Unmissable Itinerary in Tuscany!

Tuscany, a region beloved by many Brazilians, has spectacular places that are famous all over the world. Whether because cities like Florence and Siena are in it or because of the wine production in cities like Montepulciano or Montalcino. Since there are so many options of cities and places, it is always good to have an itinerary to follow and avoid the risk of feeling lost. In our post today, we have prepared an unmissable itinerary for you to make the most of your time in beautiful Tuscany. Stay with us and make the most of the boot country! Here at Italy’s Dream Tourism you can make the trip of your dreams come true!!! Also check out our Accommodation in Italy Section – Tips for your Vacation!

Our Introduction

Traveling around Tuscany is truly an unforgettable experience for anyone. Its landscapes, works of art and culture allow us to immerse ourselves in a beautiful world, adorned with cypress trees, flowering fields and mountains.

Our itinerary will be partly by train and partly by car. The train will save you time, but the car part will allow you to enjoy the scenic details of the roads between one city and another in greater depth. The idea is to arrive in Italy via Rome, and then take a train to Florence, as that will be our starting point. Ready to get started? Read also: What to see in Italy in twenty days by car?

1) Unmissable Itinerary in Tuscany! FIRST DAY – FLORENCE!

We couldn’t start our itinerary in a better way. The City of Arts is a city that is usually never left out of a tour of Italy, and it’s no wonder that this happens, because the city has a very pleasant energy, starting with the number of inhabitants. It is not as big as Milan or Rome, as it has around 367 thousand people living in the city, which already makes us feel more cozy. In addition, wherever you go, there is a sculpture, a story, artists performing or painting canvases with their paints and fascinating colors. We will spend three nights in Florence. Also read our post Where to sleep in Florence?

Attractions in Florence for the First Day

On this first day in the city, we will visit some of the main tourist attractions. We will start at Piazza del Duomo and there we will already have the Basilica of Santa Maria della Flor, Giotto’s Bell Tower and the Baptistery of San Giovanni. Another advantage of Florence is that its main attractions can often be reached on foot, and it is truly delightful to walk around the city streets. Piazza della Repubblica and the Church of Orsanmichele are places we will also visit on this day, a place with shopping streets and full of little shops. Continuing in this direction, we will arrive at Piazza della Signoria, a beautiful place that has a replica of Michelangelo’s statue of David.

And to end the day’s tour, we will go to Palazzo Vechio, which is the administrative heart of the city, where the Florence government headquarters is located. Afterwards, the ideal thing to do is enjoy a nice dinner at a nearby restaurant and go to rest, because the next day, we will continue in Florence, to enjoy a little bit of the Florentine air! Read also: How many days should I stay in Florence and what should I see?

2) Unmissable Itinerary in Tuscany! SECOND DAY – FLORENCE!

Yes, one day is not enough to admire and get to know the city. Therefore, we decided to stay there for another day and visit other tourist attractions that would enrich your stay in beautiful Florence!

Attractions in Florence for the Second Day

After a lovely breakfast, we will visit other gems of the city. The city that was ruled by the Medici family for a long time still benefits from the “legacy” left by them. The Medici Chapel is one of those places that deserves to be visited. To give you an idea, all the tombs there were simply made by Michelangelo, so we already have a small idea of ​​the importance of the Medici, don’t we?

Speaking of famous Italian artists, how about seeing a work by Giotto? Well, in the Basilica of Santa Maria Novella, there is a crucifix painted by him, as well as a wooden crucifix carved by Brunelleschi and the Trinity by Masaccio. After this incredible tour, we will go to one of the city’s postcards, the Ponte Vecchio, a beautiful place, and where you can have a beautiful view of the city from either of the two observation points. The Palazzo Pitti is the next stop, an incredible palace where you can visit museums and an art gallery, with masterpieces by Titian and Raphael.

We will end our day and our visit to Florence by going to the Boboli Gardens, a true living picture, which was part of the Medici residence; woods, alleys, and sculptures decorate this fascinating place.

