Best Historical Sites in Tuscany
Credit: Andrea Wyner

Trying to name five of the best sites of history in Tuscany is like trying to pick out the five best trees in a vast forest. Known Tuscan history began with the Villanovans around 1,000 B.C., followed by the Etruscans, then Romans, then by the Holy Roman Empire, then by the Middle Ages, and on to the Renaissance. All of them left a myriad of structures and works of art, one more fascinating—and in the case of the Etruscans, more mysterious—than the next. A visit to the most impressive site of each period, will give the visitor a deep understanding of why modern Tuscany is as it is, because every period left its indelible mark. And by mark, I mean something far beyond the mere physical such as the Etruscan necropoli (actual cities of the dead), or the Roman amphitheaters, or the medieval churches, or the Renaissance palaces. I mean the cities, towns, and the countryside, and through them, the Tuscan way of life: that certain way of looking at and enjoying daily life.

Of the hundreds of visitors who stop by each year at our winery, few comment on the marvelous Abbey of Sant’Antimo or Brunelleschi’s astounding dome, but almost all are left speechless by the magnificence of the manmade countryside (vineyards, fields, olive groves, farmhouses) the hamlets, and medieval towns, the gentle pace and friendliness of the people, and last but not least, the amazing food and wine. So here in chronological order, are the five sites, which will not only impress most, but also help in weaving 3,000 years into a continuum.

Populonia (Etruscan)

Let’s start with this ancient site of the Etruscans—and even pre-Etruscans—found behind a beautiful promontory off the Tuscan coast. It would be a pretty place to visit (the Etruscans had a great eye for gorgeous real estate) even if there were no historical ruins, but there are, in spades. The ancient port where hematite from the Island of Elba was made into iron, is now an archeological park containing a stunning necropolis carved into the cliffs, and some intriguing freestanding tombs that changed in design and execution through the centuries before the Romans. The experimental part has demonstrations in ancient crafting of daily goods. Do set a whole morning or afternoon aside; there’s walking involved if you want to do it right. Be sure to check the hours of operation, for this is Italy where few things happen the same way—or the same hour—twice.

Cosa (Roman)

While admittedly the single most impressive Roman structure in Tuscany is the theater of Fiesole 5 miles north of Florence that’s still in use today, the silent, glorious hilltop of Cosa with unlimited views up and down the coast and to the Argentario Peninsula, is one of the most stunning and rarely visited of Roman sites. The Romans used subjugated Etruscan craftsmen to build the town—the perimeter wall, still intact, is as impressive in the sizes and fits of the stones as any of the Incas’. The town layout gives a ready glance into Roman daily life. The small archeological museum is a gem, and near it are the remnants of an elegant, multi-leveled Roman villa. At the tip of the promontory, stand the ruins of a medieval castle (some walls and the prison pits still intact) built by the Aldobrandschis in 1269 and destroyed by the Siena in 1329. Be warned: there is no food nearby so pack a feast of a lunch. The ancient olive grove alone is worth the trip.

Abbazia di Sant’Antimo (Medieval)

Built of dramatically white travertine and alabaster and standing below green hills, this elegant Romanesque church gained fame when, in 781, Charlemagne placed his seal on the foundation. It became in effect an imperial abbey of the Holy Roman Empire when his son showered it with gifts and privileges. In the new millennium the power of the abbey was enormous, having jurisdiction over almost 200 castles, churches, hospitals, abbeys, mills and large farmhouses.

The abbey is simplicity and power embodied. Without interior decoration, it is a stark wonder. Still a working abbey with monks in long white robes holding daily mass in Gregorian chant, it is a visual and acoustic wonder, that gives us living insight into past monastic life.

Just above the abbey is the hill town of Castelnuovo dell’Abate, little changed for hundreds of years. The two sites together—the views all around are alone worth the visit—give us a good sense of medieval Tuscan times.

Siena (High Medieval)

I can’t imagine a greater contrast to the austere medieval Abbey of Sant’Antimo than the gingerbread, birthday cake, glitzy, high-Gothic Duomo of Siena that began construction in the twelfth century. Its west façade alone is a rampage of arches and triangles, portals, columns, spires, gargoyles, sculptures of saints, alternating stripes of green and pink marble, mosaics and gold. The interior? Fogetaboudit. Every square inch of wall and ceiling—not to mention the 56 magnificent marble panels of the inlaid floor—is carved, frescoed, polychromed or gilded. It’s a visual orgy. While Sant’Antimo inspires calm and introspection, the Duomo razzle-dazzles in a freewheeling flaunting of the wealth of its merchants and bankers, who, without restraint, competed with rival Florence.

While the Duomo is overwhelming, even gaudy at first glance, its individual works—from the marble pulpit, to the choir stalls, to a couple of Donatello’s sculptures—looked at one at a time, are for the most part quiet masterpieces.

To complete your amazement by Sienese grandiosity, do visit Il Campo. It is the world’s most welcoming town square: fan-shaped and concave, it practically cuddles you. It is flanked by the graceful Torre di Manga, a mere 286-feet high that you should climb to give you a complete understanding of the layout of—after Venice—Italy’s most romantic city.

Florence (Renaissance)

To fill your eyes with wonder made by man, there is simply no Tuscan place like Florence. It is of course in almost every church and palazzo you see, from Brunelleschi’s dome (1420) and the Church of San Lorenzo, to the elegant loggia and tower (twenty-three feet taller than that of Siena) in Piazza della Signoria.

But the Renaissance in Florence began on a much smaller scale, namely with a sculpture by Nanni (died 1421), the Coronati, whose lifelike and agonized heads recall Roman sculpture. The passion for the human body of Donatello (born 1386) was the true rebirth. His earliest signed work, the bewildered Zuccone is so lifelike that legend has it Donatello shouted at him, “Speak, speak, or the plague take you!” His life-size bronze David (modeled after a delicate, soft-bodied adolescent) was the first freestanding nude statue since antiquity. Another of his life-sized statues, Mary Magdalene—this time in wood—is so emaciated and tortured, that her internal torment seems to have taken physical form. In emotional contrast, Luca Della Robbia’s Trumpet Players (1435), with its chubby and charming cherubic kids, is an expression of pure human joy. In painting, the celebration of the human physique and human vivacity was given life by Botticelli in his Spring (1482) and Birth of Venus. Innocent yet full of lust, they revel in the true rebirth: that of the human spirit.