Castles of Tuscany: A Regal Excursion from Florence

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Chianti, extra-virgin olive oil, balsamic vinegar, and history lessons, too.

“Life wasn’t always so peaceful in these beautiful hills,” says Alessandro, our tour guide, though it’s difficult to imagine any kind of unrest as we look out over the orderly rows of grapevines and stately cypress trees that line the serene Tuscan countryside. He is filling us in on the area’s turbulent history as we head out to visit medieval castles and taste the wines of their vineyards.  

The first stop on our small-group City Wonders tour is Castello di Verrazzano in Greve, birthplace of Giovanni da Verrazzano, the first European to discover New York Bay and much of the east coast of North America. (The Verrazano Narrows Bridge that joins the New York City boroughs of Brooklyn and Staten Island—incorrectly spelled with only one z, for now—was named in his honor when it opened in 1964.)

Walking through the landscaped grounds surrounding the castle, we hear roosters crowing, and we learn that the black roosters, which we now glimpse through a fence, are the symbol of Chianti Classico, the high quality wine of Tuscany. Further on, we are able to see—at a safe distance—the farm’s family of wild boars (cinghiale, in Italian) as they roam the hills below the castle grounds.


Courtesy City Wonders

Inside the castle, we are guided through cool, damp cellars housing oak barrels of aging wine, and we inhale the musty aroma of wood and fermenting grapes. Through a gate, we peer into a small room filled with dust-covered wine bottles, some stacked on shelves, some sitting on the floor, all so thickly covered in gray that the labels are barely visible. “They are the history of our winery,” our guide tells us. “Not for drinking, of course.”

We move on to another room where we see just a few labeled wine barrels and tall wooden racks. We learn they are awaiting grapes which will hang for about three months until their sugars become concentrated and ready to be pressed into lush, sweet Vin Santo. This limited-production dessert wine, with its amber color and complex, honeyed taste, is often served with cantucci, small biscotti, for a sweet ending to dinner.


Courtesy City Wonders

Next, we gather around a table in a large, sunlit room anticipating our tastes of the estate-produced olive oil, balsamic vinegar, and Chianti. First, the olive oil. Our hostess explains that the bread we are served is made without salt, so we are welcome to add some as we taste.  

Tuscan bread’s lack of salt, we are told, dates back to Florence’s rivalry with Pisa, the province that controlled salt from the sea. We’re learning more about those ancient rivalries and how today’s Italy has evolved from its complicated past. We taste the extra-virgin olive oil, and it is bitter, peppery with a little burning sensation, and fresh.  

Our hostess then serves each of us a small spoonful of dark, syrupy balsamic vinegar to sample. Small pieces of Pecorino Romano are passed around; the crisp, salty cheese is a delicious combination with the sweet balsamic vinegar. Aged for many years in wood barrels, this grape product becomes dense, complex, and luscious. We are happy to hear that both the olive oil and balsamic vinegar, along with the wines we would soon taste, are available for purchase later.

On to the Chianti tasting. First, we taste the Chianti Classico: a rich, deep red with a bit of tannin, according to the experienced palates in our group. Next, we have the privilege of tasting the Riserva, a specialty made only in the best vintages—a richer, smoother, more complex wine.  We see Giovanni da Verrazzano’s bearded face on each of the Chianti bottles and agree that he would approve of the wines that bear his name.

Almost simultaneously, we all sit back and sigh with the pleasure of enjoying extraordinary wines in a beautiful setting. But our driver awaits, and we are soon on the road and looking forward to our next stop. It’s time for lunch and some free time to explore the small town of Greve in Chianti. There, a wide piazza is surrounded by restaurants and shops with a monument to Verrazzano in full armor as a centerpiece.


