Towns of Tuscany

The most beautiful Medieval Towns of Tuscany

We take you through the towns of Tuscany with their medieval city centers. You will immerse yourself in a time when fairy tales were still being told by the fire in the evenings. When handicrafts were still the most important source of income, masterpieces of craftsmanship were created thanks to the creativity of the people. Many of these typical art forms and their works have been preserved in the medieval towns of Tuscany.
The beauty and the rolling hills of the Tuscan landscape have made people settle down in central Italy since ancient times. Small towns emerged in ancient times, which grew rich in the Middle Ages and whose beautiful structure has been preserved for many centuries. This is why the medieval towns of Tuscany with their narrow streets and craft traditions are still so attractive to us today.
Not only the capital of Tuscany, Florence, is rich in works of art. The medieval towns of Siena and Pisa are known for their unique structures and attract millions of visitors to Tuscany every year. We will also show you the lesser-known places, which are sometimes all the more attractive and definitely worth a visit.

We recommend an itinerary in Tuscany for a driving tour with many stops in the smaller villages and finally a few days of bathing on the beautiful sandy beaches.

The Medieval Towns of Tuscany


Siena is located in the heart of Tuscany, the city is known for horse racing. Every August, the individual districts, which are called Contrade, fight for the “Palio” in Piazza del Campo. Anyone who has seen James Bond, Quantum of solace, already knows the place with the horse races. But even without horse racing, it’s worth a visit to the pretty town with the brick buildings. In the centre is the white tower Torre del Mangia. Those who have climbed the 503 steps will be rewarded with a fantastic panoramic view over Siena and the surrounding hills of Chianti.


Lucca is one of the most beautiful places in Tuscany. The square in the heart of Lucca, Piazza dell ‘Anfiteatro. It was built on the ruins of a Roman amphitheater. If you like to climb to enjoy a great view, you should climb the 230 steps on Torre Giunigi. Above grows a tree that provides some shade in the midday sun. Every year in July and August, a very special event takes place in Lucca: the Puccini Festival. The opera festival is dedicated to the composer Giacomo Puccini with his wonderful melodies. The Puccini Festival takes place in an open-air theater on the banks of Lake Maasaiuccoli. In the middle of the green landscape by the lake, the theater offers space for 3400 spectators. Next to it is the Puccini Museum, which houses the graves of Puccini and his wife and mementos from his life.


Who doesn’t know it, the leaning tower of Pisa? It was originally supposed to make the bells of the cathedral sound, but already when the tower was built, it tilted worryingly. Over 200 years they worked on the tower with the success that it was not only skewed, but also crooked, but world famous. The Leaning Tower of Pisa is located in the Square of Miracles, Piazza dei Miracoli, where it stands together with the cathedral and the baptistery and is admired and photographed by millions of tourists.

San Gimignano

San Gimignano is located on a small hill and looks out over the landscape from a height of 334 m.  The beautiful medieval village from the 12th century The 14 towers were listed as a UNESCO World Heritage Site.
The city prides itself on its nobel family towers. Every noble family who could afford it erected their tower status symbol, the higher the more significant. In the centre of San Gimignano is Piazza della Cisterna with its medieval fountain.
The world-famous opera singer Andrea Bocelli invites to a concert in the Teatro del Silenzio in his birth town Lajatico every summer. There is hardly a better reason to plan a trip to Tuscany than to experience a concert by one of the greatest opera singers in this wonderful landscape with an infinite view into a magical seeming one.


From Volterra comes the alabaster. The marble-like stone has been mined here for thousands of years and processed into works of art. One enters Volterra through one of the six medieval city gates. Even remnants of the Etruscan city wall and the Roman theatre are still present. Most of the buildings date back to the Middle Ages and the Renaissance, modern facilities are only visible when inside.


Fiesole is located above Florence and has beautiful views of the Renaissance city with the impressive Brunelleschi dome on the cathedral. Beautiful hotels and restaurants with views are the perfect place for a romantic dinner.


Livorno is mainly a port city. Ferries depart for Sardinia and Corsica. Livorno, with its maritime flair, has beautiful beaches and a remarkable old town around the harbour and Piazza Grande.


Viareggio is located on the Versiliak coast and has wide sandy beaches for a beach holiday with and without children. As early as the beginning of the 19th century, Viareggio, with its beautiful Art Nouveau buildings, was a popular seaside resort for afluents and artists.

Pitigliano and Sorano

In southern Tuscany, the picturesque villages of Pitigliano and Sorano are located in the Maremma, already close to the border with neighboring Lazio. Pitigliano is one of the most beautiful places in Italy, one of the “Borghi più belli d ‘Italia.” The place is famous for its cave dwellings and the Jewish settlement, which can be visited in the caves.

Porto Santo Stefano

The two towns of Porto Santo Stefano and Porto Ercole are located on the peninsula of Monte Argentario in southern Tuscany. Porto Santo Stefano is the main town and departure point to the island of Giglio. The Monte Argentario peninsula is reached through the Orbetello lagoon.

