A Road Trip through Tuscany – The 7 Most Special Cities & Towns

1. The capital of Tuscany; Florence

Florence – the beautiful capital of Tuscany – is one of our favorite cities. The city is known for its impressive architecture, such as the cathedral the Duomo, the iconic bridge the Ponte Vecchio and the influences of famous artists including: Michelangelo, Botticelli and Donatello. It is therefore one of the art cities of the world.

But Florence has much more to offer, such as delicious Italian cuisine, royal palaces and gardens, spectacular viewpoints, sculptures and atmospheric squares. Are you planning a trip to Florence soon? Check out all our tips about how to spend a multi-day trip to Florence.

2. The tower city, San Gimignano

San Gimignano is one of the best preserved medieval towns in Italy. No wonder it is on the UNESCO World Heritage List. San Gimignano is known as the tower city; From afar you can already see 14 – of the original 72 – towers rising above the town. The missing towers were destroyed during wars between the 12th and 14th centuries. The (residential) towers used to be a status symbol. Noble families showed their prestige with the height of the tower. To get to know everything about San Gimignano and go to all the highlights, towers and museums you can get the San Gimignano pass.

Within the town walls there is a cozy and authentic atmosphere. The square Piazza della Cisterna, named after the water well, is the heart of San Gimignano. Pick a spot at one of the many terraces and eat the most delicious ice creams at Dondoli. You can choose from many special flavors, such as Limoncello! Tip: Walk into one of the narrow side streets every now and then. From here you can spot jaw dropping viewpoints over the rolling hills of Tuscany.

3. Historic Siena

With its special architecture, basilica, Gothic cathedral, palaces, statues and squares, Siena is a real must-see during your road trip through Tuscany. A popular sight in Siena is the shell-shaped square Piazza del Campo. It is the connector of all main streets and there is a warm atmosphere. Admire the Fonte Gaia fountain and see imposing important buildings such as the City Hall. Twice a year the spectacular Palio di Siena horse race is organized here. The square gets transformed into a horse racing track and the different districts of Siena compete against each other!

4. Popular Pisa

Pisa is very touristy and that is mainly because everyone wants to admire eye-catcher number 1, the leaning bell tower of Pisa. The tower is on the square Piazza dei Miracoli that means the Square of Miracles and has been declared a UNESCO World Heritage Site. Buy your tickets here in advance. There are even more impressive buildings on this square, such as the largest Baptistery in Italy, Cathedral of Santa Maria and the cemetery Camposanto. Besides the special architecture, Pisa also has one of the oldest botanical gardens of Europe, there are plenty of shops to look around and you can take a lovely walk along the river Arno.

Combine Pisa with a trip to the beautiful surroundings. In 20 minutes you drive to Lake Puccini, where you enjoy the peace and beautiful lake.

5. Cozy Lucca

Lucca is surrounded by a city wall that has remained completely intact. The oldest parts even date from the 2nd century BC! Within the city walls, there are many churches that will impress you: the San Michele in Foro, San Giusto and Chiesa di Santa Maria Forisportam. But the most notable sight is the round square: Piazza dell’Anfiteatro. This square is built on the ruins of a Roman amphitheater. Now it is full of cozy terraces; where you can fully enjoy the Italian hospitality. Lucca is also a perfect shopping city. There are lots of well-known international clothing chains and local Italian boutiques.

6. Undiscovered Arezzo

Arezzo has a beautiful historic center. The nice thing about Arezzo is that the city is not very touristy, so you can explore the city in peace and experience the local life! Admire the Romanesque and Gothic architecture on a city walk or visit its cathedral and museum. And walk through the atmospheric streets towards the sloping square Piazza Grande, which impresses you with the surrounding old buildings. Take a seat on one of the terraces where you can have a delicious lunch. Full of energy again? End the day with a walk through the city park, where you can reminisce about all the impressions of the city.

7. Hill town Volterra

Volterra is located on the top of a hill and is surrounded by a city wall. Be surprised by the culture, the panoramic views of Tuscany and the impressive city gates. There are plenty things to do; visit the Roman theatre, cathedral, one of the museums or art studios. In the heart of the city center you will find one of the oldest town halls in Tuscany; Palazzo dei Priori, built in 1208. See the ancient halls from the inside or climb the bell tower to see Volterra from above.