Eight ‘Must See’ Towns in Tuscany

I recently visited Tuscany and recommend eight beautiful, diverse towns worth visiting for their architecture, history, food, surrounding landscape and museums.

When one thinks of Tuscany, images of rolling green and gold fields, tall cypress trees, walled villages, and medieval castles come to mind. As part of a vacation to northern Italy, first spending a week on Lake Como, we then ventured south to explore the scenic countryside and many diverse towns within Tuscany, and savor the flavors of Tuscany.  

We based ourselves in a beautiful, remote hilltop resort named Borgo di Colleoli, about eight miles southeast of Pontedera. The resort is a restored medieval castle that over the years became an aristocratic villa and estate, encompassing several buildings with beautiful interior frescoes and moldings. The resort rooms are located within the original castle and barns, and features two large swimming pools, a restaurant and bar, and numerous trails and terraces to take in the stunning Tuscan vistas. A long gravel alley lined with old trees leads to the resort, and I found myself taking photos of it many times throughout our stay, capturing the light at different times of day. The nearest village, Palaia, is a sleepy hamlet consisting of narrow roads lined with medieval buildings, and a few restaurants.

Using the resort as our base, we set out each day to a different destination in Tuscany. Each day we visited wonderful and unique places throughout Tuscany, and below I describe eight towns that I recommend everyone should visit. At the end of each day, after hours spent on roads and tourist heavy places, I was always happy to return to the beautiful and peaceful locale of the resort.

Florence

No trip to Tuscany is complete without visiting its largest and most important city – Florence. This beautiful city on a plain with its attractive buildings lining, and bridges crossing the wide Arno River, is one of the most visited places in the world. Florence is the capital of the Tuscany region, and is considered by many to have been the birthplace of the Renaissance. During the medieval period, it was one of the wealthiest cities in Europe, and the remnants of this wealth can be found throughout the city, including works of art and architecture.

Before this visit, the last time I had been in Florence was in the early 1990s, and not much had seemed to change – massive crowds of tourists filling the piazzas, heavy traffic of cars and motorcycles meandering through its streets, the beautiful black and white marbled Duomo, narrow pedestrian streets lined with leather stores and great restaurants serving local traditional foods, and the crowds of people walking along the covered Ponte Vecchio.

The Piazza della Signoria is one of the most popular tourist areas in Florence due to its collection of statues including a replica of Michelangelo’s David statue. While many tourists may believe it is authentic, the original statue can be found at the Galleria dell’Accademia. Overlooking the piazza is the impressive stone built Palazzo Vecchio, or town hall, with its large clock tower.

We reserved tickets ahead of time to visit the Duomo (Santa Maria del Fiori) and adjacent Baptistry of St. John. Construction of the massive black-green and white marbled cathedral began in 1296 and was completed in 1436. The gothic interior of cathedral includes 44 stained glass windows, with depictions of saints, Christ and Mary. Part of our tour included climbing over 450 steps to the dome, where we got a close view of the painted ceiling containing a representation of the Last Judgement.

The most recognized landmark in Florence is probably the Ponte Vechhio, or Old Bridge. Built in the 14^th century, the bridge crosses the Arno, and is lined with shops held up by stilts. Strolling past the bridge in either direction along the river affords excellent views for taking photographs of the bridge and overall cityscape.

Another important landmark is the Palazzo Medici, a Renaissance palace built in 1444 for the famous Medici banking family. The palace incorporates Roman style architecture. Within the palace, including the Magi Chapel, are works of art including frescoes of the Medici family, and various biblical scenes.

San Gimignano

The beautiful hill town of San Gimignano, located an hour south of Florence, is recognized as a UNESCO World Heritage Site. It has become a very popular destination in Tuscany, due to its attractive architecture and skyline of many medieval towers. This heavy tourism has resulted in a very polished town packed with people from all over, catered by high end restaurants and souvenir shops. The towers were built by feuding noble families as symbols of wealth. These families had their own private armies, and the towers were built for both protection and ego. Today, 14 of the original 72 towers still remain. Visitors can climb the tallest tower (at 200 feet) known as Torre Grossa, located at the City Hall.

The Piazza del Duomo is where the town’s Romanesque cathedral is located. The 12^th century church includes frescoes by Ghirlandaio within the Santa Fina chapel, that recount stories from the New and Old Testaments.

Volterra

From San Gimignano, we traveled to the nearby hilltop town of Volterra. Volterra was settled in the 8^th century BC, and was one of the twelve main towns that belonged to the Etruscan confederation. The attractive town is surrounded by ancient Etruscan walls entered by six arched gates. Some of the town’s important relics include the relics of an ancient Acropolis and a Roman Theater built in the 1^st century BC. The Cathedral of Santa Maria Assunta (dating to 1120) and the Baptistry of San Giovanni, both examples of medieval architecture, can be found on the Piazza San Giovanni. The Piazza dei Priori is the main civic square, and the Palazzo dei Priori (town hall) sits on the square. The building, with its tall bell tower, is the oldest civic building in Tuscany. One of the appealing aspects of Volterra is that while it has some similar aspects as San Gimignano such as towers, it has much less tourism and thus has a less polished, and more authentic feel to it.

We visited the Torture museum (Museo della Tortura), one of five located throughout Tuscany. The small museum contains over 100 torture instruments used during interrogations dating between the 16^th to 18^th centuries. While observing the macabre exhibits, it made me glad that I was living in a somewhat more enlightened period.

