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Tuscany: 5 fascinating towns you must visit

Tuscany is rich in beautiful landscapes, delicious cuisine, wines, and a plethora of excellent places to stay — from villas and historic estates to farms, wineries, and other spots perfect for agritourism enthusiasts. Additionally, there are many places here that are of great architectural and historical interest.
15 april 2024
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San Gimignano

One of the most visited towns in Tuscany — those who struggle with crowds may want to avoid visiting during the high season.

You can book a hotel with a discount of up to 65% on the website.

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Photo author - italiatut

There’s plenty to see:

  • The Four Towers — “medieval skyscrapers”;
  • The Palazzo Nuovo del Podestà and Palazzo del Popolo. The latter now houses an art gallery featuring works by Florentine masters;
  • The Cathedral (built in 1148);
  • The Church of Sant'Agostino, where unique frescoes from 1298 have been preserved.

On the last weekend of July, the town hosts the Dentro e Fuori le Mura arts festival, which includes concerts, film screenings, and theater performances. Most of the events are held at the fortress.

How to get there from Florence: by car (1 hour) or by train to Certaldo, then by bus (1.5 hours).

Volterra

A medieval town located 29 kilometers from San Gimignano. The central square, Piazza dei Priori, is adorned by the Gothic Palazzo dei Priori, the oldest town hall in Tuscany.

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Photo author - latuaitalia

The Porta all′Arco gate, built by the Etruscans in the 4th century BC, has been preserved. From here, you can stroll along Via Porta all'Arco to the Roman amphitheater from the 1st century BC (€7 for adults, €3 for children aged 6-12). Another interesting sight is the Medici Fortress, built in 1474 shortly after Volterra was conquered by Florence.

Volterra is mentioned in the novel “New Moon” from the famous Twilight saga by Stephenie Meyer. However, the movie was filmed in Montepulciano, so you won’t find any familiar buildings or squares. But the town offers stunning views of the surrounding fields and hills, especially at sunset. Visit the observation deck in the evening for an unforgettable experience!

How to get there from Florence: by car (1.5 hours) or by train with one transfer (3 hours).

Lucca

An important military camp during the Roman Empire, a city of towers and churches, and the birthplace of Puccini and Paganini.

Lucca
Photo author - Pat Evans

The city is surrounded by a fortress wall, and of the 11 bastions built in the 16th century, 2 have been preserved to this day. All the interesting attractions are concentrated within the walls; the historic center is compact, with typical colorful houses of the region.

Many old churches have been preserved and remain active to this day. Other attractions include the Clock Tower and Villa Bottini with its luxurious park.

You can book a hotel with a discount of up to 65% on the website.

How to get there from Florence: by car (1 hour) or by train (1.5-2 hours).

Arezzo

One of the main Etruscan city-states, built even before Alexandria in Egypt. The city is famous for its residents: Italian poet Petrarch and painter Giorgio Vasari were born here. Arezzo also had its moment in cinema — Roberto Benigni filmed his movie “Life is Beautiful” here, which won the Palme d'Or and three Oscars.

Arezzo
Photo author - Luca Carnesciali

The attractions of Arezzo are concentrated in the medieval center. Be sure to visit the Cathedral (13th-15th centuries), which boasts well-preserved frescoes, the Palazzo delle Logge Vasariane (16th century) designed by Vasari, and the ancient Roman amphitheater and museum.

The locals cherish traditions — every year on the third Sunday of June and the first Sunday of September, the Joust of the Saracens (Giostra del Saracino) is held here. Participants dress in colorful costumes, and horsemen representing the city’s districts compete in hitting wooden targets.

When visiting Arezzo, it's also worth stopping by nearby Cortona. Founded over 2,000 years ago (some say it’s older than Rome!), the town is located on Mount Giostra del Saracino, on the border of Tuscany and Umbria. The events of the Hollywood film “Under the Tuscan Sun” take place here, and after its release, the number of people wanting to live in Cortona sharply increased.

Behind the Etruscan-built fortress wall lies a labyrinth of narrow streets, ancient churches, and cozy houses — this idyllic landscape is unspoiled by modern buildings. It’s no wonder the town is called an open-air museum!

How to get there from Florence: by car (1-1.5 hours) or by train (about an hour).

Siena

A medieval city with many buildings preserved in their original form, having survived bombings during World War II.

You can book a hotel with a discount of up to 65% on the website.

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Siena Cathedral
Photo author - Jimmy Pierce

The central square, Piazza del Campo, has a unique shell-like shape, and all buildings are designed to complement its contour. The key building is the Palazzo Comunale (14th century), which now houses the town hall, the Civic Museum, and a theater. Adjacent to it is the Torre del Mangia, one of the tallest medieval towers, with an observation deck at a height of 88 meters. To enjoy a view of the city from above, you’ll have to climb 400 steps.

Siena has a wealth of diverse museums, some of which offer combined tickets that can save you a bit of money. Here are the most interesting ones:

  • The Civic Museum (Il Campo 1). Visiting it, you’ll see the rooms of the old Town Hall, including the Hall of the Globe and the Hall of Nine, where the members of the government of the Republic of Siena used to meet. Pay attention to the frescoes decorating the walls — they depict how to govern a city to lead it to prosperity.
  • The National Pinacotheca (Via S. Pietro 29). The gallery started with a collection of paintings belonging to Abbot Giuseppe Ciaccheri, and religious-themed works predominate.

How to get there from Florence: by car (1-1.5 hours) or by train (about 1.5 hours).

Using our website, tripmydream, you can find airline tickets starting from 15 EUR. Look for the cheapest flights in the Flight Discounts section. To do this, select the departure point, and the service will find the most advantageous offers for you.

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