Nothing says Italy quite like the soft, rolling hills of Chianti, and a long weekend spent winding along the valleys and vineyards of this world-renowned paradise in search of its history and flavors can satiate both body and mind. From Machiavelli to Lorenzo the Magnificent to the storied Medici, a few days spent exploring enchanting castles and noble villas once the sites of some of history’s most intriguing figures is time well spent. Wander through the picturesque tiny towns once the heart of the Italian Renaissance that evoke a culture which has influenced century after century and inspired artists and writers the world over. Here vineyards flow into olive groves and lead the casual visitor to wineries and restaurants brimming with some of Italy’s most famous wines and dishes. Follow along for a little taste of Tuscany’s natural and historic splendor. It’s a weekend in the heart of Chianti exploring a couple of its charming villas and castles where visitors can stay, relax, eat and drink.
Surrounded by the bright green of the hills outside of Florence is Santa Brigida, a small town near Pontassieve, dominated by the Castle of Trebbio famous for the family which once owned it – the Pazzi. This family became known in history as the arch enemies of the Medici family. Local tradition would have it that the plot to bring down the Medici and kill Lorenzo the Magnificent‘s brother, Giuliano, was hatched up within the walls of this very castle in 1478.
Today, all of the splendors of this historic location can be explored by visitors, including a look at the Pazzi family crest, designed by Donatello, located in the courtyard. For the past eighteen years the castle has been owned by the Baj Macario family. The family’s love for the building and its rich history lead them to carefully renovate the castle to restore its original beauty, while cultivating the estate’s 350 hectares filled with vineyards and olive groves.
Castello del Trebbio is also a renowned producer of many celebrated wines including one series of labels dedicated to the infamous anti-Medici plot: Pazzesco, made from a blend of Merlot and Syrah; La Congiura (the plot) a blend of Riesling and Pino Grigio; De Pazzi a particular blend of Sangiovese, Merlot and Syrah aged in amphorae.
Castello del Trebbio boasts an extensive wine cellar tucked away behind a cast iron gate in the castle’s restaurant La Sosta del Gusto. Over 100 of the finest wines await to be uncorked including Chianti Rufina. The restaurant itself is located in an ancient cellar and exudes an atmosphere that is at once rustic and elegant. Head chef of the restaurant, Claudio Vignali, prepares dishes perfectly matched to the vast offerings of the wine cellar using local products along with olive oil and saffron straight from the grounds of the estate. The heavenly combination of exquisite food and excellent service under the vaulted ceiling of the restaurant are truly a Tuscan dream. Taste the breast of guinea-hen in Vinsanto or the handmade pasta, straccio verde, with boar ragù. When visiting the castle between the months of October and November, visitors can tour the olive groves and taste the olive oil selected for production by owner and official taster of olive oil for the Florence Chamber or Commerce, Anna Baj Macario.
Castello del Trebbio is also home to a cooking school where visitors can learn to make homemade pastas and crostini in one of the estate’s kitchens. Guests choosing to spend a bit more time at the castle and to explore the area can rent one of the elegantly appointed apartments or villas located in the renovated castle or on its grounds. Tours of the castle (including a peek at its dungeon), the winery and the olive groves and production areas are available daily and last for about an hour. At the end of the tour a wine tasting is offered pairing the wines with fettunta (toasted bread drizzled with homemade olive oil) served with Tuscan salami and pecorino cheese.
Heading south through the gentle Arcetri hills is Villa Le Piazzole, a villa which in the 1400s was the summer estate of the powerful Florentine family, the Acciaiuoli. The beauty and elegance of the villa is breathtaking as are the typical Italian gardens surrounding it. The villa’s facade dates back to the 16th century and one step inside is as if stepping into history while still enjoying every imaginable modern luxury a traveler expects. Wandering through to one of the terraces visitors will discover magnificent views over the green countryside. Don’t miss an afternoon stroll amongst the olive groves and through the vineyards at times accompanied by the sighting of one of the pheasants, hare or deer which call the gardens their home.
The villa is located on an estate covered with vineyards and olive trees, making it of no surprise that here some of Tuscany’s best olive oil and wines are produced using traditional, natural methods of production. Stop here to taste Villa Le Piazzole Rosso Toscana a full-bodied IGT (geographically classified wine) a blend of Sangiovese, Cabernet Sauvignon and Merlot that bursts with intense color and harmonious structure. For those preferring to taste a white, try Il Giardino de Le Piazzole, a blend of Chardonnay, Pinot, Trebbiano and Grechetto. This white is velvety and intense with notes of vanilla. Tastings are held in the property’s wine cellar, Cantina della Torre, or alongside the crystal blue swimming pool. Wine and olive oil tasting tours can also end with lunches or dinners served on one of the terraces surrounded by the Italian gardens with a chance to relax and enjoy a juicy Florentine steak, a hot pizza fresh from the ancient wood oven or one of a number of other dishes offered here.
Continuing on through the heart of the Chianti Classico region weekend visitors will come upon Passignano located on the rolling hills which are gently caressed by soft breezes. The heart of the town is the ancient village Fonte de Medici, which for twenty-six generations has remained at the heart of the Antinori family where they produce several highly prized wines, Tignanello and Solaia. The village itself gets its name from a tiny fountain used as a resting place for pilgrims traveling south towards Rome. The estate extends across two small hills, Santa Maria a Macerata, where visitors will find the hotel’s reception, spa, several rental apartments and the restaurant La Trattoria della Fonte, and the other hill is known as Tignanello where other apartments are available for rent and are surrounded by vineyards. With edifices dating back to the 1400s, the picturesque hotel and apartments display the distinct eye for tasteful furnishings and attentive hospitality which its owners are so proud of.
