• Tuscany in 5 Days
  • Day Trip: Discover Pisa
  • Day Trip: Discover Siena

 

Tuscany in 5 Days - flavors and emotions
Tuscany is one of the most beautiful regions in Italy, with medieval villages sitting atop hilltops, rolling hills covered in vineyards producing some of the best wines in the world and farmhouses and villas at the end of cypress-lined lanes. There are many things to see and do in the region, the hard part is really deciding how to fit everything into the days you have at your disposal!
Five days is right about the perfect amount of time we recommend you dedicate to exploring this beautiful region and a car will be required. As we suggested in our 5 day itinerary for Tuscany, take Florence out of the equation and dedicate one day walking Florence or even two full days.  Better yet have a look at our three day itinerary for exploring this exciting city.
Some parts of Tuscany can be reached with public transportation but many of the small villages waiting for you to be explored are not. Ready? Go!

Day 1: Pisa and Lucca
YOn your fisrtd day, pick up your car and head to Pisa in the morning to explore the famous Piazza dei Miracoli, where you'll be able to finally admire the famous Leaning Tower up close. Take time to visit the inside of the Duomo, the baptistery and Camposanto. Here's an idea of what else you can see in Pisa in a day, if you want to spend a little more time exploring this "college" town and don't miss to take a picture on Lungarni, along Arno river.
After a nice lunch, head to Lucca for the afternoon. Lucca is a small Venice without water, enclosed within huge Renaissance walls which today have become a park: rent a bicycle to explore and view Lucca from every angle from the added height of the walls. Take a walk through the historical city center, and go see the Duomo, the peculiar oval-shaped Piazza dell'Anfiteatro and climb to the top of the Guinigi tower with its curious centuries old trees at the very top!

Day 2: Chianti
The area between Florence and Siena is the beautiful Chianti region, famous for its excellent red wine worldwide. Vineyard-covered hills alternate with olive groves, each bend in the road offering a panoramic view of the wine region.
Starting from the north, take the Via Chiantigiana (SS222) and stop in Greve in Chianti to explore its peculiar shaped square and all of the shops in its perimeter. Visit the Wine Museum if you have some time, more for the chance to taste over 200 wine labels of the region than for the farm equipment. Continue along to Panzano in Chianti, stopping to walk along its ancient city streets and take pictures of the hamlet, then on to Castellina in Chianti to walk around the small center and through the city walls. Wine tasting in this region is obligatory – the difficult part will be deciding where! There are wine shops in each town, but also signs along the road will signal wineries and their shops where you can taste that estate's wines. Stop at any that catches your fancy as this is Chianti Classico DOP region and you cannot go wrong.

Day 3: San Gimignano
Enjoy the drive and incredible views of the countryside on the way for San Gimignano, stopping to enjoy the view of San Gimignano's medieval towers before you reach it. Enjoy the rest of the day here, as the majority of visitors leave this beautiful hilltop village as soon as the sun goes down giving you a chance to enjoy a quiet walk through its magical streets and stepping back in time. Make sure to taste the local specialty, the sandy colored Vernaccia of San Gimignano.
 
Day 4: Siena and Monteriggioni
If you step back into the Renaissance as you visit Florence, then Siena takes you back into the Middle Ages. The city center sits on several hills so expect some climbing but it is quite small and the main sights are close: start in the Piazza del Campo, famous for its particular shell shape and for the Palio of Siena, a horse race between the various parts of town run twice every summer on July 2 and August 16. The Palazzo Comunale and Torre del Mangia tower over the Campo, offering an impressive view of the square and the city if you climb all the way to the top. Head to the Duomo, standing majestically as a precious example of Italian Romanesque-Gothic style and admire the scenes across its pavement, a treasure waiting to be admired! Head back out to visit the Baptistery, crypt and Opera museum to see Duccio Buoninsegna's marvelous Maestà alterpiece from the 14th century. View our itinerary for a day in Siena for more ideas.

Just outside of Siena, the charming walled castle of Monteriggioni offers another trip into medieval times. The small castle still stands with 15 towers along the walls (although some of them were cut short through the centuries). You can visit the small castle, but don't forget to climb and walk along the massive walls from where you'll admire great views over the Tuscan countryside.

Day 5: the Val D'Orcia
The Val D'Orcia is another region in Tuscany famous for its stunning landscapes and excellent red wines. Gentle hills, dotted with dark cypresses, red poppies and yellow sunflowers make this region the perfect postcard to send back to friends and families. It offers plenty to see, from the medieval streets of Montepulciano to the smaller picturesque towns of Pienza, San Quirico D'Orcia and Montalcino. The area is known worldwide for its Brunello di Montalcino and Montepulciano DOC wines, making wine tastings an excellent past time at each stop.

