From Chianti to the Val d'Orcia, hidden destinations for your holiday

Discovering the treasures of Tuscany

Tuscany is a wonderful region and certainly everyone agrees, for those who love mountains, sea, countryside and art cities, this is a region full of surprises that very often visitors ignore.


A note from Lisa

The itinerary that we would like to suggest to you, will not include neither Florence or Siena, nor Pisa, etc...

the classic destinations that everyone knows and undoubtedly is a must to visit, but many tourists do not know that there is much more when they visit this region! What you will find in this section, is something "unspoilt", which is easily accessible from Podere Casanova.

Happy Holidays to all from Lisa and the whole family of Podere Casanova!

Good Morning!

Our apartments are equipped with everything you need to prepare a good breakfast, from coffee maker, toaster, kettle, etc., but if you would like to taste a good Italian breakfast (cappuccino, brioche etc ...) we recommend:

  • BAR SILVANO: just 500 mt from Podere Casanova, ideal for children, couples and families. It has a large car park surrounded by a forest, which is very clean and well kept, where you can also take lovely walks. In addition, Bar Silvano has a large outdoor area with swings/slides, video games, football, ping pong, tables and chairs are also available both indoors and outdoors, where you can enjoy your breakfast in tranquillity and framed by the singing of the birds. Inside Bar Silvano there is also a minimarket where you can purchase fresh home bread, fruit, pasta etc ... open every day and Sundays. On Saturdays and Sundays they offer a pizza service with reasonable prices.
  • PASTICCERIA PAOLINI: is located 7 Km from Podere Casanova, it overlooks the main square of Montespertoli and opened in 1982. It is a patisserie with an ancient taste, where everything must be calmly savoured. Here, you can enjoy the aroma of the coffee, the richness of a thick and frothy cappuccino, the goodness of the patisserie, where pastries, cakes and mignon, chocolate, candy sweets, all handcrafted and gift wrapped, the best chocolate brands beautifully displayed.
  • PASTICCERIA LA FIORENTINA: is 7 km from Podere Casanova, it was renovated in 2007 and is situated in the most ancient street of Montespertoli (via Roma). It has a modern decor and mostly frequented by young people, which makes it a perfect meeting point. Here, you can enjoy a good coffee, cappuccino etc. The perfume of baked pastries and cakes makes this patisserie a fashionable place for those who love breakfast. It is frequented mostly by young people thanks to its modern decor. In the summertime, you can sit and enjoy your breakfast on the comfortable rocking chairs.

First day - A day in Montelupo and Vinci

Departure is in the morning from Podere Casanova. After an abundant breakfast, ideal for those who enjoy long walks, let’s find out what to see in one day...

The morning, Montelupo

Depart from Bottinaccio (Podere Casanova), 6 km away from Montelupo. Arrive in Montelupo (small and charming village famous for ceramic and terracotta). Montelupo is absolutely worth visiting, especially for those who love ceramics and terracotta. In the historical centre, just refurbished a few years ago, you can find many shops, where you can admire and purchase hand painted ceramics and terracotta of an incredible beauty.

These products are not very cheap to purchase, because they require a very long and difficult working process.

To be able to get cheaper prices, you must purchase the products within the factories, where in addition of their direct sales, you can see the whole working process.

On a customer's request, Podere Casanova, with no additional cost and no obligation to purchase, will lead you to discover the ceramics and terracotta and if you are lucky, you or your children can make your own ceramic jar to take home.

  • Le Ceramiche: CERAMICA LEONA
  • Terracotta: DI.MA. Ceramiche e Terrecotte - Via Virginio 196, Montespertoli Firenze

It is important to understand how the ceramic is the beating heart of Montelupo in fact, twenty years ago; the School of Ceramics was opened with students coming from all over the world.

Events in Montelupo

  • The Festival of Ceramics. Every year, the third week of June, for a week, Montelupo becomes the "town of ceramics”. The city centre is transformed into one big atelier, where, next to the shop windows of the manufacturers of ceramics, the historical, monograph or thematic exhibitions take place, devoted to Italian and European ceramics. In the evening, after dinner in one of many typical restaurants, or in those organized by local volunteer groups in the most picturesque locations (the fortress, the ancient manufacturing of ceramic, ...) you will then attend demonstrations by the ceramic maker, painters or glass blowers, music show, and also a stroll among the colourful stalls of the marketplace, which ends at the feet of the medieval walls.
  • The Festival of Terracotta. Nel mese di Maggio, per un fine settimana, nel Borgo di Samminiatello (poco distante dal centro storico) si svolge la tradizionale festa dei terracottai, organizzata dall'Unione Fornaci della Terracotta. Al centro l'esibizione dei maestri della terracotta, impegnati nella creazione dei mastodontici orci e conche; intorno stand gastronomici e mostre collaterali.
  • La Torre del Vetro. The working process of glass is the heart of this festival, which is also dedicated to a weekend in July, in the village of Torre. On this occasion you can admire the masters of glassmakers at work (blowers, engravers and decorators), who are always active and working for the companies of this area, as well as the remaining women who make the straw flasks for the wine bottles, which (now only a hobby) is preserved as an ancient technique.


