8-Day Tuscany Villa Itinerary: Explore Tuscany's Best in a Week

When you are set up and relaxed, what about starting your Tuscany exploration by exploring San Gimignano? It's just 18 Km from your villa.

A visit to San Gimignano is a complete immersion into the 1300s borgo ambience; in fact, the city, still mostly intact today, is one of the best representatives – in terms of planning and organization – of the European commune (essentially, the urban version of the feudal system) from the Middle Ages.

The overriding characteristic of San Gimignano – that just about every visitor will notice from a distance – are its spectacular and unmistakable towers that watch over the scene. And each one has its own history.

The town experienced a period of economic wealth and artistic flourish, above all in the mid-1300s, thanks to the merchants and pilgrims traveling along the Via Francigena; the route passed through San Gimignano, dividing it into two.
It was also during this time that the town’s foremost families challenged each other in building the highest tower, attempts to exhibit who held the most power.
Around the year 1300, 70 towers symbolized the 70 wealthy families inhabiting this territory. Today, only 13 remain standing.

It was also in the same century that San Gimignano underwant a process of architectonic renovation, that comprised an expansion of the walls, the construction of numerous new palazzi, churches and convents – in the environs of Piazza della Cisterna and Piazza del Duomo - and their adornment with illustrious works of art. 

It is the Tuscany that tourists love most, set amidst fields of golden grain, vineyards and ancient borgoes; it is the Tuscany of Chianti and the Val D'Orcia, of beloved culinary traditions and singular tastes.

Siena is with Florence one of the most fascinating Tuscany city, with century of history, battles and art. This walking tour will take you through the most beautiful corners, square and streets of the city.

We will start with a nice stroll from Saint Domenic Church and we will learn about her most famous lady Saint Catherine. After We will cover the footsteps of the many "pilgrims" that crossed this city during the middle ages walking along the main street and reaching the Cathedral, one of the most beautiful Gothic church of Italy. Here Michelangelo, Donatello, Bernini and so many others enrich the church with fantastic works of art.

Walking tour finishing point will be in heart of the city, the Campo Square. This is is one of the most beautiful square in the world where twice a year there is the famous horse race competition "the Palio". Lets learn more about this fantastic tradition so old and still so alive!

After the tour is finished, keep on exploring th enarrow streets on your own and don't miss to purchase the typical pastries (Ricciarelli, Panforte and Panpepato) at the famous Nannini café, close to the Campo square.

The lovely and off the beaten path Monteriggioni hamlet stands on top of a low hill whose slopes are dotted with olive trees and vines, a few km from Siena.

The castle was founded in the second decade of the 13th century by the Republic of Siena. Its main aim was to create a defensive outpost against its rival, Florence. For centuries the site carried out this function for which it was created, resisting countless sieges and attacks, one after the other. Its military function became less important in the second half of the 16th century, when the whole state of Siena, which the borgo was part of, was annexed to the state of Florence. 

Today, Monteriggioni is a perfectly preserved fortified village. You can walk on the city walls to admire the Tuscan countryside, and eat in one of the local restaurants.

The area around Monteriggioni and San Gimignano is called Val d'Elsa. Here you will find many off the beaten path lovely hamlets, where you will be mostly on your own (because mass tourists only go to San Gimignano!).

If you have time we suggest you visit Colle Val D'Elsa and Casole d'Elsa, two delightful hidden jewels.

Today you will learn to cook a traditional Tuscan meal during a 4-hour cooking class accompanied by an experienced cook who will guide you and give you great tips. At the end of the class, you will savor the various dishes you've prepared.

Meet the cook and the rest of the group in the morning on via Ricasoli and head to the Mercato Centrale Firenze.

Step inside the bustling central market and wander past the numerous colorful stalls accompanied by the professional cook in search of the right fresh produce and ingredients to make the best dishes. It’s a great opportunity to practice your Italian and meet the vendors selling their home-produced vegetables, fruit, cheese and wine. 

With your basket full of foods, you’ll head to a fully equipped kitchen in a striking setting, where you’ll prepare your meal. The authentic 4-course lunch usually consists of bruschetta, a fresh pasta dish made from scratch, a main course and dessert.

When you’ve finished, sample your cooking accompanied by a refreshing Chianti wine. The cook will give useful advice and ideas to continue mastering your cooking skills at home.

The cooking class will finish at approximately 3 pm.

1. Start at Florence Cathedral (Duomo) Spend 30 minutes here exploring the outside and inside. The beautiful Gothic style cathedral, formally known as Cattedrale di Santa Maria del Fiore, is the most iconic landmark of Florence. Don't forget to admire Brunelleschi's dome and Giotto's bell tower.

   Walking time to next location: 5 minutes

2. Piazza della Repubblica This is one of the main squares in Florence and was the forum in the Roman city. Today, it is surrounded by cafes and you can take a few minutes to have a quick espresso or just enjoy the ambiance.

   Walking time to next location: 5 minutes

3. Ponte Vecchio It's a lovely 10-minute stroll from Piazza della Repubblica to Ponte Vecchio, the oldest bridge in Florence. The bridge, filled with jewelry shops, has an incredible history and it's a nice place for a photo.