 

A Whole Day To Discover Pisa - there is not only the Leaning Tower
Pisa is known worldwide mostly just for its Leaning Tower, but we encourage you not forget that there are many other reasons for visiting this wonderful city (just don’t ask what from someone who is from Lucca or Livorno, as the rivality that has existed for centuries between the three cities still exists today. A saying here says: Better a dead person in your house than a Pisan at your door!!).
First, getting to Pisa
If you choose public transport over driving, then you can avoid all the hassle of find parking and it is a easy choice since, since Pisa is very well connected to all of the main destinations in Tuscany. Train is by far the the easiest, fastest and cheapest way to get there. If you are nearby, in Lucca for example, you also have the option of getting there by bus, which will offer a more panoramic trip but if you only have one day at your disposal to visit Pisa, I recommend the train.
You can also drive to Pisa, of course, but do expect a bit of difficulty finding free parking near the Square of Miracles and there can be traffic, like many other cities.
A walking Tour Proposal to do on your own: let’s starts at the train station (since most of you will arrive by train or bus). Starting here also makes sense if you're already in Pisa if you spent the night here: you'll likely be in the city center, so you can head by foot to the square in front of the train station, but if you're in the surroundings, you can also just catch a bus and you'll likely be dropped off there as well.

1. Piazza Vittorio Emanuele & Lungarno Galilei
Outside the station, the first thing you see is Piazza Vittorio Emanuele, the administrative core of the city: this is an amphitheatre-shaped square surrounded by a circular, fully-pedestrian open gallery full of shops where several historical buildings look onto. Cross the square and head onto Corso Italia, the most important and renowned street of Pisa, a paradise for anyone that loves shopping!
Keep heading up the street, leaving behind Piazza del Carmine and Piazza della Pera to arrive at the famous Logge dei Banchi, just in front of Ponte di Mezzo on the Arno river (where the traditional "Battle on the Bridge" is usually celebrated). The Loggia, a characteristic and impressive covered open space was built according to a project designed by the famous Buontalenti at the beginning of the 17th century and used to offer shelter to the silk and wool market (from here comes its name, as banchi in Italian means stand as those found in markets).
Don't cross the Arno just yet and head to your right onto the Lungarno Galilei: the "Lungarni" are the roads that run along the Arno river, both in Pisa and in Florence, and are important streets for both residents and visitors alike. There are many cafes and restaurants along the river, and these streets are a popular meeting places for all who live in Pisa while for visitors it is the perfect place to enjoy a nice leisurely stroll and admire the architectural and historical treasures of the city. The Lungarni in Pisa show it's essence.
Before you arrive at the next bridge, called Ponte della Fortezza and crossing the Arno, I would like you to focus your attention on the unique San Sepolcro church, an octagonal building built as a refuge, a hospital and a monastery, dedicated to the Knights Templar.

2. Lungarno Mediceo & Piazza dei Cavalieri
Along the other side of the Arno, instead, runs the Lungarno Mediceo, known mostly for the Medici Palace also called Palazzo Vecchio (both Cosimo Il Vecchio and Lorenzo Il Magnifico lived here) and for the Church of San Matteo and National Museum, home to important works of art by internationally renowned Italian artists.
A few steps from there, we finally arrive at characteristic Borgo Stretto, a tiny medieval road surrounded by loggias and open galleries with small shops and stores that always catch the attention of people for taking you back a step in time!
As soon as the loggia ends on the left, turn onto this street and head toward Piazza dei Cavalieri, a place you need to pass on your way to the Square of Miracles. It isn't a large square, but is always crowded with people and students running from one place to another or sitting down and chatting somewhere. The piazza is home to the prestigious university Scuola Normale di Pisa and to the Clock Palace. This palace is characterised by two towers, one of which - the Hunger Tower - has been mentioned by Dante Alighieri in his Divine Comedy, and is thus widely known. Count Ugolino della Gherardesca, together with his sons and grandchildren, was imprisoned there and left to starve to death during the Middle Ages.

