia just a few miles from the beautiful town of Pienza, Agriturismo Cretaiole is run by the wonderfully hospitable Moricciani family. In renovating the 14th century farmhouse, the family has preserved unique architectural features while furnishing each of the six apartments with all the modern amenities. Guests have access to produce and meats from the family's 70-hectare farm, including pork, chicken, eggs, rabbit, and fresh vegetables from the garden. Exquisite olive oil is also available, produced from the land's 900 olive trees, some more than 500 years old. If you're interested in a cooking lesson, Isabella Moricciani is happy to share family secrets while leading the traditional pici pasta-making classes. The most important Tuscan lesson of all: "Simplicity makes miracles.”



Pasta-Making Classes

Grape Harvest and Olive-Picking

Visit to Olive Press

Truffle Digging

Wine Tasting in nearby Montalcino (Brunello and Nobile labels)

Hiking and Mountain Biking

Private Tour of the Hermitage of Pienza, owned by the Moricciani family


La Querciolana


Umbria is Tuscany's tranquil neighbor, located directly south on Italy's boot. It's a region lush with forests and medieval hill towns renowned for their rich history. Tucked a stone's throw away from the tiny town of Panicale, La Querciolana is a hidden treasure complete with its own historical church built in the 1400s on the site of a shrine to the Virgin Mary. Guests are free to visit; frescoes created by Piero della Francesca and local legend Perugino abound. The completely restored convent offers apartments with fully equipped kitchens and tasteful décor. Where else is it possible to sleep in a room used by a pope almost 500 years earlier? (Pope Paul III slept in the apartment beside the small church several times in the early to mid-1500s.) The accompanying working vineyard and farm produces its own award-winning olive oil, homemade prosciutto, and exquisite wine—including the superb Grifo di Boldrino, Rosso Riserva. The hospitality and excellent cuisine of Hostess Maria Luisa make a visit to La Querciolana well worth the trip.



Tennis Courts

Swimming (Pool features a vanishing edge overlooking vineyards)
Horseback Riding

Hiking Trails

Golfing at the nearby Lamborghini family estate

Wine Tasting for up to 20 people

Full Meal Service