Cities with historic walls to visit in Tuscany

Tuscany for centuries was divided into independent kingdoms ready to attack and defend themselves if attacked. As a reminder of those times of division and strife there remain numerous walled cities that allow us to touch upon the history of the territory.

Which Tuscan cities with historic walls are worth visiting? Here are the ones not to be missed!

LUCCA

Lucca is the walled city par excellence as well as the only one not to have been conquered by the Medici also thanks to its city walls. The history of Lucca’s walls begins with the founding of the city and continues until the early 17th century with progressive extensions and consolidations. The one that currently exists, erected between the 16th and 17th centuries, is the fourth city wall with which Lucca has been equipped over the centuries. And it represents the greatest example in Europe of walls built according to the principles of modern-style fortification that have been preserved to this day. With the loss of their defensive function, they were converted to civilian use in the early decades of the 19th century. Today they form a large urban park, where citizens and tourists go for walks, cycling and jogging. Walking on the walls, among ancient trees such as plane trees, horse chestnuts and oaks, one can also see unseen glimpses of the city’s main monuments.

MONTERIGGIONI

Situated on a gentle hillside overlooking the surrounding countryside, Monteriggioni is a unique place that seems to have stopped in the Middle Ages, with its perfectly intact walls around the town. Dante Alighieri was so impressed by it that he compared his vision to that of the giants placed in Inferno: “[…] however, that, as on the round circle Monteriggion of towers crowns itself, so the proda that ‘l pozzo surrounds torregiavan di mezza la persona li orribili giganti, cui minaccia Giove del cielo ancora quando thona.” Built in the 13th century, half-destroyed in the 17th century and rebuilt two centuries later, the city walls are interspersed with 14 watchtowers and two gates (Porta Franca or Romea and Porta di Ponente). Walkways on the walls allow you to see the village from above, offering a different perspective of the town. Take your time to also admire the magnificent view offered by the surrounding hills.

VOLTERRA

Volterra is one of the few Tuscan cities to have preserved both city walls that have protected it throughout its history. However, both the Etruscan one (built around the 4th century B.C.) and the medieval one (dating back to the 13th century) have undergone major remodeling and restoration over the years. The city gates, which open into the city walls, are: Porta all’Arco, which constitutes the main architectural monument of Etruscan Volterra; Porta Pisana (now commonly called di San Francesco), the only one that still preserves traces of the frescoes that were once present in all the gates; Porta a Selci, near the Medici Fortress; Porta Marcoli, which put the city in direct communication with the Olivetan monastery of Sant’Andrea; Porta Fiorentina, formerly called di Sant’Agnolo; and those of Docciola and San Felice, where there are important hydraulic springs.

MONTEPULCIANO

Perched on a hilltop between the Val d’Orcia and the Val di Chiana, Montepulciano is a charming medieval town. The walls that enclose the town refer to an urban city expansion of the first half of the 13th century, although much of the town wall has undergone several reconstructions over time. In May 2024, the Poliziano Path was opened along the walls, a walkway that connects Porta delle Farine with the area of Piazza Santa Maria dei Servi, passing near the birthplace of the great humanist Agnolo Ambrogini, known as the Poliziano. The path, which is more or less 200 meters long, provides an impressive view of the Val di Chiana Senese and Aretina valleys, toward Cortona and the lakes of Chiusi, Montepulciano and Trasimeno, all the way to the chain of the Apennines.

FIESOLE

Fiesole is the town that stands on the hill immediately behind Florence. Its walls, dating as far back as the 4th century B.C., bear witness to its Etruscan origin. Referred to as “cyclopean,” they were built with huge square blocks of pietra serena, laid dry and using a pseudoisodomic technique. Over time they have defended the city from numerous sieges, the last of which was that of the Republic of Florence, which conquered Fiesole in 1125 after years of wearisome battles and reprisals. The section on the northern side (on Via delle Mura Etrusche) is particularly well preserved, while on the southern side, facing Florence, only a few traces remain, incorporated into some buildings. By contrast, almost nothing remains of the gates that gave access to the city.

SIENA

Dating mainly from the Middle Ages, the walls of Siena are probably not one of the city’s best-known monuments, but they are undoubtedly worth a visit. They extend for about 7 kilometers and their development has remained intact almost in its entirety (demolitions carried out in modern times have affected only short sections). The walls we see today are the result of a long process of modification and augmentation that began well before the early Middle Ages and ended in the 16th century. They had a defensive and military function for centuries, from the construction of the first nucleus to the fall of the Sienese Republic, while from the end of the 16th century, when Siena came under Medici rule, they took on administrative functions, mainly customs duties. Seven gates still in use today open in the wall circuit: Porta Camollia, Porta Ovile, Porta Pispini, Porta Romana, Porta Tufi, Porta Laterina and Porta Fontebranda.

GROSSETO

Grosseto is another city with historic walls not to be missed. The wall was built starting in the 12th century but was destroyed and rebuilt several times over time. Much of its current appearance is due to upgrades carried out in the second half of the 16th century by architect Baldassarre Lanci at the behest of the Medici family. It stretches for about 3 kilometers and has the shape of an irregular hexagon with six corner bastions, one at each corner of the hexagon, in the shape of an arrow (Bastione Cavallerizza, Bastione Maiano, Bastione Fortezza, Bastione Rimembranza, Bastione Garibaldi and Bastione Mulino a Vento). The path on the walls is fully passable and, in addition to offering a picturesque view of the city, makes for a beautiful walk.