Chianti is Tuscany’s wine region, and it is world famous for the signature Chianti Classico wine. The unique landscape is made up of gentle and green hills c

Screen Shot 2016-10-14 at 16.05.19overed with vast vineyards, small stone villages, olive groves, countryside homes made of stone, and parishes with their unique character. The beauty of Chianti’s landscapes is evident in many photographs found in numerous calendars and postcards around the world.

It is very hard to give precise borders to the Chianti area in Tuscany. This is because the name of Chianti is traditionally referred to as the area between Florence and Siena where Chianti wine is produced and not a definite territorial area with boundaries. With time, the area where Chianti wine is produced has grown.

The map to the right, is just to give you a rough idea of what is traditionally considered Chianti. The comunes that traditionally are considered part of Chianti are: Greve in Chianti, Radda in Chianti, Gaiole in Chianti, Castellina in Chianti, Panzano in Chianti, Castelnuovo Berardenga, Impruneta, San Casciano Val di Pesa, Tavernelle Val di Pesa.

Some of the most wonderful and historic villas for sale are in Chianti. Most dating back to the 16th and 17th century and are built entirely from stones and ancient terracotta. You can expect villas to be surrounded by olive trees and vineyards. They typically have large outdoor spaces with breathtaking views where you and your guests can feast on meals al fresco, or simply relax.



Greve in Chianti

Greve in Chianti is one of the most desirable locations in all of Chianti. It is known as the “gateway” into the Chianti region. this lively town is famous for its particularly shaped piazza or square that has been market place for the castles and walled villages in the surroundings since the Middle Ages. The square has a triangular shape and large porticos along three sides that protect from sun and rain while shopping. In the center stands the bronze statue of Giovanni da Verrazzano, explorer that discovered the Bay of New York. At the top of the square stands the Church of S. Croce, originally a medieval church remodeled according to Renaissance Revival architectural style, displays a few precious works of sacred art including the triptych depicting Madonna and Saints by Bicci di Lorenzo.

Greve presents many different places where you can taste Chianti wine and enjoy local food. The porticos host many workshops, wine bars and restaurants. One that requires mentions is the Antica Macelleria Falorni ( a historical butcher shop that sells only typical products produced in Chianti. Just a few steps away stands the Wine Museum which we recommend visiting. Another restaurant that respects the tradition of the region is the La Castellana ( with only a few tables and a fine cuisine made from passion, tradition, simplicity and genuine taste. Everything served is prepared with fresh and seasonal ingredients from the region.

In the region, you can find good hotels with all the facilities you could need, for example the Villa Bordoni (, which is a 5 stars hotel that was voted, in 2006 and in 2007, one of the “Best New Hotels in the World” by Condé Nast Traveller. Nearby is also Castello Vicchiomaggio ( which is a castle turned in to a luxury hotel. 

For the sports facilities, nearby you have the famous Circolo del Golf Ugolino ( wich is one of the best golf clubs and resorts in all of Tuscany.

Every year on the second weekend of September the city does the Chianti Classico wine festival that is biggest festival in the town where you can try and buy the bests wines of the region. Another annual festival that you can find in the town, is the “Mercatini di Natale” Christmas markets, that happens every year during the Christmas.

Radda in Chianti

Radda in Chianti is a gorgeous medieval town which is surround by large defensive walls. Because of these walls, the city was in isolation for a long time. However today we can be glad about that because it has thoroughly retained its ancient appearance, the same as it was in the middle ages; filled with maze-like streets and incredible ancient architecture and ruins. The Palazzo del Podestà overlooks the main square together with the Romanesque Church of S. Niccolò. The Palazzo was the headquarters of the Chianti League for over four centuries, as confirmed by the many coats of arms on its facade. It is really nice to get lost in Radda wandering around its medieval streets, drinking a glass of wine while looking at the spectacular panorama of the vineyard covered hills that surround the town.

Near Radda stands the Castle of Volpaia, an ancient walled town which we recommend visiting. The castle in sandstone has a distinctive dark color that makes it different from other castles in Chianti. In spite of the marks and damage from the numerous wars between Florence and Siena, the main structure can easily be recognized by its massive tower. We also recommend stopping at the Commenda of S. Eufrosino, a 14th century church transformed into a wine bar.

You can find many places to enjoy traditional food and wine of the region, an example will be the La Vin Osteria ( which is a very traditional restaurant offering fine gourmet from the region and also there is La Botte di Bacco ( there you will find colorful dishes, which remind of the ancient yet modern Tuscany in every bite.

In Radda you can find traditional hotels to stay, like the CDH Hotel Radda ( which mixes the modern with the classic traditional and there is also the Villa Campomaggio Resort & SPA ( surrounded by vineyards and woods.

