Tuscan holidays: choose your next Tuscany destinations!
week end in toscana

Tuscan holidays are within everyone’s reach! Let’s discover breathtaking landscapes, picturesque villages and culture. Every season is perfect for your holidays in Tuscany!


Never spent your holidays in Tuscany? What have you missed until now! Whatever your travel desires are, Tuscan holidays can satisfy them all and at any time of the year.

With breathtaking landscapes, amazing villages, spas and events available all month long, including the Christmas markets, you can’t have any more excuses. As we all know, Tuscany is home to many famous poets, artists and extraordinary minds, proclaiming itself a land of culture and art without equal.

Now that I’ve got you curious, this guide will give you more than enough reasons to switch off your brain and head for the land of art and good food, admired and envied in all corners of the world.

I bet your mouth is watering thinking about fiorentina steak (in Italian, bistecca alla fiorentina), paired with a good glass of wine, isn’t it? So let’s set off together on this magnificent journey through your next Tuscany destinations! 😍


Are you fascinated by Tuscany? Check out all the travel ideas!


Some ideas for unforgettable Tuscan holidays

As I said, there are plenty of ideas for fantastic holidays in Tuscany! That’s why I will guide you step by step and in great detail, presenting many interesting places to visit in Tuscany, divided by province. You will be enraptured by the beauty of these territories and the immense number of activities.

Whether you are a nature lover, have a desire for adventure or simply to relax, all this can be satisfied through hiking, horse riding or cycling routes. But you can also choose purely recreational activities, thanks to spas or yoga classes.

If you don’t know where to go in Tuscany, I suggest you to find out by reading, you won’t regret it! You will also find many interesting holiday packages 👇


1. Florence and province

You must put it first on the list. Short breaks in Florence are a must for everyone, even more so for art and food lovers. Filled with must-see attractions, you can enjoy an aperitif on Ponte Vecchio bridge or visit the spectacular monuments by the main protagonists of Italian art history: Michelangelo and the square built in his celebration, but also Brunelleschi, creator of the magnificent dome of the city’s Duomo.

This city exudes art and antiquity, and you’ll notice this as you walk through the streets and stand speechless in front of attractions of all kinds: from Palazzo Vecchio to Palazzo Pitti, entering the Uffizi museum and the church of Santa Maria Novella.


tuscan holidays


The art and culture would be endless, so I’ll tell you about its food and wine! For your Tuscany breaks, while you are in Florence, the Antico Vinaio is a must to eat the best stuffed focaccia in town. You should also know that the Antico Vinaio has recently opened a new restaurant in Rome.

Another curiosity for video game lovers: if you love video games, you will know that this city was used as the setting for the plot of the very famous game “Assassin’s Creed II”.

During unforgettable Tuscany short breaks, you can visit the Chianti region! It is a very famous destination in the province of Florence, known throughout the world for its lovely vineyards and fine wine, with D.O.C.G. label.

The peculiarity of this area between Florence and Siena lies in its evocative countryside, characterised by wonderful villages, castles and vineyards.

The area includes the municipality of Greve in Chianti, overlooked by the castle of Montefioralle, but also Rufina and Panzano, where you can find the Antica Macelleria Cecchini, an undisputed destination to buy top-quality meat.

Not to mention Certaldo! Italian writer Giovanni Boccaccio was born here: you can go and see his house, if you wish. And before returning home after these holidays in Tuscany, try a traditional local dish, the famous tripe and lampredotto!


2. Siena and province

When it comes to Tuscany destinations, this region has a lot to offer even in the province of Siena! I recommend a holiday to medieval Siena! The city is characterised by its particular brown colour that you find in the streets, on the palaces and on their roofs.

The Piazza del Campo has been the heart of the city since 1300. It is here that the Palio di Siena, with its ancient traditions, is held two days a year. The 88-metre-high Torre del Mangia, flanked by the Palazzo Pubblico, also stands out in this square.

