6 Charming Towns Across Tuscany

cozy street in Lucca Italy
Cozy Street in Lucca, Italy

Scattered throughout Tuscany’s diverse natural landscape, well-preserved ancient hilltop towns and walled cities flourish. A visit to any of these charming destinations is sure to be filled with Renaissance art, local food, and Italian culture. 

Arezzo

arezzo italy beautiful street

About an hour from Tuscany’s capital city, Florence, is the quieter, yet equally culturally rich city of Arezzo. The beautiful city with a population of just under 100,000 offers breathtaking Medieval and Renaissance architecture. The famous Medici family controlled the area for a period of time, so art and culture is at the forefront of Arezzo’s history. 

Museums and churches all across Arezzo feature amazing artworks from renowned Renaissance artists. At the Church of San Francesco, visitors can book a time slot to get an up close look at frescos by famous artists like Piero della Francesca. On the outskirts of the city, you can find the remains of a Roman Amphitheatere. This structure, which dates back to the 1st century, still hosts shows and events in the summer months. 

Arezzo’s location right on the edge of the Chianti region makes it a prime spot to sample some of the area’s world renowned wine varieties. Test out a few bottles at one of the wine bars in town, or at a trattoria where you can also sample the region’s hearty meat dishes.

Lucca

lucca italy scenic view beautiful tuscany

A visit to the walled city of Lucca, just an hour west of Florence, transports you back in time. Aside from the occasional police officer on patrol, the city does not allow for cars so it is extremely pedestrian friendly. Walking around the town allows you to take in all the beauty of the historic cobble stones streets. Or, a popular option is to rent bicycles for the day and travel from piazza to piazza. 

Lucca is lovingly known as the city of 100 churches because of its expansive amount of religious buildings scattered within the walls. While it would be nearly impossible to visit all of these inviting chapels and churches, a trip to Lucca would be incomplete without stepping foot into some of the religious sites. 

In Piazza San Michele, visitors can shop at some of the town’s shops, grab a gelato or take a seat at a café. No matter how you spend your time there, you will be able to see the famous Church of San Michele which dates back to the 8th century. 

During your time in Lucca, be sure to taste some of the province’s famous veal dishes or soup of farro. Whatever you order will surely be prepared with some of Italy’s finest extra virgin olive oil which is found throughout Tuscany.

Pisa

pisa italy leaning tour beautiful towns tuscany

Pisa is a world-famous city in Tuscany most well-known for the iconic Leaning Tower of Pisa. Pisa is located about one hour and twenty-five minutes from Florence. It is also an easy drive from Siena, Lucca, and the Ligurian Sea.

The Leaning Tower of Pisa has been leaning since the start. The foundations of the Tower were laid in 1173. However, to regional conflicts and politics, it was not completed until 1372. The Leaning Tower of Pisa has been leaning ever since due to the soft ground underneath.

There is so much more to see and do in Pisa besides the Tower! Visit the Baptistery of St. John, located right next to the Leaning Tower of Pisa. Located right next to the Leaning Tower of Pisa, the Baptistery of St. John is just slightly taller than the Tower. This 12th century ornamental baptistery dedicated to Florence’s patron saint features stacked domes and octagonal plan, making it one of the most fascinating pieces of religious architecture in this beautiful Tuscan town.

Another notable attraction in Pisa is Piazza dei Cavalieri (Knights’ Square). This was once the center of medieval Pisa and presumably the site of the Roman Forum. Visitors will see the Palazzo dei Cavalieri (Palace of the Convoy), which was once the headquarters for the Knights of St. Stephen.

Foods to try while in Pisa include truffles, and the Pisan Tripe.

San Gimignano

italy beautiful towns of tuscany San Gimignano

San Gimignano is a walled hilltop town located about 55 minutes south of Florence, and 30 minutes north-west of Siena. This charming medieval town boasts many narrow, winding lane and gnarled stone buildings.