After visiting Montelupo, lunch break. If you were in the town centre, we advice you to eat at:

  • Antica Osteria del Sole - Via XX Settembre 23, Montelupo Fiorentino - 0571 51130 - Here you can eat pizza to Florentine steak.
  • Antica Trattoria del Turbone - Via Turbone 37, Turbone - 0571 542035 - Outside the historical centre, another restaurant, its specialties are: Fried rabbit, codfish and Florentine steak. Here you can eat typical Tuscan food and good pizza on the terrace.

The afternoon, Vinci

It is immersed among vineyards and olive groves, which give a good-quality wine and olive oil. Vinci is situated on the slopes of Montalbano, between the provinces of Florence and Pistoia.

It was born as a possession of the Counts Guidi in the first half of the XII century; the castle of Vinci came under the governance of Florence between 1254 and 1273 and then turned into a Municipality.

It is here in Vinci, exactly in Anchiano, where Leonardo was born, on the 15th April 1452 and where he spent the years of his childhood: his universal recognition as a genius, are tied to the most evocative locations of the city.

Underneath Via Montalbano, you will find the Museo Ideale Leonardo Da Vinci, a private collection that gathers documents and reconstructions on Leonardo.

In the central square of Piazza della Liberta’ is placed the bronze equestrian monument (1997) by the sculptor Nina Akamu, inspired by the numerous drawings of horses by Leonardo. At the crossroad between the road to Empoli and Cerreto Guidi, the Sanctuary of the Santissima Annunziata retains the valuable painting with the Annunciation of the Pistoiese Monk Paolino, dating back around 1525.

From the centre of Vinci, passing through the olive groves, the ancient trail called "green road" or scenic road; you will reach Anchiano, the birthplace of Leonardo da Vinci, a typical rural dwelling of XIV century that belonged to the Counts of Tuscany, which has been certified that Leonardo was born on 15th April 1452.

In the surrounds of Vinci, we point out the Romanesque churches of San Giovanni Battista in Sant'Ansano in Greti, San Pietro in Sant’Amato situated in a beautiful panoramic position, and the church of Santa Maria in Faltognano, preceded by a large lush green terrace, which is overshadowed by an old majestic Holm oak tree.

At night Vinci is lit up by romantic lighting, with its breathtaking landscape, suffused lights that illuminates the small village, giving the impression that time has stopped, you will enjoy a dreamy evening.

Dinner in Vinci

  • RISTORANTE LA TORRETTA DA PIPPO (GREAT!!) - Via della Torre. Vinci

Wine Shops

  • Enoteca Antica Cantina Di Bacco - Piazza Leonardo Da Vinci 3, Vinci - 0571 568041
  • Enoteca Borgo Allegro - Via R.Fucini 12, Vinci - 0571 567866 - closed on Tuesday

Wine Tasting

  • La Querciola (ottimo) - località Querciola, 43 - 0571 567777 - closed on Monday

The first day in Tuscany is concluded returning to the Podere Casanova, which is 20 Km from Vinci.

Second day - A day in San Miniato, Certaldo and Monteriggioni

Departure from Podere Casanova in the direction of San Miniato Alto.

The morning, San Miniato Alto

On the map, the "Samminiatesi hills" link the Florentine area of Montespertoli and San Casciano, the Valdelsa of San Gimignano and the inland of Pisa countryside until Etruscan Volterra, on clear days; you will see the monuments from the hill of Rocca. The town consists of buildings of various ages, arranged mostly along the main street. The 1200 century tower is attractive (rebuilt after the Second World War) that evokes Federico II and Pier delle Vigne: According to some sources, he fell into a disgrace, he might have been locked in the tower and from there he committed suicide. (It was also claimed by Dante Alighieri in presumption of his Divine Comedy). San Miniato is renowned worldwide for the truffle, it is one of the most extensive and fruitful areas in Europe for truffles. If in the months of October and March you are staying at Podere Casanova, these festivals must not be missed.