But that’s not all, if you visit the baptistery and the cathedral you will realise how much culture surrounds this city. You will get to know the famous painters and artists who shaped it, including Donatello and Jacopo Della Quercia. As well as its courtly atmosphere, Siena also proves to be a bustling and lively city, full of young university students.

For magic holidays in Tuscany, you must visit Montalcino, located in a fairy-tale countryside landscape where fine Brunello wine is produced. In its ancient fortress you can attend the Jazz & Wine Festival, which takes place every year in July.

If you have time, you can stretch out to Montepulciano. In ancient times, this town was fought over by the Florentines and Sienese because of its geographical position, ideal for trade. Its economy revolves around the wine industry and the town is worldwide famous for its Vino Nobile di Montepulciano D.O.C.G..

Not to be missed are the nearby villages of San Gimignano, known for its Vernaccia and its saffron PDP, as well as Rapolano, where you can relax at the thermal baths.


3. Lucca and province

This magnificent city of art and craftsmen delights you from the first moment you set foot in its historic centre. Lucca offers all sorts, which is why short holidays to Tuscany Italy may not be enough. Dozens of events take place every year, including the Lucca Film Festival, Lucca Comics & Games, LuccAutori and the Lucca Summer Festival.

The Cathedral of San Martino and a few walks along the walls surrounding the historic centre are a must, without depriving yourself at lunchtime of a nice Tordello lucchese, a type of traditional tasty stuffed egg pasta.

For Tuscan holidays in the province of Lucca, you must pass through the Garfagnana. You will find yourself surrounded by wild nature, chestnut and beech woods: a great way to breathe clean air far from the big cities, where the atmosphere is magical.

I recommend you also go to Forte dei Marmi, an elegant tourist area visited by VIPs from all over the world. Here you can relax by the sea, pampered by all the comforts, on a coastline of fine sand. Alternatively, there is Viareggio, which I strongly recommend visiting during the Carnival period.

If you pass through the province of Lucca, you should absolutely eat these dishes: Buccellato, sweet bread with sultanas and aniseed, but also potato bread and Necci. They are similar to cannoli, but made with chestnut flour. The filling can also be salty.


4. Livorno and province

Looking for the best Tuscan holidays for you and your better half? Fly to Livorno for two days or more. This dynamic city overlooking the sea has been transformed into a port since the Renaissance period, welcoming a large number of personalities, including merchants and prominent political figures.

The Fortezza Vecchia represents Livorno’s history, originally built as a defence system against Saracen invasions. The newer Fortezza Nuova is located in the La Venezia district, so called because of the dense network of canals that bring water to the fortress.

For holidays in Tuscany dedicated to good food, you can’t miss its culinary traditions, including raw fish and Cacciucco, a fish-based soup. These recipes are strongly linked to Livorno’s maritime tradition.

Away from Livorno city, you can stroll through charming medieval towns such as Castagneto Carducci and Bolgheri, known for its Sassicaia. This fine wine has received top international awards and raised our nation’s flag high.

If the idea is to have a summer holiday, I recommend two great Tuscany destinations: Giglio and Elba islands. Here you will find some of the most beautiful beaches in the whole country.


5. Grosseto and province

As a city that combines history and charm within a mighty city wall, Grosseto is an excellent choice for your holidays in Tuscany.

In Piazza Dante, the soul of the city, stands the cathedral of San Lorenzo. This is the architectural result of various eras that have followed one another since its initial construction in 1300. However, the marvellous church of San Pietro is even older and well worth a visit.

In Grosseto you also come into contact with the past in the surrounding villages. In Pitigliano, for example, an Etruscan community settled in the sixth century. Thus, this small village retains its mysterious aura.

But here too there is an interesting offer that ranges from thermal baths, as in Saturnia (a must for spa lovers), to the sea in Monte Argentario, which is however quite expensive. But from this you can understand that it is one of the best places in Tuscany.

