An unforgettable week in the Tuscan hills.

A complete itinerary that combines the beauty of some of the most important historical sites with the picture perfect landscapes of Tuscany. We start in the heart of the renowned Chianti wine region (between Siena and Florence) and then move towards the Val d’Orcia with it cypresses and olive trees. We will visit famous cities and discover small stone villages, and to stay charming and historic accommodation. This exciting tour is a harmonious fusion of nature and art.


Itinerary:

  • Day 1 – Florence, overnight in Florence.
  • Day 2 – Pisa and Lucca, Overnight in Florence.
  • Day 3 – Chianti Valley, overnight in Siena.
  • Day 4 – Siena, overnight in Siena.
  • Day 5   – San Gimignano and Volterra, overnight in Siena
  • Day 6 – The Val d’Orcia and Brunello, overnight in Siena or Florence.

Day 1 – Florence 

Arrival in Florence where we will welcome you to accompany you to your hotel accommodation. Leave your luggage in the room and let us guide you through the streets of one of the most fascinating cities in the world, rightly defined as an “open-air museum”, rich in art, history and beauties that can be seen and admired even just walking through the its neighborhoods, squares, bridges, hidden corners, the Lungarno. In Florence, art is everywhere let your gaze go. You won’t be able to see everything in one day, but with our guide we will make you want to come back soon.

Day 2 – A day in Pisa e Lucca.

Second day. Leaving Florence towards the sea, we reach Pisa in just under an hour. We leave early in the morning first destination Pisa, where the famous Piazza dei Miracoli awaits us, the Leaning Tower, with its 56 meters and 293 steps, the wonderful Baptistery, the imposing Romanesque Cathedral and the Camposanto, to represent the cycle of life, birth, life and death.

But Pisa is not only the Piazza dei Miracoli, the ancient Maritime Republic (the others were Venice, Genoa and Amalfi), the two beautiful riversides, meeting points with bars, restaurants, pubs and the medieval architecture of the houses that are mirrored in the Arno, with the Medici palace and the splendid church of San Matteo. A few steps from the church is the Borgo Stretto, a characteristic medieval street with ancient shops and shops, a street from the past.

A short distance from Piazza dei Cavalieri where the prestigious Normal University of Pisa is located and the Palazzo dell’orologio, whose tower was made famous by Dante Alighieri in the Divine Comedy with the story of Count Ugolino.

In the late morning visit to a dairy that has been producing fresh and aged cheeses for half a century and lunch with tasting of typical products of the Tuscan tradition.

After lunch, departure for Lucca. One of the most beautiful and loved cities in Tuscany, at the foot of the Apuan Alps and near the famous coast of Versilia. The city is enclosed within mighty Renaissance walls that today have become a beautiful park with tall trees and a continuous coming and going of people on foot or by bicycle enjoying the view of the city and the world outside, from above. Walking in the historic center of the city you have the feeling of being in another era, the mighty walls have prevented any change and the city of a hundred churches continues to enchant us, from the artisan shops, to the Duomo, to the Piazza dell’Anfiteatro, to which the steps have been removed to make way for the houses, but which keeps its charm intact. Return to Florence in the evening.

Option: For those who have already visited Pisa or Lucca, and would like to add a beautiful alternative, let yourself be transported to the hills of Vinci, Leonardo’s hometown, to visit his house museum and savor Tuscan flavors in the best farmhouses and wineries.

Day 3 – The Chianti Valley

Third day on the roads of Tuscany, today we will go to discover the countryside between Florence and Siena, the Chianti region, famous all over the world for the beauty of the views, the charm of the medieval villages, the wonderful gastronomy and for its red wine , certainly one of the best known in the world.

We leave Florence immediately after breakfast, walk along the Chiantigiana, one of the most beautiful roads in Italy, breathtaking views, rolling hills, vineyards as far as the eye can see, enchanting places, country roads where it is nice to get lost. Our first stop is in Greve in Chianti, the heart of the Chianti production, a village with a lively life that develops around the characteristic triangular square, whose portico creates a perfect setting for shops, artisan shops and restaurants, located under the arches. . In Greve we can visit the Wine Museum where over 200 wine labels from the region, many ancient agricultural equipment and more than 180 types of corkscrews are on display.