There is a place that is worth visiting if you want to see it and are not too tired, especially if you want to see a spectacular sunset: I am talking about Piazzale Michelangelo, a place that allows us to have a magnificent view of the city.

Then, choose a good place to have dinner and rest, because the idea is to get up early and head to the cities of Pisa and Lucca! Read also: What to do in Florence in two days?

Golden Tip!

Even though Florence is smaller than other cities, that doesn’t mean it isn’t crowded with tourists, so it’s essential to buy entrance tickets to the main tourist attractions in advance, so it’s important that you know how to buy these tickets. Find out more by reading our post Tickets to the main monuments in Italy.

3) Unmissable Itinerary in Tuscany! THIRD DAY – DAY TRIP TO PISA AND LUCCA!

Our third day will be a day trip from Florence. We will start by leaving for Pisa, we will go by train. The trip takes about 1 hour and it is best to leave from Santa Maria Novella Station, as there are direct trips, without having to change trains, which will make your life easier. Oh, and remember to buy your tickets in advance through the Trenitalia website. From Pisa, we will take another train to Lucca, the trip takes on average 30 minutes. And after enjoying this beautiful city, we will return to Florence. Read also: How to get to Pisa from Florence?

Attractions in Pisa

When we talk about this city, everyone thinks only of the Leaning Tower, and it really is the one that arouses the most interest among tourists. But the city has other attributes that deserve a loving look, such as Piazza dei Miracoli, Camposanto, Lungarni and the Cathedral of Santa Maria Assunta and the Baptistery of San Giovanni. You see, there are other cool places to visit in Pisa. Read also: What to visit in Pisa in one day?

Attractions in Lucca

Lucca is a charming city, and many people often leave it out of their itinerary of cities to visit in Tuscany.

A city surrounded by walls, which is already a great attraction in itself, has many flower-filled squares, lots of trees and charming tourist attractions, such as the Historic Center where you will see the Cathedral of San Martino, Piazza dell’Anfiteatro, Piazza Napoleon, known by the locals as “Piazza Grande”. Oh! Don’t forget to visit the Mansi Palace. The city also has several medieval towers, and the two main ones are the Giunigi Towers and the Tower of Hours, which will allow you to have an incredible view of the city. Read also: What to do in Lucca in one day?

After this incredible day in these two cities, we will return to Florence, the trip takes approximately 1h30. Arriving in the city, have dinner and rest, as we will leave for Volterra early in the morning.

4) Unmissable Itinerary in Tuscany! FOURTH DAY – VOLTERRA AND SAN GIMIGNANO!

The day has dawned, we will leave Florence and take the train to the city of Volterra. The trip between one city and the other will take approximately 3h30. Note that in Volterra you will already start using the car, and it is very important that you rent it in advance, to avoid stress. On this day, we will also visit San Gimignano and sleep in the Chianti region.

Attractions in Volterra

The city gained a lot of notoriety after the film Twilight, but it was famous long before that. It was one of the most important cities in Italy between the 4th and 6th centuries, and even today we can see how powerful it really was, with its walls and buildings built until the beginning of the Middle Ages.

The main tourist attractions are the Duomo, the Etruscan Museum of Guarnacci, the Walls of Volterra, the Etruscan Acropolis, the Medici Fortress, the Porta Selci, the Pinacoteca and the Alabaster Ecomuseum. Another place that you can’t miss is Piazza dei Priori, the most important in the city. Read also: Let’s get to know Volterra in Tuscany?

Attractions in San Gimignano

A medieval city worthy of Oscar-winning films, that’s how I define San Gimignano. Its beauty is so great that the city is a UNESCO World Heritage Site. Over the years, San Gimignano has changed little from the 14th century to the present day.

The city has managed to keep 13 tower houses intact, which has become the great characteristic of the place. These houses are connected by bridges, which in the past were used so that people could get from one place to another without having to go out into the street, as there were many suspicious people on the streets, as well as other problems (fights and political or family feuds). Therefore, it was better to cross the bridges that connected the houses.