   Walking time to next location: 8 minutes

4. Palazzo Vecchio and Piazza della Signoria This is the heart of Florence. The piazza is an open-air sculpture exhibit with replicas of famous statues including Michelangelo's David. Spend around 30 minutes here.

   Walking time to next location: 5 minutes

5. Uffizi Gallery You will need to pre-book tickets to avoid the lines. As one of the world's most famous art museums, it holds countless masterpieces. It's impossible to see everything in one visit, but even a short hour here will be memorable.

   Walking time to next location: 15 minutes
   

6. Basilica of Santa Croce A 15-minute walk from Uffizi Gallery, you'll find Basilica of Santa Croce, the burial place of famous Italians like Michelangelo, Rossini, and Machiavelli. Spend about 30 minutes here.

   Walking time to next location: 10 minutes

Today you will discover one of the most famous Italian wines: the Brunello di Montalcino.

You will drive to the renown historical Fanti winery, where you will experience a guided tours of the cellar followed by a tasting of the estate wines and extra virgin olive oil. 

The wine cellar is located in the valley of Castelnuovo dell'Abate (which lies in the south of Montalcino) in front of the medieval Abbey of Saint Antimo. Winery visits are available upon reservation in English and French.

Bagno Vignoni is very unique: nowhere else in Italy will you find its main central square has a pool filled with hot springs water. 49 meters long and 29 meters wide, the Renaissance-era piazza is built directly over the original source of hot springs as enjoyed by the Romans.

Since the 9th century, the springs here and in Bagni San Filippo, located a bit further south at the foot of the Monte Amiata, have been mentioned in old travel journals of abbots and others making their pilgrimage down to Rome (and many on to Jerusalem). 

The hot springs in Bagno Vignoni have always allowed water to flow even during the warm summer months, thus several water mills were constructed along the Orcia river over the centuries. These ancient mills, along with a complex system of water canals and gorges today constitute the Parco dei Mulini, or Park of the Mills, created in the 1990s.

Don't forget to bring along a swim suit and towel when visiting to enjoy the hot springs. Of course, you can take a break for a whole day and enjoy the many spas.

This is also a good place to have lunch, we suggest Osteria del Leone for great local specialties.

This is probably one of the most photographed spots n Tuscany. This cypress lined lovely road is just a few km before Pienza.

The medieval Montichiello Hamlet deserves a visit as well.

Pienza, a Unesco world heritage site, overlooks the Val D’Orcia and is the first example of Renaissance “ideal city”, i.e. a town built according to architectural criteria of antique classics that would impact directly on the human soul, stimulating spiritual well being.

It’s old walls and buildings are full of atmosphere and are a fantastic romantic destination.

The wonderful walk along the ancient walks has been named “Via dell’Amore” (no need to translate…), and offers fantastic views over the Val d’Orcia.

Pisa is a world known town north of Florence, home of the "leaning tower", one of Italy icons.

The first sight not to be missed is Piazza dei Miracoli (“Square of Miracles”), the huge square hosting the tower, the Cathedral, the Baptistery and the monumental graveyard. The square is surrounded by a beautiful green lawn, and the contrast between the green grass and the dazzling white monuments has always struck me.

Santa Maria Assunta, the awsome Cathedral, dominates the square with its beautiful Romanesque architecture. It hosts many important works of art, such as the great mosaic of St. John the Evangelist in the apse (1302) by Cimabue, or the Pulpit, a masterpiece by Giovanni Pisano.

If you plan to climb on top of Pisa tower you should reserve well in advance your ticket (of course we can help you).

Even though neglected by mass tourism, Lucca is an unmissable destination in Tuscany. Despite it is relatively small site, its city center hosts amazing monuments and sights, dating from Roman age to renaissance. 

But what makes Lucca really unique are its Renaissance-era city walls that have remained intact while so many other Tuscan towns saw theirs destroyed in past centuries.

On top of the city walls (built between the first half of the sixteenth and mid seventeenth century the Walls of Lucca are intact until today), here are the things you shouldn't miss in your tour:

• San Michele in foro: the church is built in the large square that was originally the Roman Forum in the center of Lucca. It’s a beatiful square, lined with medieval buildings housing cafes, shops, and homes.
• Piazza anfiteatro: it's one of Lucca landmarks, nearly as famous as its walls. It’s an oval shaped piazza, that was once a Roman amphitheater. Buildings and houses were built around the arena during the middle ages, giving the square its oval shape.
• Basilica di San Frediano: its facade is decorated with a stunning 13th century Byzantine-style mosaic. Made mostly with gold leaf mosaic that glow beautifully in the sunlight, there’s also a little color to make the apostles and Christ stand out. T
• Duomo di San Martino: Lucca’s cathedral, dedicated to San Martino or Saint Martin, sits on Piazza San Martino surrounded by impressive medieval buildings. Originally build in the 12th to 13th centuries, it’s Romanesque in style and has an intricately decorated marble facade. The interior is Gothic and holds good artworks, including the Volto Santo and the 15th century touching tomb Ilaria del Carretto, a masterpiece by Jacopo della Quercia.