We continue towards Panzano in Chianti, the last village of the Florentine Chianti, whose center is divided in two, the upper, historical part with the medieval streets and walls surrounded by excellent restaurants and the lower part whose main square hosts outdoor restaurants and the typical atmosphere of the Tuscan villages.

Do not miss a visit to the famous Tuscan butchers, all but butchers, an institution that creates sympathy and appetite.

The next stop is Castellina in Chianti, which we can also call “in search of the perfect photo in Chianti”. The center is a beautiful quadrilateral, surrounded by imposing walls and even more impressive is the huge underground tunnel that runs under them, called the Via delle Volte and which houses shops, artisan shops and restaurants. Above, on the top of the Rocca tower, you can enjoy a spectacular view of the city and the countryside.

Lunch in a beautiful winery where a sommelier will guide us to discover the stages of production and bottling of some of the finest wines of the Chianti Valley.

We continue and our journey takes us to Rada in Chianti, Gaiole in Chianti, the smallest of the Chianti villages and finally to the Castello di Brolio where we can still taste wines and extra virgin olive oil from the Tuscan hills, one of the many wonderful castles that dot the Chiantigiana, where you can savor inimitable and unforgettable colors and flavors.

Day 4 – Ancien Village, San Gemignano, Volterra and Monteriggioni

Fourth Day. If in Florence you have taken a step back in the Renaissance, on this journey you will take a leap into the Middle Ages. First stop of our “excursion” the village of San Gemignano. The profile of its towers will appear as the natural continuation of the hill that hosts them. Located along the Via Francigena, it is one of the favorite sets for fantasy films, as well as being surrounded by a countryside rich and generous in agricultural products such as Vernaccia di San Gimignano or saffron, so precious that in the Middle Ages it was traded for gold, and also nowadays … … we enter from Porta San Giovanni and go up to Piazza della Cisterna, where you can taste “The best ice cream in the world” and then continue on to Piazza del Duomo where it is easy to come across a wedding or a movie scene, go down up to Porta San Matteo and then around the walls and savoring the wonderful panorama of the Val d’Elsa.

We leave for Volterra but only after stopping for lunch at a farmhouse with wine, cheese, salami and extra virgin olive oil tasting.

Volterra was the capital of the Etruscan world, but also the cradle of Roman, medieval and Renaissance civilization. A city that has always left its mark on Italian history over the last 3,000 years. From the spectacular Piazza dei Priori begins our visit to a village that is the capital of Alabaster, its hills offer various types but all require special skills for processing, skills handed down from generation to generation producing objects that are sometimes the fruit of many craftsmen. Narrow streets, wonderful artisan shops, charming restaurants, traditional street food and ancient stories of torture and vampires (many scenes from the Twilight movie were produced here), follow one another with breathtaking views that suddenly open onto the hills and vineyards.

In the late afternoon we resume the road to Siena where our day will end, not before having visited Monteriggioni, a beautiful medieval village, completely protected within powerful perimeter walls with its 14 towers that dominate the valley below where the vineyards reign. Once inside we find ourselves catapulted into another century, everything has remained intact, 570 meters of pure medieval magic of a fortress created by the Sienese on the Via Francigena, for the control of the passage of pilgrims who came from all over Europe to Rome and also for the control of the roads leading to Florence, Siena’s historical rival. After a walk along the walls, from which you can admire a splendid view of the countryside, we travel the last few kilometers that lead us to Siena. Arrival and overnight in Siena.

 Day 5  – Siena

Our fifth day is dedicated to Siena. The city center is located on various hills so expect some ups and downs, which we will face very slowly to savor the magic of the Sienese districts until we arrive in Piazza del Campo, famous for its particular shell shape and for the Palio di Siena, a horse race between the districts of the city that takes place twice every summer, on July 2nd and August 16th. We will offer you the opportunity to climb the Torre di Palazzo Comunale and the Torre del Mangia, to enjoy a spectacular view of the square and the city.