  • Festa del Tartufo e del Fungo di Balconevisi - Balconevisi, San Miniato - Third Sunday of October
  • Festa del Tartufo di Corazzano - Corazzano, San Miniato - First Sunday of October
  • Festa del Tartufo Marzuolo - Cigoli, San Miniato - March

Typical products of San Miniato

  • fresh truffles
  • white truffle
  • black truffle
  • chese with truffles

After visiting San Miniato Alto, I suggest to return towards Montespertoli for lunch.

Lunch in Montespertoli

In Montespertoli you can choose to eat in a restaurant or more typically a quick sandwich. Podere Casanova recommends:

Paninoteche a Montespertoli

  • "Bar Silvano" - via Botinaccio Loc Botinaccio Montespertoli - also open on Sundays
  • Paninoteca "Dalla Giovanna" - via taddeini Taddeino Montespertoli - also open on Sundays
  • Paninoteca "la Panetteria - via Taddeini Taddeino - also open on Sundays

Restaurants in Montespertoli, open for lunch and dinner

  • Ristorante Pizzeria "il Battibecco" via Taddeini Taddeino
  • Ristorante "La Terrazza" (typical Tuscan specialities)

Afternoon, Certaldo Alto and Monteriggioni

In the direction of Certaldo Alto.

Certaldo Alto, is an ancient village of incredible beauty, must not to be missed. Valdelsa is one of the most scenic landscapes of Tuscany, for the beauty of the hills edged by cypress trees, castles and towers. Certaldo draws the unmistakable profile of its perched, red cotto village.

In the medieval village, in mid-July, a wonderful international exhibition of the street theatre "MERCANTIA" takes place.

This is another interesting festival that is always held in Certaldo Alto "BOCCACCESCA", this event is perfect for those who love the Tuscan cuisine and it is held in the first two weekends of October. A few km from Certaldo (approx.40 Km) you can reach Siena, we recommend to those who have already had the privilege to see Siena, to visit the CASTLE MONTERIGGIONI, which is absolutely wonderful.

To view the Monteriggioni Castle from afar, you will experience being back in ancient times, giving you the impression that time has stopped, outside and inside the circle of its walls. The people now obviously have changed, but those who chose to live in the castle, have kept the slow and rich life of man’s dimension and nature, with the values of the farming culture and constant contact with history. For the travellers, the image of the castle was and still is very impressive, in which it appears bold and dominant on top of the hill... like a sentinel defending the ancient Republic of Siena.

Dinner in Monteriggioni

If you want to continue to enjoy the medieval atmosphere of this place, you can make a pit stop at these restaurants; "Il Piccolo Castello" or "Il Pozzo", which are located within the walls of the castle, here you can taste the real traditional Siena cuisine.

  • Ristorante Il Piccolo Castello - Via I° Maggio 1, Monteriggioni Castello - Siena - 0577 314370
  • Ristorante Il Pozzo - P.zza Roma 20, Monteriggioni - Siena - 0577 314370 - Closed on Sunday evening and Monday

Monteriggioni like Certaldo is famous for a beautiful medieval festival that takes place in July: The medieval festival "Monteriggioni di torri si corona" is held every year during the second half of July. It is a reminiscent celebration of the history and cultural traditions of that period of Monteriggioni, now passed. This festival is amongst the three most important medieval festivals in Italy. There are people coming from all over Italy to admire it. It seems like stepping back in time in the mid-1200, when Monteriggioni was not just a castle with a garrison; it was also a village where everyday life occurred. For this event, all the people are dressed in ancient clothes and perform their character: the farmer, the merchant, the soldier, the crossbowman, the monk ... so as to make life more real in the village.

In addition to this wonderful festival, there is also another held in Monteriggioni:

Oltre a questa meravigliosa festa, sempre a Monteriggioni:

  • Feast of Autumn - It is celebrated on Saturday and Sunday of the first week of October in honour of the Madonna Del Rosario, patron of Monteriggioni, it is a party where the sacred and profane blend well. Outside the church, in the opposite square, there are stalls where the local people are dressed with “vintage” clothes serving sandwiches with typical Tuscan salami, roast pork and local delicacies. They also serve autumn products such as roast “chestnuts" and others autumn specialities.
  • Christmas torchlight procession on the Via Francigena - On 24th December, at 21.30 in Piazza del Castello of Monteriggioni, where torches will be given and at 21.45 the marching starts all in a row, in order to create a long snake of lights, then out through the doors of the Castle, continuing along the slopes of the hill on Via Cassia, to continue the journey to Via Francigena until Badia Isola, where the holy midnight mass is held in the abbey. After the mass is held, a buffet is offered by the voluntary associations of the town, a toast and exchange of greetings. The torchlight procession is very suggestive; it attracts people from all over Tuscany, and for the event the walls of the castle are illuminated by small oil torches.