Your guided tour will include the highlights of that adorable town: the Renaissance walls, the Amphitheater square, Saint Michael square, the more beautiful and narrow medieval streets until Guinigi tower, cathedral square and of course San Frediano church. The tour will be 50% by bike and 50% by walking, for 2 hours in total.

Your Chianti itinerary begins along the "strada del vino" ("wine road", 222 ss route), just south of Florence. 

First stop stop on your tour is the Castello di Verrazzano. The castle of Verrazzano is located on a hilltop in the Chianti Classico region, overlooking beautiful countryside. You will participate to a guided tour in small accompanied groups to the Renaissance gardens of the Castle and to the historic aging cellars built directly into the hill below it. 

Then you will taste the estate wines: Verrazzano IGT Toscana, Verrazzano Chianti Classico DOCG, Verrazzano Chianti Classico Riserva DOCG, Tasting of organic Extra Virgin Olive Oil "Castello di Verrazzano", Tasting of "Balsamico Verrazzano ”on pecorino (sheep cheese). 

The next stop is Greve in Chianti, which is considered by many to be the gateway to Chianti and is famous for its peculiarly shaped piazza or square, which has been the market place for the castles and fortified villages of the surrounding area since the Middle Ages. The square is triangular in shape and has large porticoes, dotted with beautiful shops and delicious restaurants. 

Have a look to the amazing Enoteca Falorni, one of the largest of Tuscany. Here you can taste any Tuscan wine (not only Chianti), including Brunello and "Supertuscans" 

your driver will get you to Castello di Vicchiomaggio, where you will have lunch and, of course, taste the estate wines. Lunch "à la carte". 

After lunch, visit of Castellina in Chianti. Located along the Chiantigiana road that connects Florence to Siena, it is one of the most important destinations in Chianti. Once a fortified village, you will discover along the ancient walls an impressive underground tunnel used by the guards, the Via delle Volte. You will also enjoy the impressive fortress that gives the village its name (Castellina derives from the word "castello", Italian for castle). 

We can organise a private tour if you don't want to bother about driving after drinking,

Today you will discover one of the most famous Italian wines: the Brunello di Montalcino.

You will drive to the renown historical Fanti winery, where you will experience a guided tours of the cellar followed by a tasting of the estate wines and extra virgin olive oil. 

The wine cellar is located in the valley of Castelnuovo dell'Abate (which lies in the south of Montalcino) in front of the medieval Abbey of Saint Antimo. Winery visits are available upon reservation in English and French.

Bagno Vignoni is very unique: nowhere else in Italy will you find its main central square has a pool filled with hot springs water. 49 meters long and 29 meters wide, the Renaissance-era piazza is built directly over the original source of hot springs as enjoyed by the Romans.

Since the 9th century, the springs here and in Bagni San Filippo, located a bit further south at the foot of the Monte Amiata, have been mentioned in old travel journals of abbots and others making their pilgrimage down to Rome (and many on to Jerusalem). 

The hot springs in Bagno Vignoni have always allowed water to flow even during the warm summer months, thus several water mills were constructed along the Orcia river over the centuries. These ancient mills, along with a complex system of water canals and gorges today constitute the Parco dei Mulini, or Park of the Mills, created in the 1990s.

Don't forget to bring along a swim suit and towel when visiting to enjoy the hot springs. Of course, you can take a break for a whole day and enjoy the many spas.

This is also a good place to have lunch, we suggest Osteria del Leone for great local specialties.

This is probably one of the most photographed spots n Tuscany. This cypress lined lovely road is just a few km before Pienza.

The medieval Montichiello Hamlet deserves a visit as well.

Pienza, a Unesco world heritage site, overlooks the Val D’Orcia and is the first example of Renaissance “ideal city”, i.e. a town built according to architectural criteria of antique classics that would impact directly on the human soul, stimulating spiritual well being.

It’s old walls and buildings are full of atmosphere and are a fantastic romantic destination.

The wonderful walk along the ancient walks has been named “Via dell’Amore” (no need to translate…), and offers fantastic views over the Val d’Orcia.

No particular activity scheduled for today, to give you the freedom of deciding what to do. 

If you still want to visit, the obvious choice is Volterra, a spectacular Etruscan town just 40' drive from San Gimignano.

Today, Volterra is particularly renowned for its peculiar urban layout that reminds us of its Etruscan origins: people can still visit part of the majestic protective walls built during the 5th to 4th centuries BC - including the well-preserved Porta dell'Arco and Porta Diana, two gates for entering the city - as well as the Acropolis that houses several buildings and the foundations of two ancient temples. There are many Roman remains to visit as well, like the Roman Theater, dating back to the end of the first century AC, built in a natural amphiteatheater shape area.

Alternatively, you can spend the whole day in Florence, browsing the old streets and visiting some of its fantastic museums.

Of course, you can just stay at your villa swimming pool and enjoy the scenery and the "dolce vita"!

Depending on your flight schedule, enjoy a comfortable breakfast and then drive to the airport, where you will return your car and catch your flight back home