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Alessandro suggests a visit to Antica Macelleria Falorni, a butcher shop and restaurant serving everything from soups, panini, and steak tartare to coffee and ice cream. Prosciutto, salami, hams, strings of garlic and peppers, and even hindquarters of wild boar (hair still intact) hang from the ceiling. An entire room is filled with cheeses and their earthy aromas. We watch a butcher patiently prepare a chicken skin stuffed with several types of meat, topped with sage leaves and a thick slice of bacon. When we ask about it, he points to a completed version, neatly tied with perfectly spaced rows of twine. We all wish this was our neighborhood butcher shop.

As we approach the Castello di Brolio in Gaiole, we are greeted by the majestic red brick structure overlooking more meticulously planted rows of grapevines. The walled estate encompasses nearly 3,000 acres of hills, valleys, woods, and olive groves, with 600 acres devoted to vineyards and farmland. When we reach the castle’s hilltop location, Alessandro points in the distance to the city of Siena, for centuries its powerful enemy.  

The well-fortified castle has survived many attacks through the years, not only from Siena’s armies, but also from the Spaniards and others as recently as World War II. We examine scars from those bombardments, still visible on a castle wall.

This castle is considered to be the birthplace of Chianti, for in 1872, Baron Bettino Ricasoli created the first modern “recipe” for the wine, specifying the Sangiovese grape as the primary component of Chianti. We look up at Ricasoli’s former balcony—his family has owned the castle since 1141 and still occupies part of the estate. In addition to his role in farming and viticulture, Ricasoli was an important political leader and Italy’s second prime minister. We tasted the winery’s specialties before Alessandro gathered us to prepare for our return to Florence.

While driving the roads through Tuscany can be fun on your own, joining a tour allowed us the freedom to enjoy the views from the comfort of an air-conditioned coach with no worries about directions, parking, or sipping Chianti. It didn’t hurt that we were led by someone as knowledgeable as Alessandro, the son of a chef, and a well-trained student of history and wine.

After our day of walking through castles, sampling wines, and getting to know one another, we welcomed our comfortable seat and a nap on the way back to Florence. Alessandro considerately turned off his microphone as we drifted off into dreams of medieval battles and vine-covered hills.

If You Go

City Wonders:  Specializing in small groups, exclusive access, and exceptional guides, City Wonders offers this tour and many others in Florence, Rome, Venice, London, and Paris.   Florence tours include convenient “skip the line” museum entry, vineyard dinner and wine tastings, and a full-day trip to Cinque Terre. citywonders.com

Castello di Verrazzano, Greve in Chianti: Should you fall in love with the castle during your tour, you might want to spend a few nights in their Foresteria Casanova, a recently restored farmhouse in the midst of the vineyards. The Hosteria restaurant provides traditional rustic Tuscan meals created from the farm’s products. Double rooms start at around $100 per day, and breakfast is included with the first night’s stay. verrazzano.com


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Castello di Brolio, Gaiole in Chianti:  Agresto, a restored 18th-century farmhouse on a hill surrounded by the estate’s vineyards, offers privacy and panoramic views. The four-bedroom home has a large living room, an outdoor patio area, and pool. The Osteria del Castello restaurant serves Tuscan-style meals from April through October. Agresto is available with a two-night minimum stay (and a one-week minimum during July and August). Contact via website for rates and availability. ricasoli.it

Antica Macelleria Falorni, Greve in Chianti: This butcher shop should not be missed if you’re traveling through the Chianti region, even if just to see the hanging prosciutto, salami, and hams and sample their cheeses. They offer an extensive eat-in menu including wines and desserts, but you’ll also want to take some cheese, wine, or cured meats with you when you leave. Mail order is available too. falorni.it

Hotel Helvetia-Bristol, Florence: The old-world décor and ambiance of this conveniently-located hotel is a perfect place to experience the charm of Florence and to start your exploration of Tuscany. Sitting before the fireplace surrounded by antiques, you’ll feel as if you’re in the living room of an 18th-century villa. A full buffet breakfast is available. Cocktails and meals are served in an elegant setting, and patio tables overlooking the Piazza Strozzi are available as well.  Double rooms start at around $600. hotelhelvetiabristol.com