Third day - A day in Cortona

Departure from Podere Casanova, in the direction Cortona

Cortona is 1.40 hours away from Podere Casanova.

Cortona is a wonderful city; it is about 80 km from Florence and is considered as one of the richest historic cities and works of art. Cortona has a history of over 2000 years that make this one of the most characteristic and fascinating cities of central Italy and an ideal location to understand and comprehend our Italic origins.

Visiting Cortona is not just to go to churches or museums, but also walking through the steep streets breathing the perfume of burning log wood fireplaces, still today used both for heating homes and cooking.

What to see

  • Fortress of the Gyrfalcon of Cortona. The Fortress of the Gyrfalcon of Cortona is one of the jewels of medieval Cortona
  • Cathedral
  • Chiesa di Sant'Agostino between Via Guelfa and Via Ghibellina close to the church of San Benedetto.
  • For those who park their cars below the walls can walk up directly through Porta Sant'Agostino.
  • Piazza della Repubblica. Piazza della Repubblica is one of the biggest squares of Cortona. It overlooks the Palazzo Comunale, almost like a balcony, the small square of Loggetta with Palazzo Passerini.

Events in Cortona

  • "GIOSTRA DELL'ARCHIDADO" in April, May and June

Where to eat

  • Ristorante La Bucaccia - Via Ghibellina 17, Cortona - 0575 606039
  • Ristorante Bistrot Preludio - Via Guelfa 11, Cortona - 0575 630104

Fourth day - A day in Greve in Chianti

Departure is from Podere Casanova in the direction of Greve, in Chianti, 1 hour away. Greve in Chianti, èin my opinion, is one of the most beautiful towns of the Chianti area: the main square, today dedicated to Giacomo Matteotti, with its characteristic funnel shape, has been called for centuries "Mercatale in Greve", in ancient times and even today it is the beating heart of the city, vibrant, surrounded by arcades, and organized markets and festivals are held during the year. Greve is also surrounded by charming villages, such as Montefioralle with its houses made of stones and cobbled alleys or Panzano, which overlooks the beautiful Romanesque church of San Leolino with a portico of XV century that has five arches. Inside are kept valuable works of art.

In addition to the beautiful villages near Greve, there are many castles now turned into beautiful villas and farms.

What to see in Greve

  • Fortified medieval village of Montefioralle. The village of Montefioralle is worthy to visit for its "castle", the pleasant climate and beautiful landscape. It is easy to reach from Greve or by foot after walking uphill for 20 minutes or quicker by car. From Montefioralle there is an attractive walk through secondary roads towards Panzano. Not to be missed in March, the Sunday after St. Joseph’s day, they prepare frittelle in a big huge pan, which are sweet rice cakes fried in oil.
  • Pieve di San Cresci. The parish church of San Cresci, dating back to the 10th century, is one of the most important Roman constructions in the region of Chianti.

Where to eat

  • Ristorante "Taverna del Guerrino" - Castello di Montefioralle - Famiglia Niccolai - 055 85 31 - In the summertime you can dine outside on the terrace. Their menu is very limited, but is made with love and simplicity, typical of housewives in this area and includes: fettunta (Tuscan version of Bruschetta), croutons, Tuscan salami, wild boar sausage, bread made with tomato, ribollita (dish based of bread, cabbage and beans), pasta with wild boar and continues with grilled meat, including the rosticcianne and Chianina beef steak, to finish with home made cakes accompanied by vinsanto and of course with the local wine from the area.
  • Ristorante Locanda "Il Borgo Antico" - Dimezzano - Frazione Lucolena, Greve in Chianti - 055 851024

Fifth day - A day between Castellina, Radda and Gaiole

Departure from Podere Casanova, in the direction of Castellina in Chianti, Radda in Chianti and Gaiole in Chianti.

These three villages are located just 1 hour away from Podere Casanova.

These are three villages near each other; they are of a unique beauty. The journey to get there, is wonderful, the road of Chianti offers breathtaking views that you will always remember.