The town’s most famous feature are its towers, which earned this small town the nickname “San Gimignano delle belle torri”. Only thirteen towers remain today; there was once a total of over 70 from a total of over 70 at the towns peak of wealth and influence in the 1300s.

Spend your afternoons walking about the twin central squares: Piazza della Cisterna and Piazza del Duomo, located in the heart of San Gimignano. Another notable spot to visit is Pieve di Santa Maria, a beautiful stone parish church, just five minutes from the city center. You can tour the monastery and admire the surrounding natural wonders of Tuscany.

For a local wine tasting, take part in the Wine Experience La Rocca. The wine to try in San Gimignano is Tuscany’s only dry white DOCG wine, Vernaccia di San Gimignano. You may book either an easy wine tasting or even a top masterclass, a two-hour lesson that dives into the world of wine in Tuscany. 

During your visit to San Gimignano, a must visit is to their famous Gelateria Dondoli, located in the central Piazza della Cisterna. There is usually a long due, but it is well worth the wait! Flavors to try include Pistacchio Sicilia, Tiramisu, Cioccolato Bianco, and Lavender.

Siena

medieval city of siena italy beautiful town

The medieval town of Siena is about one hour south of Florence. In the heart of Siena is Piazza del Campo, a stunningly picturesque round-shaped piazza that is in walking distance to many notable attractions. In fact, the city center is closed to traffic, so it makes for the perfect destination to spend your day leisurely exploring on foot. 

Located in the heart of Tuscany, Siena can be easily reached from the other cities in the region by car, train or bus. Siena Train Station is located outside the city, but it is well connected with the city center by buses.

One of the most famous sites to visit in Siena is Piazza del Campo that stands in the center of the town square. In the square, visitors can admire the Fonte Gaia, the largest fountain in Siena that was originally decorated with sculptures by Jacopo della Quercia.

For those who appreciate Italian fine art, discover a full collection of national works inside the Pinacoteca Nazionale. The art collection at the museum features many notable late medieval and Renaissance pieces that evoke the rich history of Siena.

If you are looking to get as many steps in as possible, challenge yourself with a climb up the city tower, Torre Del Mangia. There are over 400 steps to climb but the 360-degree views at the top will be well worth the effort. 

For an overnight stay, look to Hotel Le Fontanelle perched on a hilltop in Castelnuovo Beradenga that features upscale dining, an indoor and outdoor pool, and sprawling outdoor Tuscan gardens.

Vinci

veduta vinci italy
Veduta in Vinci. Courtesy of Vinci Tourism

Vinci is an historic hilltop town, located about 50 minutes west of Florence in the region of Tuscany. This beautiful small town in Italy is most famous for being the birthplace of the world renowned Renaissance artist and inventor, Leonardo da Vinci. 

The train is one of the most convenient methods of transportation for traveling to Vinci. Visitors should take train to Empoli (if you are traveling from Florence or Pisa). Then, catch a bus to Vinci from Empoli Train Station.

During your visit to Vinci, visit the small farmhouse called La Casa Natale di Leonardo. This was where Leonardo da Vinci was born on April 15th, 1452.

There are also several important museums related to da Vinci in the town’s small historic center. There is the Leonardo Library and the Municipal Museum Leonardo, and the Castle of the Counts Guidi. The castle is a spectacular medieval fortress that dates back to the eleventh century.

Dine at Borgo Allegro in Vinci, an award-winning restaurant known for their extensive collection of wines including local and regional wines, as well as a relaxed and welcoming atmosphere. For overnight accommodations, Hotel Monna Lisa is within an easy walking distance of Vinci’s museums, restaurants and attractions. Nearby outdoor activities include hiking, golf, and horseback riding.

Another accommodation is Villa Dianella. Villa Dianella is a luxurious, family-run resort set in a 16th-century hunting lodge just under five miles outside of Vinci. Guests may take Tuscan cooking classes or indulge in an olive oil and wine tasting.