In addition to the tower houses, in San Gimignano you can’t miss a visit to the San Gimignano Cathedral and the Palazzo Comunale, which is right next door, where you can find the Pinacoteca di Arte Medievale. Through the Civic Museum you can visit the Torre Grossa, which is 54 meters high and is the symbol of the city.

Want to enjoy a good wine? Then you should try the white wine produced there, with the Vernaccia grape; it will be an unforgettable experience!

After getting to know and enjoying the charms of these two cities, I suggest you head to the Chianti region, which is approximately 23 km from San Gimignano. Read also: Why visit San Gimignano?

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Advantages of traveling with a rental car

• If you are traveling with 2 to 5 people, it is the most economical option! You just need to choose the places to visit calmly and leave with peace of mind! Always have a map with you, or opt for a car with GPS; not all cars have this option! Oh, and your cell phone can be a problem if you pass through a place without an internet signal.

Disadvantages of traveling with a rental car

• Unforeseen expenses with parking and fuel that, unfortunately, cannot be calculated, but this is normal. In my opinion, the biggest disadvantage is the lack of knowledge of the territory, which can sometimes result in wasting time finding the main cities, and turning an enjoyable trip into a nightmare!
• Generally, those who drive are unable to enjoy the beautiful views around them.

5) Unmissable Itinerary in Tuscany! FIFTH DAY – CHIANTI!

Many people think that Chianti is a city, but it is actually a little piece of Tuscany, in a mountainous region between the cities of Florence, Siena and Lucca, in other words, a splendid location

The production of high-quality wines is the highlight of the region, there are numerous wineries there, with their stunning and refined structures, with tastings, delighting you with all the quality of good wine and good Tuscan food. In addition, there are several castles and agritourisms where you can stay in the region.

Important!

We will also sleep in Chianti for four nights, and to help you choose where to stay, also read our posts: 5 Castles to stay in Chianti in Tuscany and Agritourisms to stay in Tuscany, they will be very useful for you!

Attractions in Chianti

There are some small towns that stand out and are worth visiting, such as Greve in Chianti, with its churches and parishes and castles that were once the residences of nobles. You will find many crafts and typical Chianti foods near the squares in Greve Chianti.

Another town worth visiting is Montefioralle, the birthplace of Amerigo Vespucci; the house where he was born is identified with the family coat of arms. It is a very small town, there is not much to see, but due to the stunning views and its atmosphere of genuine Italy, Montefioralle is part of the Club of the most beautiful villages in the country.

How about tasting a real and delicious “bisteca alla fiorentina”? Well, in the town of Panzano in Chianti, more precisely at the Antica Macelleria Dario Cecchini (former butcher shop), you can enjoy this incredible typical dish. In addition to these three cities, we also have Castellina in Chianti and Radda in Chianti, which are among the main towns in the region. Want to know more about Chianti? Then read our post: What are the main locations in Chianti in Tuscany?

6) Unmissable Itinerary in Tuscany! SIXTH DAY – DAY TRIP TO SIENA AND MONTERIGGIONI!

Our sixth day will be spent visiting two more magnificent cities, Siena, which is known all over the world, and Monteriggioni, a charming city that many people have never even heard of. The distance between them is only 15 km, so if you are driving, you will be able to visit both cities without any problems, take a day trip and return to sleep in Chianti.

Attractions in Siena

A place that most people make a point of including in their travel itinerary for Italy, as history, art and lots of tradition are part of the culture of this city.

Among the attractions that are worth visiting, we can highlight the Piazza del Campo, beautiful with its tower, the Civic Museum and the Mangia Tower, the Cathedral of Siena, the basilicas of San Francesco and San Domenico. In addition to enjoying the beautiful walks through the city streets, which are truly enchanting. Read also: What to visit in Siena in one day?

Attractions in Monteriggioni

Monteriggioni is still off the beaten tourist trail in Italy, but it is simply beautiful. It has about 8,000 inhabitants and is also medieval in style, as it was founded in the mid-13th century. It is located on top of a hill and is surrounded by walls that command respect, and around these walls the landscape is completed with olive trees and vineyards.

Right at the entrance you will be greeted by the “Porta Franca” that will lead you to Piazza Roma. Other tourist attractions that you can visit are the Museo Monteriggioni in Arme and the Pieve (Church) of Santa Maria Assunta.