Just a short distance from here, visitors can go inside the abbey, built in 395 by the Archbishop of Florence, called Badia di Passignano. Today this old building is home to 2000 barriques used by the Antinori family for aging their Badia a Passignano Chianti Classico Riserva. This stunning red pairs beautifully with steak, salami and pecorino. Tours and tastings are available daily.
After a visit to see the barriques, stop at the acclaimed Osteria di Passignano for a modern take on traditional local cuisine, where every dish is made using locally produced products and stone-ground organic wheat. Taste crostine with red cabbage and beans, or linguine with homemade lamb ragù with baby asparagus, and roast pigeon breast with fennel and orange. The restaurant lavishes its clientele with a great sense of detail which is notable in the tables, paintings and of course in its dishes, such as ricotta ravioli with pork ragù, a grilled cheese platter with seasonal vegetables and its lists of handmade pastas and local meats. Owners Marcello Crini and Allegra Antinori carefully select the vintages and best labels for their wine list includes everything from reds and whites to rosè and spumanti. If dinner guests can’t imagine leaving these exquisite flavors in Tuscany once they head home, they can sign up for cooking classes held by chefs from the Fonte de Medici who will teach about the secrets of good Tuscan cuisine.
Driving on just a bit further, travelers can stay at Niccolò Machiavelli’s countryside residence at Castello di Bibbione. Bought by the infamous Italian Renaissance historian, humanist, philosopher and politician in 1511, the castle conserves a secret underground passage which curves underneath the building for hundreds of meters until it opens to the shores of the River Pesa. The lands surrounding the castle are dotted with olive trees, vineyards and sunflowers. Guest rooms are located in the restored farmhouse and still offer visitors the beauty of their antique terracotta floors, stone walls, wood beamed ceilings and fireplaces. Guests can also enjoy the spa and pool with its gorgeous panorama.
The olive groves surrounding the estate are used to produce extra virgin olive oil, Marchesi Rangoni Machiavelli. Every olive is painstakingly handpicked and the oil remains a bright green with the typical flavor Tuscan oil is noted for. The Vinsanto del Chianti classico Fattoria di Bibbione is a traditional dessert wine with a distinct amber color and intense, elegant flavor which is ideal served with the small, classic almond biscuits, Cantuccini di Prato.
For those who wish to delve even deeper into the unique tastes of Tuscany, the trip heads on to the towns of Greve and Panzano in Chianti. The first stop is in the small village of Greve for an aperitif, aperitivo, at the wine bar and shop Le Cantine di Greve in Chianti owned by the Antica Macelleria Falorni and opened in 1729 in the vaulted cellar of an old building. It is the largest wine cellar in Chianti and offers 1000 different wines for sale and 140 for tastings by the glass. Labels are from Tuscany, primarily Chianti Classico and some of the best wines from Montalcino and Super Tuscans from the coastal areas. Take advantage of the paper and pencils placed around the shop to allow customers to jot down tasting notes. Enjoy pairing your glass of wine with local cheeses, hams, finocchiona and Chianti Classico salami. Visitors can also buy over 20 types of Tuscan olive oil as well.
In Panzano make a quick detour at the butcher shop. Dario Ceccini, known as the most famous butcher in Italy, leads his guests to lively tables where they can tuck into daily offerings of various menus including dishes meant to be shared. The Menu del Macellaio di Solociccia comes with six servings of meat, seasonal vegetables, beans, local olive oil and includes coffee and dessert. With the Menu della Vacca Intera diners can also eat a typical bistecca alla Fiorentina.
For something dolce head to the old center of Prato where the small boutique pastry shop Il Nuovo Mondo, owned by Paolo Sacchetti, promises to cater to your sweet tooth. Sacchetti, who is vice president of of the Italian Pastry Academy, prepares his traditional Pesche di Prato, two round slices of brioche cake soaked in alchermes (an Italian liqueur with flavors of cinnamon, cloves and nutmeg) and scented with vanilla before being lightly filled with pastry cream and a candied orange to garnish. The final product, which looks like a juicy summer peach, is a unique Tuscan pleasure.
After having savored the flavors of the region, it’s time to look for a special object to bring home, something unique from the area. A few kilometers from Prato, heading in the direction of Arezzo, drive to the town of San Giovanni Valdarno and stop at IVV, l’Industria Vetraria Valdarnese, a shop filled with shimmering crystal. Take a look at the Home&Table line with its array of elegant designer pieces for the home ranging from glasses to candle holders, center pieces, vases and more.
The immense treasures of Tuscany cannot be discovered in one short weekend or even in a few days, but a glimpse of the magnificence of what it once was and all that it offers today is surely a journey to be cherished. With every trip a new side of what is one of Italy’s most well-known regions springs up. These few days spent traveling through its nature, castles, villas and estates, sipping on its wines and tasting its traditions is like opening a history book and stepping back into the Renaissance – for Tuscany is beauty, elegance and discovery.