Monteriggioni

We stopped in the tiny walled village of Monteriggioni on our way to Siena. You will only need about an hour or two to visit Monteriggioni. The village, built in 1213, is known for its medieval fortifications and fourteen watchtowers. It was built by Siena to protect the area from neighboring Florence. The entrance to the town is through the Porta Franca gate, just above a parking lot. The Piazza Roma is the main square, surrounded by medieval buildings. Within the town is the 13^th century Church of Santa Maria, and the Monteriggioni in Arme Museum that includes replicas of ancient weapons, and miniature displays of battles, military history and castle life. You will need to pay to walk along the castle walls, which offer views of the beautiful Chianti countryside.

Siena

One of the most important cities in medieval Europe, Siena was a major banking center until the 14^th century. Today, Siena is known for its cuisine, medieval architecture, museums, and the Palio, a famous horse race that occurs on Piazza del Campo.

On Piazza Tolomei, is the Palazzo Tolomei, one of the oldest palaces in the city, built in 1275 by the Tolomei family. It was the first permanent headquarters of the Sienese commune, and stands across from the Romanesque style Church of San Cristoforo.

The highlight of Siena is the majestic Siena Cathedral (Duomo). Construction of the cathedral began in the 12^th century and was largely completed in 1380. However, some of the interior elements were not completed until the 1800’s. Partial walls of a proposed, but never completed expansion are also evident. The exterior of the cathedral is decorated in white, greenish-black, and red colored marble. The interior walls are decorated in alternating white and black marble, and the floors are laid in various mosaics that tell stories, such as the Massacre of the Innocents by Matteo di Giovanni in 1481. One of the most beautiful sections of the cathedral is the Piccolomini Library. The ornate library is covered in beautiful frescos of scenes representing various stages in the life of Pope Pius II. Within the library is a collection of manuscripts collected by Pope Pius II’s nephew, who later became Pope Pius III.

We spent time on the Piazza del Campo, which seems to be the center of activity in Siena. The shell shaped piazza is built on a slope, and is surrounded by medieval buildings. Outdoor cafes on the upper part of the piazza provide good spots to people watch and take in life in Siena. Adjacent the piazza is Pubblico Palace, a gothic style town hall and tower.

A good place to capture a skyline view of the medieval part of city is from Piazza San Domenico, located to the west near the Artemio Franchi Stadium.

Pienza

The small walled hilltop town of Pienza is located about an hour by car southeast of Siena. Pope Pius II was born in Pienza, and later he led the redesign of the town to embody humanism and architectural harmony. Piazza Pio II is the main square in the town, and the square is surrounded by the Duomo, and the Piccolomini Palace, the summer residence of Pope Pius II. Pienza is known for its production of pecorino cheese, which is on the menus of local restaurants and sold at local shops.

If you ever saw the movie Gladiator, you will recognize the surrounding wheat fields and a trail dotted with cypress trees that was used in the last scene. The film location can be accessed by a road at the west end of the old part of the town (Piazza Dante Alighieri) that leads to a trail. The walk from town is all downhill and takes approximately twenty minutes. Follow signs for ‘Pieve di Corsignano.’ While you may build up a sweat walking back up, the stunning view makes the hike well worth it.

Montepulciano

The hilltop medieval town of Montepulciano, just east of Pienza, sits 2,000 feet high on a limestone ridge overlooking the Orcia Valley and its rolling fields filled with vineyards. This area of Italy is known for its production of red wine, including the Nobile di Montepulciano.

The spot was originally settled by Etruscans in the 4^th century B.C. Today, the linear shaped town is accessed by two gates (Porto al Prata to the north and Porto delle Farine to the south) that open to narrow streets lined with shops and restaurants that climb toward the historic center. An interesting and whimsical site a few blocks south of the Porto al Prata is the Torre di Pulcinella, a clock tower topped by a figure of the Pulcinella, a commedia dell’arte character.

Piazza Grande, is the heart of the town, where the barrel racing Bravio delle Botti contest is held each August. Also on the piazza is the 14th-century Palazzo Comunale, with a tower offering amazing views of the surrounding valley.

At the south end of the town, we briefly visited the Fortezza Medicea. The interior of this old castle has a wine bar with a glass floor exposing archeological findings. An adjacent terrace provides views to San Biagio church and the Ocia Valley.

Lucca

We stopped in the city of Lucca on our way back to Milan before flying back to the U.S. Unlike some of the hilltop towns we visited, Lucca sits on a plain adjacent the Serchio River, surrounded by verdant hills. Lucca is known for its well preserved Renaissance walls that encircle the historic part of the city. Along the tops of the walls are wide tree lined pathways popular with both pedestrians and cyclists. Outside the walls is a wide greenbelt that provides open space separating the historic city from the surrounding urbanized area. Within the walls, the city is laid out in an orderly rectangular grid of narrow cobbled streets and interspersed square piazzas. The one exception is the Piazza dell’Anfiteatro, an elliptical shaped piazza that was the site of an ancient Roman amphitheater that once held seats for 10,000 spectators. The piazza is entered through four covered gateways. Within the piazza is public art, and outdoor cafes. We sat at one café and struck up a conversation with two women visiting from England.

I enjoyed Lucca because while there were certainly tourists, it wasn’t overrun with them as in other places we visited. The city felt very authentic, with a mixture of locals, students, workers and tourists. In fact, Lucca would be a place that I would enjoy spending more time, perhaps even living part time.