The city lives so much the medieval atmosphere that usually in July, a festival takes place where the residents sing, dance, play instruments and dress up in period costumes, a real spectacle! After this special day, it is time to return to Chianti and rest, because the next day there are more beautiful places to visit. Interested in Monteriggioni? Then read our post Why visit Monteriggioni in Tuscany?

7) Unmissable Itinerary in Tuscany! SEVENTH DAY – DAY TRIP TO MONTEPULCIANO AND PIENZA!

Today the day will be graced with a visit to these two fabulous cities in Tuscany. These cities allow us to enjoy stunning landscapes with their valleys and cypress trees.

Attractions in Montepulciano

Known for the production of its “favorite” wine, the Vino Nobile, known throughout the world. But Montepulciano has other charms, for example, Piazza Savonarola, where the small church dedicated to Saint Bernard is located. The Tempio di San Biagio and the Chiesa di Santa Maria dei Servi (the oldest in the city) are also worth a visit. Read also: Discover Montepulciano and its fantastic wine!

Attractions in Pienza

Want to visit a city that is synonymous with tranquility, then you have found it, Pienza. Another beautiful UNESCO World Heritage Site, the organization of its buildings and the conscious use of its spaces draw the attention of those who visit it.

The Piccolomini and Borgia palaces, the Santa Maria Assunta Church and the Pieve di Corsignano Church are the tourist attractions to visit. Want to know more about Pienza? Then read our post: Let’s visit Pienza in Tuscany?

After this spectacular day, return for your last night in Chianti, have dinner, relax and enjoy the wonderful night that the air of this region provides.

8) Unmissable Itinerary in Tuscany! EIGHTH DAY – MONTALCINO AND SAN QUIRICO D’ORCIA.

On our eighth day, say goodbye to Chianti early and leave for Montalcino, which is 81 km away. There we will sleep the last two nights of this ten-day itinerary. You will experience more wonderful moments in these last days, including visiting the place where the wonderful photos of Tuscany that circulate around the world are taken. You will experience this moment in San Quirico d’Orcia.

And of course, we can’t forget to remind you that you will also taste Brunello di Montalcino wine, a jewel in the world of wines! So in Montalcino and San Quirico D’Oricia, you have nothing less to expect than excellent wines and cinematic landscapes. Also read our post with tips on Wineries to Stay in Tuscany.

Attractions in Montalcino

A very welcoming and pleasant city with around 5,000 inhabitants, right in the heart of Tuscany, Montalcino is known worldwide for the excellence of the wines it produces and its flagship is Brunello di Montalcino, but in addition to enjoying this incredible drink, you should also take a stroll and visit places such as Fortalezza Rocca, the Clock Tower and the Duomo. Learn more about Montalcino in Let’s visit Montalcino? The famous city of Brunello!

Attractions in San Quirico d’Orcia

The town’s privileged location, on top of a hill, makes the region’s views stunning, so much so that many of those famous photos of Tuscany, with cypress trees and little roads in the middle of the fields, are taken in the town. The Church of Santa Maria Assunta, the Horti Leonini Garden and the Torre del Cassero, the Porta Cappuccini and the Chapel of Vitaleta, are places you’ll enjoy visiting. 

9) Unmissable Itinerary in Tuscany! DAY NIN – DAY TRIP TO CORTONA AND AREZZO!

History and beauty are part of the daily life of these cities. Both Cortona and Arezzo are located on hills, which offer beautiful views. Arezzo is a larger city with about 100,000 inhabitants and Cortona has about 20,000. But in terms of beauty, both win our hearts.

Attractions in Cortona

Art and history are strongly present in Cortona, starting with the city walls from the 4th century BC, the Fortezza del Girifalco, from 1556, Piazza Della Republicca, Palazzo Del Capitano Del Popolo and the Church of Sant’Agostino are the attractions you will have in the city. Oh, there is also Piazza Signoreli, which on Saturdays has a super cool little market to visit. Learn more about the city by reading our post: What to do in one day in Cortona?

