5 Best Locations in Tuscany

Why is Tuscany on almost everyone’s bucket list? What is it about wandering around from hill town to hill town in Tuscany, passing through vast stretches of lush vineyards, that has such universal appeal? Why would you want to visit this idyllic part of the world yourself? And where should you go first in your wanderings?

To start with, Tuscany is steeped in history, dating back to the Etruscans in 900 BC, moving forward through Roman times to the contentious, art-enthused city states of the Middle Ages and Renaissance. Even today, the well-preserved towns and cities of Tuscany retain much of the charm and flavor of their pasts, offering a time machine of first-hand experiences of days gone by. From Etruscan to Medieval to Renaissance to modern times, Tuscany has kept its own unique version of timelessness, all proudly displayed in its museums and churches, but, in equal measure, evidenced in the “living museum” of its streets and piazzas, buildings and art.

And speaking of art… Tuscany holds one of the greatest accumulations of art in the world–with the masterpieces of Michelangelo, Botticelli, Leonardo da Vinci and many others–bringing its history to life, illuminated through art and sculpture.

Add to this the over-the-top, built-to-impress, architecture of its colossally extravagant cathedrals, with multicolored marble façades, inlaid marble floors that took centuries to complete, and soaring domes that were their own miracles of design at the time they were built. As if any further embellishment could possibly be needed, these massive edifices hold numerous masterworks of sculpture, fresco and stained glass, all joining together in an obvious attempt to inspire awe in the populace and humble them into obedience.

Equally appealing are the characteristic experiences to be enjoyed throughout the region, in each Tuscan town or city, large or small. The excellent wine, locally produced… The delectable food… The excitement of the piazzas, spacious centers of living filled with people and bordered by lively outdoor cafés. The outdoor markets… Not to mention the gelato!

Tuscany and its Etruscan Heritage

The Etruscans were the first civilization of Tuscany, beginning in the eighth century BC, well before the Romans. The name “Tuscany” is derived from the term “Etruscan.” These were an advanced people, thought to be a melding of Greek immigrants and people indigenous to Italy. They built their well-fortified towns on hilltops, reclaiming previously unfarmable land by constructing water systems for irrigation. By 500 BC, Etruscan culture had spread across Tuscany, controlling much of central Italy, including Rome.

A wealth of Etruscan art and artifacts has survived across the centuries, preserved by being buried with the dead, as with the Egyptians. Etruscan tombs, composed of multiple chambers, are carved into the rock and furnished like a house for the next world, complete with food, jewelry and weapons. The Etruscans crafted exquisite, intricately delicate filigreed jewelry, reflecting a wealthy and sophisticated culture with refined tastes.

Each Etruscan town was its own independent city-state, with an autonomous government. Over the centuries, the towns banded together into three separate leagues, made up of 12 cities each. By the 4th century BC, the Etruscans were steadily losing power to the Romans, who ultimately brought about their demise. As Rome grew in power, it conquered and absorbed the Etruscan city states one by one until they vanished into the larger civilization Rome carved out for itself.

After the fall of the Roman Empire, Tuscany had a succession of rulers until the 12th-century when Tuscan cities gradually began to regain their independence as republics. By the Middle Ages, some of these cities became wealthy through commerce, trade and banking, including Florence, Siena and Pisa. But there was an almost perpetual state of rivalry, war and mayhem between the city states, each jockeying for power over the others. Ultimately Florence ended up in the lead.

Five Places to Visit First in Tuscany

On your visit to Tuscany, you owe it to yourself to enjoy the full experience, balancing small, quaint towns with large, well-known cities. Start in the medium-sized city of Siena. Then hop about among the three small hill towns of San Gimignano, Montepulciana and Cortona. Save Florence for last.

Throughout your time in Tuscany, you will be perched on hilltops in enthralling, ancient towns, surrounded by gorgeous countryside, with vineyards and fields reaching out in every direction, as far as your eye can see. Travel about by train so your journey will be as much of a delight as your arrival. And determine to place as much emphasis on the being there as you do on seeing sights.

Start your wanderings in Siena

First to Siena, Frozen in Time

Start your Tuscan adventure in Siena, Florence’s rival city, now frozen in time. Surrounded by olive groves and the vineyards of Chianti, Siena is one of the most beautiful cities of Tuscany. Set on three hills, the city is connected by winding alleyways and steep steps.

Like other Tuscan hill towns, Siena was first settled by the Etruscans (in 900 BC to 400 BC). Centuries later, in 30 AD, the Romans established a military outpost in Siena. The town developed into a busy little trading post, advanced by the Via Francigena, the trade and Pilgrim road linking Rome to France. This greatly increased Siena’s importance.

Siena grew in economic and military power to become a major and powerful city of 60,000, equal in size and importance to Florence. Like Florence, Siena commissioned great artists to create beautiful monuments and artwork as evidence of its stature.

But Siena’s golden age ended abruptly with the devastating plague that swept through Italy, France, Germany and other European countries, spread by infected fleas carried by black rats. Around 1/3 of the population of Europe died in this plaque. When the plague hit Siena in 1348, it killed its victims almost instantly… the ill would “fall over dead while talking.” There were so many deaths that some believed this to be the “end of the world.”

Fervent friction developed between Siena and Florence as they recovered from the plague, with both cities determined to enlarge their own territories at the other’s loss. Siena won some of the many battles between the two cities. But eventually Florence gained the upper hand in 1555, in alliance with the Spanish crown. Siena surrendered to Spain and the Spanish king ceded Siena to Florence to pay off his huge debts to the Medici family.