We also talk about food and wine by mentioning Seggiano, a picturesque village where they produce such a good extra virgin olive oil that it has obtained the PDO certification.

We come back to the same point: if you want to spend good short breaks Tuscany is a must!


6. Massa Carrara and province

Carrara, we know, reminds us of marble. Worthy of being called white gold, Carrara marble has origins dating back to Roman times and is now known worldwide.

Here you can stock up on Lardo di Colonnata PGI and immerse yourself in nature in the middle of the Apuan Alps. I guarantee you unique holidays in Tuscany! But I suggest you read on to discover other breathtaking places to visit in Tuscany and incredible culture!


7. Pistoia and province

Pistoia is a great idea for your Tuscany short breaks, where you can eat well and relax at the spa!

This small town can be visited entirely on foot and fascinates travellers with its complex architectural appeal, not surprisingly it was named Italy’s capital of culture in 2017. With evocative monuments such as the Piazza del Duomo and the Church of San Giovanni Fuorcivitas, Pistoia should be among your Tuscany destinations!

At the end of August, pastry shops will be selling pippi and corone. These biscuits are alternated with Pistoia chocolates and sugared almonds in such a way as to create a shape reminiscent of a necklace.

On the other hand, if you are looking for tranquillity, I suggest you go to Montecatini, a well-known spa town where you can get rid of the daily stress.


8. Pisa and province

Famous all over the world for its Tower that leans 4 degrees to one side, Pisa is visited by many tourists all year round. It is therefore an excellent idea for your holidays in Tuscany!


tuscany breaks


The place where the tower stands is the Piazza dei Miracoli, a UNESCO World Heritage Site. The square is also home to the marvellous Cathedral of Santa Maria Assunta and the Baptistery of San Giovanni, where Galileo Galilei was baptised.

If you are a nature lover, don’t miss the WWF oasis of the Tanali forest, where you can also be accompanied by a guide.

But Pisa offers even more! In addition to San Miniato, a small town where the white truffle festival is held every year, in the province of Pisa there is Volterra. This medieval town is a place rich in culture with churches, historical buildings, museums and imposing walls.

Haven’t I convinced you yet to spend unforgettable holidays in Tuscany? Then I invite you to finish reading! Maybe you still have time to choose between fantastic places to visit in Tuscany!


9. Arezzo and province

When you arrive in this city, you immediately breathe in an artistic and intellectual air, passing by the Duomo and Piazza della Libertà, finally arriving at the park surrounding the Medici fortress.

Many traditional dishes are served in this town, including steak with anchovies in salt, grilled and seasoned livers and Scottiglia, a stew prepared with different types of meat.

Other small, ancient villages frame this beautiful city. One example is Lucignano: it gives the impression of being immersed in medieval times, among dwellings made of brick and stone. Anghiari and Cortona even date back to Etruscan times, as the valley where the latter village is located was called “the granary of Etruria”.


Holidays in Tuscany, with gusto!

There is a reason why Tuscany is so important to the wine industry. In fact, when poor-quality wine was being produced all over Italy until the end of the 1700s, Bettino Ricasoli, a Tuscan entrepreneur, decided to travel to France to learn the most modern wine-making techniques, with the aim of bringing them back to his homeland.

This made it possible to produce top-quality Chianti wine, suitable for export to other countries.


best tuscany holidays


Tourists who stay in Tuscany, a land that instils emotions and positive memories, always leave with a bit of nostalgia from this region that has so much to offer, where good food and wine are not lacking!

If you are passionate about this incredible land, I really hope you enjoyed this short guide! What are you waiting for to spend your Tuscan holidays? With Italia Delight, you can choose the best Tuscany destinations and organise your trip, even a tailor-made one, with Local Experts!


About Author

Stefano Valenti
Ciao, sono Stefano! Sono laureando alla facoltà di Scienze e Culture Enogastronomiche a Roma Tre. Cerco sempre d'infondere la passione in ciò che faccio, in particolare in cucina, dove adoro giocare con le ricette.


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