3. The Piazza Dei Miracoli
In less than 10 minutes from here, heading on to Via Santa Maria, you'll finally arrive at Piazza dei Miracoli, the Square of Miracles. As you approach, you will get the chance to catch sight of this marvellous place with its Leaning Tower and the other beautiful buildings that surround it - the Baptistery, the Cathedral and the Monumental Cemetery (representing the cycle of life).
The Cathedral is a wonderful example of Pisan-Romanesque architecture whose white-and-grey marble façade has been decorated with polychrome marble, creating a great first impact. The interiors, on the other hand, have been realized with white-and-black marbles. The bell tower, about 57 meters high, is known worldwide for its unintended tilt to one side. Why? The ground is too soft underneath! It is inadequate to support the tower's structure and weight and this was already evident from the very start, before it was even finished. Being in front of the Tower of Pisa is something really exciting! When I visit Pisa I loved standing in front of the Tower to admire it. Can you imagine what the square would look like if the tower was not tilted? I believe that it would lose some of its unique charm.
Can you imagine what the souvenir stands that surround the square would be selling instead? Do you think this place would have been famous on its own or would it have been one of those hidden secrets to be shared among art lovers and connoisseurs? The tower underwent many years of restoration to make sure the leaning stops and it doesn't end up falling on its side, and it was closed to visitors then... but now it is once again open and you can climb to the top! A climb I highly recommend as a once-in-a-lifetime experience to do in Pisa and considering that the number of accesses to the tower is limited, I suggest you consider buying tickets to get on the Tower in advance.
Would you ever have guessed that the Baptistery or the nearby Camposanto (a Gothic-style cemetery) are the most visited destinations of Italian high school students every year, exactly 100 days before the beginning of exams? Well, there’s a good luck ritual consisting of going around the Baptistery as many times as the mark you would like to get on your graduation exam... and it's also a very good reason to skip school for. If you happen to visit on that day and see really funny behavior from young students, you will understand what they are up to!
Facing the square you'll also find the Museo dell’Opera del Duomo, home to the several artworks and statues from the Cathedral and the Baptistery, and the Sinopie Museum. Entrance to all of the monuments require a ticket except for the Cathedral; you may buy tickets for just one or more monuments in the square (the tower is the only one that requires a separate ticket).

4. The Botanical Garden
Your day is not yet completed after your visit to the famous Square of Miracles. Now, located just 3 minutes walking distance from the Square of Miracles, you'll find the Orto Botanico or Botanical Garden of Pisa, a destination that brings a bit of nature into this artistic itinerary of Pisa. Instead of going back to the main train station where we’ve started our itinerary, you could save time and give your tired feet a break by heading to the other rail station in Pisa, Pisa-San Rossore. Here, you can take the train to Lucca and then on to Florence or to Pisa Centrale to change trains should you need to go elsewhere. If you decide to treat yourself to a last short break before going back home, take the chance to try one of the delicious restaurants in the old city center or along the Lungarni: there are many offering great, delicious Tuscan dishes at very reasonable prices.

A Whole Day To Discover Siena - a return to the Middle Ages
Siena is one of the most popular and visited places in Tuscany, a place extremely rich in history and art and with strong local traditions tied to its 17 districts (called “contrade”) and to the famous Palio di Siena, the biggest annual event that takes place twice each summer in the city. Located in the heart of Tuscany, Siena can be easily reached from the other cities in the region by car, train or bus. The city center is closed to traffic, so if you’re planning to arrive by car you’ll still have to move on foot or by public transport to visit Siena. The train station is located outside the city, but it is well connected with the city center by buses.
A day in Siena is certainly not enough to experience the city in all of its many sides, nor to visit all of its treasures. In a day, however, with a bit of organization, you’ll certainly be able to see the main attractions of Siena and to appreciate the charm and atmosphere of this lovely medieval town, probably leaving with the desire to return as soon as possible. If you have the time in Tuscany, do return for a second day!
If you visit Siena for the first time, I definitely recommend you to go straight into the heart of the city, to the beautiful Piazza del Campo, one of the landmarks of the city. You can decide to start your day in Siena right here or instead head towards the Duomo, returning to Piazza del Campo later. The main attractions of the city are located between Piazza del Campo and the Cathedral, so you’ll likely spend most of your time here anyway, but I  strongly recommend you to save some time to just stroll through the streets of the city, browse the shops, wander through the colors and emblems of the various contrade districts that you'll find hanging from the windows and doors of houses and more to get a sense of what daily life is in Siena.

1. Piazza del Campo
Piazza del Campo is truly unique with its shell shape, its bricks pavement and for all of the buildings facing on it. Standing at the center of the square, you can almost feel wrapped up in a warm embrace. Piazza del Campo hosts, twice a year (on July 2nd and August 16th), the famous Palio di Siena, the most anticipated, exciting event by all of the citizens in Siena. In the square, you can admire the Fonte Gaia, the largest fountain of the city originally decorated with sculptures by Jacopo della Quercia. The fountain as we can see today is a copy made in marble of Carrara marble, which is much stronger than the marble of the Montagnola used by della Quercia (the ancient Fonte Gaia ha been restored and is visible within the museum complex of Santa Maria della Scala). Among the buildings overlooking Piazza del Campo, you will see and should visit the Palazzo Comunale (or Palazzo Pubblico, which is the city's Town Hall) and the Torre del Mangia.
The imposing Palazzo Comunale, made in brick and marble, houses the Civic Museum with several masterpieces of Sienese artists, including the beautiful Majesty by Simone Martini and the cycle of frescoes called "Good and Bad Government" by Ambrogio Lorenzetti. Both are quite spectacular and should be seen in person.