Attractions in Arezzo

One of the main cities in Tuscany, Arezzo is a city that everyone who visits is enchanted by and wants to return to. It is very pleasant to stroll through its streets, learn about its history and enjoy its routine.

Piazza Grande is beautiful and full of restaurants, bars and shops that make the place lively. Speaking of activity, it is precisely in this square that a medieval duel called Giostra del Saracino takes place (don’t be scared, it is all staged). The event takes place in June and September. It is also in this square that the largest antiques fair in Tuscany takes place, the Fiera Antiquaria di Arezzo, where you will see beautiful pieces!

Other places to visit are the Museo Archeologico Mecenate, the Cappella della Madonna del Conforto, the Fortezza Medicea, the Palazzo Comunale and the Duomo. Are you curious to learn a little more about Arezzo? Well, read our post: What to do in one day in Arezzo?

10) Unmissable Itinerary in Tuscany! DAY TEN – SATURNIA THERMAL BATHS AND PITIGLIANO!

On the last day of our itinerary, you will leave Montalcino early and head to Pitigliano, 81 km apart from the two cities. After getting to know this interesting city, you will sleep in Saturnia Thermae, which is 31 km from Pitigliano. A wonderful place, and I can assure you, it is everything you need to end your trip with a “Golden Key”.

Attractions in Pitigliano

In some places in Brazil, the name Pitigliano is given to pizzerias, but what most people don’t know is that the real city that bears this name has an incredible history and is known as the Italian Jerusalem, because in the 16th century there was a large Jewish community. In fact, the city has a Synagogue that houses several rooms with permanent exhibitions that tell the story of Jewish history.

Other interesting places to visit are the Cathedral of Pitigliano: in Piazza San Gregorio, the Fountain of the Seven Spouts, the Palazzo Orsini, the Alberto Manzi Open-Air Archaeological Museum and the Vie Cave di Pitigliano. Pitigliano is undoubtedly an incredible city with a very rich and deep history, it is worth visiting! 

Attractions in Terme di Saturnia

I believe that you may be a little tired at this point in your trip. So how about a relaxing bath in thermal waters, to help you relax and prepare your body and spirit to end your trip and return to your routine? Well, as I said, you will sleep the last night of the itinerary there, and you will not regret it.

Terme di Saturnia is simply a wonderful spa! Waters with constant temperatures of 37.5°C, which spring from the depths of Mount Amiata. Restaurant, showers and of course hotel are part of a great structure to welcome you. But be careful, the place is open all year round, but it gets crowded, especially in the summer, but if you book in advance you can enjoy this place and relax before returning to your routine! Learn more about the Terme di Saturnia in our post Let’s visit the Terme di Saturnia in Tuscany?

Well, that’s the end of our 10-day itinerary with this Unmissable Itinerary through Tuscany! If your trip ends here, I suggest that you start the day at Terme di Saturnia and drive to Rome, which is 153 km away.

ATTENTION!!

When you arrive in Rome, return your car at the airport, as Rome has a Limited Traffic Zone and the chance of getting a fine is very high, so WE DO NOT ADVISE ENTERING ROME BY CAR.

Golden Tip!

The itinerary we mentioned is just one of the many possible itineraries for traveling around Tuscany. Do you want to change a city, stay longer or shorter in one place or another? Great, no problem! But if you need help organizing your trip to this beautiful region or any other place in Italy, count on me and my team! Whether it’s to create a new itinerary, help you choose hotels, transfers, tour guides and much more! We specialize in making your dream of traveling through Italy come true! 

Are you interested? Click here and contact us!

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Conclusion

Unmissable Itinerary in Tuscany! The Tuscany region is a place that everyone knows has unique beauty and being able to explore it on an itinerary like the one we present to you will make your trip even more special, with lots of knowledge, cultural enrichment and unforgettable memories!

Do you feel insecure traveling?

If you need help organizing your trip, do not hesitate to contact me! I would love to help you make your dream trip to Italy.

Did my post help you, or do you still have questions? Leave your comment below, and I’ll get back to you!

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