In Siena you will have your opening experience with a grand Piazza, Piazza del Campo, standing at the heart of the city. Find the Fountain of Joy and the statue of Venus for up-close looks. This vast open space was once the center of commerce and the scene of executions and bullfights. Now it is home twice a year to the famed Palio–the bare-backed horse race where the 17 neighborhoods (“contrade”) compete fiercely to win the highly-coveted banner. The Palio race lasts only one minute, with three laps around the piazza, and is attended by 60,000 wildly cheering viewers.

Also, you will take in your first excessively resplendent Duomo, with its façade of gold-leaf and pink, white, and green marble. Take time to study closely the 56 masterpieces embedded in the floor panels, depicting stories of legend, fortune, journeying, wisdom and rape. If you are in Siena on a Wednesday, take in the weekly market. And consider signing up for the 2-hour class at the Tuscan Wine School near the Duomo to begin your introduction to Tuscan wines.

On a day trip from Siena, venture by train to little San Gimignano

To San Gimignano, a Town of Towers

San Gimignano is a small walled village, about halfway between Florence and Siena, along what was once the trade and pilgrim route between France and Rome. It is famous for its medieval architecture and defensive towers, rising above the town walls, visible as you ascend the hill towards the town.

These protective towers were built by patrician families at the height of the town’s glory, as symbols of their wealth and power. The towers also served a defensive purpose against attack from external intruders, as well as from rival families within the town walls. Of the 72 towers that once dominated the city, only 14 have survived, continuing to give San Gimignano its feudal atmosphere and appearance. To see a replica of the town as it appeared in the 1300s when all of its towers were still standing, visit the San Gimignano 1300 exhibit, inside the town walls.

Like Siena, San Gimignano was decimated by the plague, which reduced its population from 13,000 to 4,000, and forced the town to submit to Florence. Florence ordered that most of the towers be removed. After Florence moved the trade and pilgrim route to bypass San Gimignano, the town’s fortunes declined, leaving it preserved in its 13th-century form.

San Gimignano is a maze of buildings from times gone by, threaded by narrow pedestrian-only streets, and bordered by intriguing shops and galleries that offer the work of local artists and artisans–leather, handmade jewelry, embroidery, ceramics, paintings. There are a few interesting sights to see here. But, more importantly, this is a town where you can explore at will, enjoy a delicious Tuscan lunch, and look out past the ancient walls and across the countryside while sipping a glass of wine at an outdoor table.

Next move your home-base to Montepulciana

To Montepulciana, Famous for its Vino Nobile

Next stop after Siena is the small hill town of Montepulciano, 43 miles southeast of Siena and 77 miles southeast of Florence. Known to be one of the most beautiful hill towns in Italy, Montepulciano is built along the curve of a 1,985-foot limestone ridge–a favorite place for the nobility of Florence to build their luxurious second homes.

The town is encircled by walls and fortifications, and filled with Renaissance-style palazzi, ancient churches, charming piazzas and hidden corners, as well as vast panoramas looking out over the surrounding hills and valleys. But the town is chiefly known for its excellent local wines, referred to as the “Vino Nobile.”

Piazza Grande is the heart of Montepulciano and the setting for its main events, including the barrel-racing contest, Bravio delle Botti, held in August every year. The sequel to the Twilight Vampire SagaNew Moon was filmed here in 2009.

Montepulciano Market Day is on Thursday, with the marketeers arriving early to set up their draped and shaded stalls. Local crowds follow, pulling haversacks on wheels, to gather up fresh food for the week–vegetables, breads, olives, oils, salamis and cheeses–and to peruse the other goods. Join them!

From Montepulciano, take a day trip to the nearby hill town of Cortona, 20 miles to the northeast…

To Cortona, Under the Tuscan Sun

Little Cortona–featured in the popular film Under the Tuscan Sun–is another charming town perched on top of a hill, enclosed by stone walls that dates back to Etruscan and Roman times. This dominant position above the valley offers a spectacular view from all over town of the surrounding valley and as far as Lake Trasimeno.

This is another town with interesting museums, but even more interesting streets and shops, restaurants and markets. The Etruscan Academy Museum is outstanding, displaying many artifacts from the Etruscan archaeological sites in the area. Excellent red wines are produced here and in the surrounding area, and all the wine bars offer a wide selection. Market day is every Saturday morning.

In Cortona, stop in a leather shop along the main street, Via Nazionale, and select your perfect bag with the friendly help of the owners. Then ask that they point you in the direction of a restaurant with domed Etruscan-style ceilings that offers local Tuscan food and feast on a delicious lunch of mushroom-stuffed ravioli and vino bianco.

Complete the loop of your journey, ending up back to Florence

To Florence, Birthplace of the Renaissance

Arriving in Florence, you immediately will be surrounded by remarkable sculpture and architecture, palaces and piazzas, masterworks of Renaissance art and intricate work by current-day artisans. Here you will experience unsurpassed art and sculpture, masterpiece upon masterpiece. You will shop the leather markets and sit alongside the piazzas, people-watching and sipping delightful Italian wine. You will look up at the glowing marble of San Miniato, perched high above Piazzo Michaelangelo, across the Arno River in the “Oltrarno.” Florence is best known as the birthplace of the Renaissance and the meeting place for artists and architects, scholars and bankers. It is home to many of the most celebrated masterworks of all time.

Julius Caesar founded the city in 59 BC, named it “Florence Shia,” meaning “flourishing,” and designated it as a haven for retired military veterans. The pattern of the city’s design was in the manner of a military camp.

The powerful Medici banking family ruled the city from behind the scenes for three centuries (15th through 17th) and became avid patrons of the arts. Many of the era’s most influential artists flocked to the city to create their masterpieces, including Ghirlandaio, Michelangelo, Botticelli, and Leonardo da Vinci. Their frescoes, sculptures, architecture and paintings bedeck the churches, squares, and palaces throughout the city.