2. Torre del Mangia
The Torre del Mangia, with its height of 87 meters, offers one of the most beautiful views of the city. The climb can be a bit tiring: there are over 400 steps, a bit steep and narrow, to climb but the 360° view that awaits you on the top of the tower is really spectacular and worth the "effort" you go through to reach the top. For those who want to visit both the Civic Museum and the Torre del Mangia, I recommend to buy the combined ticket: the frescoes of "Good and Bad" Government within the Civic Museum are extraordinary!

3. Piazza del Duomo
From here, our tour of Siena continues on to the precious Piazza del Duomo. While it is one stop, it is full of treasures that will take you the rest of the day to explore. Here you will enjoy some of the most magnificent treasures of Siena which I recommend you visit inside: the Cathedral, the Crypt and the Piccolomini Library. If you plan to visit these monuments, I suggest you to buy a cumulative ticket that allows you to visit the Cathedral, Crypt, Piccolomini Library, Baptistery and the Museum of the Opera del Duomo (where you can enjoy the view of the city from the “Facciatone”). Recently, a new itinerary inside the Cathedral has been opened, called "The Door of Heaven" that allows you to take a guided tour of the Cathedral from the top, enjoying truly extraordinary views.
-THE DUOMO OF SANTA MARIA ASSUNTA
The Duomo in Siena, or the Cathedral of Santa Maria Assunta, is one of the most outstanding examples of Romanesque-Gothic church in Italy. Imposing, almost dazzling for the extensive use of the white marble, the Duomo fascinates even from the outside. Entering, you will not be disappointed: the Cathedral is enriched with works signed by famous artists the likes of Donatello, Nicola Pisano, Michelangelo and Pinturicchio. The interior, like the exterior, is decorated with white and dark green (almost black) marble, a choice made to reflect the colors of the city of Siena. One of the most impressive works inside the Cathedral is without a doubt its pavement, consisting of 56 squares which represent scenes engraved and carved in marble. The most precious intarsios on the pavement are covered part of the year in order to protect them from wear. If you find yourself in Siena in the days of the Palio or between late August and October, however, you may have the chance to see the floor entirely revealed.
-THE PICCOLOMINI LIBRARY
The Piccolomini Library, dedicated to Pope Pius II, is striking for the richness of its frescoes painted by Pinturicchio and his pupils, including Raphael Sanzio in the early 1500s. Inside the Library, you can admire truly extraordinary frescoes on the walls, where you can see some scenes of the life of Pope Pius II, but also on the ceiling, shining for the abundant use of gold. The Piccolomini Library is a true gem that you really can’t miss once you're in Siena.
The library is INSIDE the DUOMO. Make sure you find it, as many won't find the small door on the left side of the church and MISS this treasure!
-THE CRYPT
The Crypt is located under the Cathedral. Here are many extraordinary frescoes of the Sienese school of the thirteenth century representing scenes of the Old and New Testament.

4. The Baptistery
The Baptistery is dedicated to San Giovanni and was built in 1300 when it was decided to enlarge the Duomo. The Baptistery, with entry from Piazza San Giovanni, is easily recognizable for its incomplete marble facade. The interior of the Baptistery is beautifully decorated with a cycle of frescoes by some Sienese artists of the Renaissance. The most precious masterpiece preserved inside the Baptistery is without a doubt the beautiful baptismal font created by some of the greatest sculptors of the Renaissance: Jacopo della Quercia, Lorenzo Ghiberti and Donatello.

5. The Opera del Duomo Museum
The Museo dell'Opera del Duomo is one of the oldest private museums in Italy and is located in the south side of the Cathedral, in an area that should have been an extension of the church on the basis of the project of the "New Cathedral", which was never completed. Here, you can admire the original statues from the facade of the Cathedral, including those made by Giovanni Pisano, the window of the apse by Duccio da Buoninsegna and one of the greatest masterpieces of the early Fourteenth century by Buoninsegna: the altarpiece of the Majesty. From the very top, you will get a great view of the cathedral and the rest of Siena!

6. Santa Maria della Scala
The complex of Santa Maria della Scala is one of the oldest hospitals in Europe, where pilgrims were welcomed (Siena is along the ancient Via Francigena pilgrimage route which connected Rome to central Europe) as well as the poor and abandoned children. The complex is located right in front of the Duomo, so is very easy to reach and visit.
Santa Maria della Scala still has some parts under restoration, but still remains open to the public, and houses a vast artistic heritage as well as temporary exhibitions. Arranged on four levels (the second is not yet accessible), it is a sort of "city within a city", so I suggest you consider if you have enough time to visit the entire complex or not before going in (as I have already said, you really should consider coming back to Siena for more than a day).



 

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