After a coffee and some photos we head towards the Duomo, a basilica built on three floors, following the profile of the hill, a precious example of Italian Romanesque-Gothic style, with its splendid marble mosaic flooring (unfortunately not always visible). On the lower floor, on the other side of the splendid main facade, we find the Baptistery, the Crypt and the Opera Museum.

We go down again towards the Piazza and the historic center, where our guide will introduce you to the secrets of the Sienese districts, small autonomous fiefs, each with a story to tell, a horse to love and a jockey to be king for a year. Siena is one of the richest Italian cities, rich in history and finance, here in 1472 the first banking institution in the world was born to develop the flourishing trade in wool, leather and agricultural products of this generous land. For the night, nothing better than a dinner in an ancient tavern tasting Sienese products and then a last walk in a beautifully lit Piazza del Campo.

Overnight in Siena, farmhouse or hotel.

Day 6 – The Val d’Orcia, scent of  Brunello.

Sixth and last Tuscan day, from Siena we reach Val D’Orcia, a valley so beautiful that it deserves the certification of World Heritage Site. Rolling hills, dotted with dark cypresses, red poppies and sunflowers make these landscapes a perfect setting for a day to carry in the heart and palate. The Val d’Orcia, from the medieval streets of Montepulciano to the smaller and more picturesque streets of Pienza, San Quirico D’Orcia and Montalcino.

In addition to its beauty, the area is known throughout the world for its DOC Brunello di Montalcino and Rosso di Montepulciano wines.

The first village we meet is that of Montalcino where grapes have been grown since the time of the Etruscans first and then Romans. The position allows an ideal solar exposure that makes the grapes ripen in a perfect way for a product particularly suitable to be subjected to long periods of aging with a decidedly superior flavor and taste, aroma and appearance. Walking up and down the steep streets is a pleasure for the taste, wine bars and small bars offer unmissable views and tastings and do not be surprised if here as in Siena, every now and then you encounter statues and effigies of the Roman she-wolf, symbol of the Sienese territory. Legend has it that Senio and Ascanio, sons of Remo, killed by his brother Romolo, fled and founded Sena (Siena) and Asciano.

We continue on provincial 14, savoring landscapes out of fairy tales, we meet the famous cypresses of San Quirico d’Orcia, the most photographed in Tuscany. San Quirico d’Orcia is a small wonderful village built on the Via Francigena, a path that in the Middle Ages moved hundreds of thousands of pilgrims and therefore potential customers. A little further on, on another peak Pienza, the city of sheep’s cheese, so famous and good that it is called Pecorino di Pienza. The Borgo is one of the Ideal Cities built in the Middle Ages to give dignity and quality to the life of citizens. Here it was Pope Pius II in the century Bartolomeo Piccolomini who hired the best architects to completely renovate the village. We will not miss the opportunity to visit Palazzo Piccolomini and taste the thousand shades of Pienza cheeses.

We arrived at lunch, our proposal takes you to a beautiful old farmhouse, transformed into a winery where you can taste the wines and products of the region.

In the afternoon, after a nice walk among the rows, Montepulciano, an incredibly beautiful village, awaits us as our last visit. Getting to the central square is a bit tiring but it’s worth it, the beauty of the streets, the buildings, the views that suddenly open up, the visit of the cellars and caves, the unique atmosphere of a magical village, the flavor of his Vino Nobile di Montepulciano. And if you come on the last Sunday of August, don’t miss the Bravio delle Botti, an uphill race with full wine barrels!

How to end such an intense day if not visiting a winery where they are grown among the oldest vineyards in Tuscany, watching Pienza and Montalcino light up the nearby hills at dusk, and taste wines and products, you don’t have to worry, this is one of the advantages of being accompanied by those who know and take care of you.

Return to Siena or Florence, where our itinerary ends.

Option to continue following our itinerary to discover the Umbrian villages up to Rome.


  • What’s included: 
  • 6 overnight in hotel or farmhouse.
  • All taxes
  • All transfers
  • Tour guide for whole the inteire period
  • Local guide in Florence
  • A wine tasting in Chianti Valley and in Val D’Orcia
  • Entrance tickets when required

  • What’s not included: 
  • Personal expenses.
  • Lunch and dinner
  • Anything not expressly included

Pernottamenti in Hotel, B&B e/o Agriturismo