Castellina in Chianti

To reach this small village you must follow the signs to Poggibonsi and take the SS429, where you will enjoy the view of our wonderful Tuscan hills. Castellina in Chianti is situated in a beautiful hilly position; its territory is part of the most important of Chianti Classico. Its origins date back the Etruscan and Roman times, the noble fief of Trebbio (XII century), then became an important Florentine military garrison. It was the chief league town of Chianti, with Radda and Gaiole in XIII century. Not far from the town of Castellina there is a great Etruscan tomb dating back to the sixth century BC, this is the most interesting local archaeological discovery.

Radda in Chianti

Another small village of a unique beauty, set on a hillock, today it is mainly an agricultural centre, Radda, today the ruins of the walls and towers of the ancient fortified medieval town are still preserved, and the town planning structure is in an extended elliptical shape. In the centre of the village, is the remarkable Palazzo del Podesta, adorned with the coat of arms on the front. Not far from Radda, taking one of the two roads that lead to Panzano, you will reach the village of Volpaia; the village was built as a fortified village of medieval origin. For its sentry position on the Pesa valley, the castle was certainly an important defence. The fortified complex has now lost part of its walls, but some parts are still preserved, such as the bridge house, placed at the centre of the little square and above all, several medieval houses.

Gaiole in Chianti

A Winery centre surrounded by green hills. It is not far from the centre of Gaiole, immersed amongst the woods and vineyards, there are two medieval fortified complexes: the parish church of Santa Maria a Spaltenna (first half of the XII century) and the village of Vertine, enclosed within an oval shaped walled perimeter.

Sixth day - A day in Pienza

Departure from Podere Casanova in the direction of Pienza.

Pienza is for those who love cheese, it is 2 hours away from Podere Casanova.

Pienza is a small jewel of the Renaissance, in the heart of Tuscany. Pienza is still a city full of charm. Walking amongst the narrow streets it is very emotional. Along the streets of the village you can discover suggestive corners and buildings of various interests. Pienza is one of five villages that overlook Val D'Orcia:

  • Castiglione d'Orcia
  • Montalcino
  • Pienza
  • Radicofani
  • San Quirico d'Orcia

Amongst these five wonderful villages, rich of history, we recommend that you spend a day just in the village of Pienza. There are many things why you should visit Pienza, for example:

The local gastronomy

Cheese is the typical product of Pienza, but it is better to say Pecorino. Strolling along the streets, you will come into a street and recognize it immediately because of the odour of cheese and cold cuts that will lead you to “this gourmet paradise corner". Along the way you will be fascinated by inviting and delightful shop windows, which are not normally gourmet shops but "stone lounges" of an incredible beauty, and in many of them food tasting is possible.

The romantic side of Pienza

Besides the culinary tradition, Pienza is a village that can give you moments of true romance, thanks in particular to some of the names that the streets have, such as: Via del Casello, very romantic for its narrow and overshadowed streets, such as Via dell 'Amore, Via della Fortuna, Via del Bacio and Via Buia.

The Architecture

For those who love architecture, Pienza can offer many ideas. In ancient times Pienza was a small fortified village, known as Corsignano, owned by the powerful Piccolomini family, the evolution of becoming a rich and prestigious city, depended on a descendant of this family, Enea Silvio Piccolomini, the future Pope Pius II, who appointed Bernardo Rossellino in 1459, one of the most important architects of that time, collaborator in Florence of Leon Battista Alberti, to build what was to become his "ideal city". In the year of 1462 - after only three years of work – the birth of the town of Pienza was celebrated, - while respecting the original structure of the medieval town centre, the city took the particular trapezoid shape and herringbone brick pavement, which overlooks the Cathedral, the Borgia Palaces, Piccolomini and Palazzo Comunale. This square is dedicated to PIO II.

Not too far from Pienza in the direction of Cassia, after only two or three km. you will come to the ancient church of Corsignano. It is more than a thousand years old, its circular bell and the decorations of the portal and the lintel are not to be missed. Also not to be missed is the small medieval village of Monticchiello, with its austere, beautiful gateway and the church of SS Leonardo and Christopher. Wonderful frescoes of the Sienese school of the XIII century.

Where to eat:

  • Trattoria "Latte di Luna" - Via S.Carlo n. 2/4, Pienza - 0578 748606
  • Osteria Baccus - Corso il Rossellino 70, Pienza - 0578 749080

Seventh day - Relax and rest at Podere Casanova

After so much touring, I recommend a day of relaxation, in tranquillity and silence of Podere Casanova!

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