The beautiful medieval old town of Porto Santo Stefano has a castel above the marina and fishing port.

Itinerary in Tuscany

Stations for an Itinerary in Tuscany

Individual Itinerary in Tuscany for self-drivers

Whether you’re renting a car or driving your own car, below we’ve put together a travel program for a week that will take you through the most beautiful cities in Tuscany.

For visitors who have more time and want to get to know more from Tuscany, the program can be expanded at will.

Tuscany in seven days

Day 1 Florence:

You arrive in Florence and experience the romantic city on the Arno during an evening stroll and enjoy the evening at the famous Ponte Vecchio bridge.

Day 2: Florence and the Uffizi Gallery

Take a stroll through the city and discover the most beautiful sights of the Renaissance city with the famous buildings Palazzo Vecchio, the statue of David by Michelangelo Buonarroti and the art collection of the Uffizi Gallery.

The cathedral square in front of the cathedral with the Brunelleschi dome, the bell tower of Giotto and the baptistery are particularly beautiful.

Day 3: San Gimignano and Siena

Today, the tour in the Chianti region takes you to San Gimignano, where you can relax and strengthen yourself after strolling through the medieval village.

In the afternoon you will continue to Siena, where you will enjoy the flair of Piazza del Campo in the evening and end the day with a glass of Chianti.

Day 4: Volterra and the Etruscan Coast

In Volterra, alabaster is mined and also processed into works of art. In the middle of the old town are the workshops of alabaster processing. In the afternoon we continue to the seaside and drive along the “Costiera degli Etruschi,” the Etruscan Riviera, a popular holiday area on to Pisa.

Day 5: Pisa and Lucca

The tour goes to Pisa today and you will visit Piazza dei Miracoli, the Square of Miracles with the Leaning Tower. It’s best to eat on the go in a village inn before heading on to Lucca.

One experience is climbing the Torre Guinigi tower in Lucca.

Day 6: Viareggio and the Versilia Coast

You can spend a little time in Lucca before heading along the Versilia Riviera via Viareggio to Carrara.

Day 7: Carrara

Today is dedicated to marble of the mountains above Carrara. Here it is cut out in huge blocks. You can visit the quarries, there are also guided tours.

Day 8: La Spezia and the Cinque Terre

If you have some time left, we recommend a visit to the Cinque Terre and Portovenere afterward. Find out more of the five villages of Cinque Terre

Peace of Mind

If you book a trip with us, then we take care of all that-including. Hotel, accompanying program, and private guided tours.

Tourist traps


Tipping is expected in the restaurants frequented by foreign tourists. The waiters in these restaurants know very well what is common in your culture. You should know, though, that an Italian usually only pays what is printed on the bill. Importantly, they are considering whether the amount is justified. You can also ask for a proper invoice, which you can also get if you suggest that you need it for business. Speak calmly in your language and use your hands to make it clear what it is all about. If you stay friendly, then it all works out too. By the way, you are legally obliged to take the receipt with you. You may be checked by finance police outside the door.

Italians pay in the restaurant at the checkout when they go out. Money is dirty and shouldn’t actually change hands at the table. Of course, the waiters also adapt to the visitors and you can also have it the way you’re used to from home. But it is better you go to the cashier near the entrance. Especially if you pay by card, want a special receipt and maybe another grappa.

Prices in restaurants and bars

Eating in a restaurant and street café, located in a beautiful piazza and equipped with cosy basket chairs and padded seat cushions, is highly likely to cost more than in a trattoria with neon lighting in an inconspicuous place.

If you only want to drink an espresso or cappuccino, you pay about €1.00 to €1.40 at the counter standing. This takes less than 5 minutes. Table service will usually cost a bit more. It depends where you are.


Be careful with handbags or backpacks that are easy to open. Pickpockets, sometimes even by children, are traveling in populated public places and especially in markets. They appear in groups and skillfully pull wallets, mobile phones etc. out of your pocket or bag and pass it on to an accomplice. Carry all bags well sealed on the body.

Hotels and Holiday Houses


We have a few selected hotel partners where we almost always get good rooms. It’s not always easy, but we’re mostly able to do that.

Overnight rates in Italy are difficult to plan for. Depending on the exact date of travel and the local booking situation, the hotel price may vary greatly. As soon as we get your request and we know what matters to you, we will take care of it and make an individual proposal for you. To do this, we need to know whether location, comfort, price or charm matter most to you. We are happy to take care of your wishes. A hotel with charm or something economical for smaller budgets. We know the area well and will certainly find something that will inspire you. Please provide special requests at your request.

Holiday Houses

In Tuscany, there is a huge selection of beautiful holiday apartments and holiday homes and villas by the sea of all sizes and for all budgets.

Map of Tuscany

You can hover over the dots on the map to see the name of the city. A click will bring you to the page of that city.

Map of Tuscany
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