Experience the blend of old and new in some of our favorite Tuscan towns.

In many parts of Italy, elements of the country’s long history have been remodeled and renovated over the centuries as people’s needs evolved. In Tuscany, the region’s especially fractious political climate led to many of its cities building incredible fortifications in the Middle Ages and Renaissance. Throughout the region, you’ll find towns with a fortified wall built around the perimeter of the city and a tall tower that, in many cases, served as a watchtower to spot enemies. In some places, these structures were a means of flaunting wealth and power. Today, all these sturdy stone walls and tall towers are a romantic counterpoint to the rolling hills and vineyards, and they attract tourists from all over the world.

While there are so many incredible places to experience history in a new way throughout Tuscany, here are some of our favorites: 

Lucca

Then: Northeast of Florence, Lucca’s defensive walls have been around since ancient Roman times. They were rebuilt in 1504 to help defend the city against the expansion of Florence and the ruling Medici family. It’s these walls that helped Lucca stay one of the few cities in Tuscany that did not fall to the Medicis and remained independent.

Now: Lucca’s perimeter walls have today been revamped into a lovely walking path. You’ll see walkers, runners, and bikers alike enjoying this open, airy 3-mile loop, which provides beautiful views of the city and the surrounding countryside. If you’re traveling to Lucca, bring your walking shoes and enjoy!

Pisa

Then: The prosperous stronghold of Pisa built La Torre Pendente, or The Leaning Tower of Pisa to celebrate the overall wealth of the city. Construction on this belltower of the city’s cathedral began in 1173 but was not finished until 1350. This lengthy delay led to its famous tilt, as the foundation of the tower had already settled unevenly in the ground when the rest was built. 

Now: Today, Pisa’s leaning tower is one of the most famous structures in the world. Although access is limited for safety, you can climb to the top to glimpse a view of Pisa’s gorgeous duomo. Don’t want to wait in line? Join the millions of tourists taking the iconic picture standing in front of the tower with hands raised as though you are keeping the tower aloft.

San Gimignano

Then: While some medieval towers in Tuscany were created to protect the city from invaders, others, like those in San Gimignano, were a way to display wealth and power. In fact, San Gimignano once had 72 different towers, giving it the nickname “The Manhattan of the Middle Ages.” Each medieval skyscraper was owned by a different wealthy family as they vied for the tallest and most impressive display.

Now: Although only 14 towers stand today, San Gimignano’s skyline is still a sight to behold as you drive into town. Now a UNESCO World Heritage Centre, San Gimignano is a small snapshot in time of Italian feudal society. Climb the tallest of the remaining towers, Torre Grossa, to transport yourself back in time and experience a full view of the historic town below.

Siena

Then: Only an hour from Florence, Siena was one of the Tuscan capital’s major rivals in the 12th–14th centuries. Turmoil between the two cities can be seen in the defensive structures built around the city, like the fortified walls, maze-like streets designed to confuse intruders, and the central tower. Built in 1338–1348, Torre del Mangia was the tallest tower in Tuscany at the time. Constructed to be the same height as Siena’s cathedral, signifying the equal power of church and state, Torre del Mangia became a stronghold for governors and an essential watchtower as tensions with Florence rose.

Now: Today, Siena is one of the best-preserved medieval towns of its size in Italy. To see it all, climb the stairs to the top of the tower from the entrance off Siena’s main square, Piazza del Campo. While the climb can be challenging, the gorgeous view of Siena’s rust-colored rooftops is unforgettable.

Volterra 

Then: On a hilltop in Tuscany lies Volterra, a town that dates back to the 8th century BCE. It was founded by the Etruscans, an ancient people that inspired many later customs of the Romans. The original walls of Volterra are an engineering feat of this early age that date all the way back to the 4th century BCE, when they were built to protect the Etruscans from attack—particularly from its southern neighbors, the newly growing Rome.

Now: A treat for the history-inclined, modern Volterra is still full of archaeological and ancient ruins, including parts of its original ancient wall. You can walk along the original wall at Porta dell’Arco, one of Volterra’s six gates. Here, you’ll be treated with a breathtaking view of Tuscany’s vineyards below, a perfect spot to enjoy the beauty and history of Tuscany all at once and appreciate its blending of past, present, and future.