If you like to golf, nearby is the prestigious golf club  Ugolino (

Every year on the last weekend of May,  in the town of Radda in chianti there is a festival called Radda Nel Bicchiere. It is a weekend wine festival that takes place in the main streets and piazza of the town and features wineries and wine producers that are only near this village. This is one of oldest wine festivals of the Chianti area and every year attracts producers, bloggers, locals and tourists.


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Gaiole in Chianti

Another town dating back to the Middle Ages, Gaiole was an important market place for the castles in the surroundings because of its position between Chianti and the Valdarno (Valley of the Arno river). Gaiole is still an important point of interest in this area. As a matter of fact, you can find many farmhouses, wine shops and wineries in the area which is perfect for wine tasting as well as lodging for your holidays.

Screen Shot 2016-10-14 at 17.20.49There are many castles and fortified towns around Gaiole that deserve a visit. For example,  Castle of Vertine (, and  Castle of Meleto (

In Gaiole you can also find exquisite hotels and resorts. For example Castle of Spaltenna ( is a luxurious hotel and hosts a wonderful Michelin star restaurant named Il Pievano, where you can find the most exquisite gourmet in the area.

Another option where  you can find perfect accommodation with restaurants and activities is the Le Pozze di Lecchi (, a 4 star hotel with everything you need and has a splendid restaurant called Monna Ginevra, wine tastings, swimming pool and other facilities.

For Golf lovers, nearby is The Royal Golf La Bagnaia ( which was the first gold course built in Tuscany, 18 holes designed by renowned architect Robert Trent Jones, Jr. The course is enhanced by beautiful lakes and a majestic Club House.

In the summer, a series of events come to life in Gaiole, in particular, on the 17 of July there is the “Festa di San Sigismondo” and coinciding with this date is also the Festa dei Rioni; both playful and gastronomic events with Summer concerts, markets and food stands. Another event, is the Eroica in Gaiole in Chianti, a legendary bike race that happens in October, but this festival is not for the faint-hearted, as its name suggests: eroica means “heroic.” This race winds along the white roads of Chianti in pursuit of the “beauty of fatigue” and the “thrill of the conquest.”

Castellina in Chianti

Moving towards Siena you’ll reach Castellina in Chianti, which dates back to the Etruscans, as attested by the Etruscan tombs of Montecalvario. Its great position in the middle of the Chianti region, made Castellina a strategical headquarter between Florence and Siena. Confirming this glorious past, is the massive Rocca (castle) that stands proudly over the city and the impressive Via delle Volte, an underground tunnel around the city. Walking through the small town you will notice many historical buildings that belonged to Florentine and Senese aristocracy. The Church of S. Salvatore merits a visit; rebuilt after the Second World War, the church displays a beautiful late 14th century fresco by a Tuscan master. We also recommend the Archeological Museum of Chianti Senese ( where many archeological findings from the Chianti region, and particularly Etruscan findings from Montecalvario, are displayed.

In Castellina in Chianti you can find amazing places to eat, one really good example is the Albergaccio di Castellina ( which is a rustic tuscan restaurant mixed with high classe elegance and quality. Another really good option is the Foresteria Villa Cerna ( famous for its wine tastings.

Like all the towns in the Chianti area, here you will find luxurious hotels to enjoy. One good option will be Locanda Le Piazze Toscana ( a 4 star boutique hotel in Tuscany, which is a former farmhouse dating back to the 1540. It sits among the soft hills, surrounded by olive groves, vineyards and cypresses. Otherwise, you can also enjoy the Hotel Belvedere di San Leonino ( which is in the open countryside, surrounded by its vineyards and by the Chianti hills that slope gently to the outskirts of Siena.

In 40 minutes driving, you can reach The Royal Golf course La Bagnaia ( and enjoy the 18 hole course designed by renowned architect Robert Trent Jones, Jr. The course is enhanced by beautiful lakes and a majestic Club House.

The most important festival in Castellina in Chianti is called Fiera del cocomero (Watermelon Fair). The old town is transformed into a huge market where local products, antiques and crafts are on sale from morning until the evening of August 24. The Watermelon Fair hosts food stands, live music and dancing in the Piazza del Comune.

Another good festival is the Pentecost in Castellina which is a summer festival dedicated to wine that for the last 15 years has been bringing together the best wineries in Castellina in Chianti, beneath the picturesque walkway of Via delle Volte and the medieval village.

Panzano in Chianti

Panzano is one of the most popular towns in Chianti and is located halfway between Florence and Siena. This town is nice because it is far away from the crowds of tourists but still conveniently close to both major tuscan cities. This 12th century town, played an important defensive role for Florence and its county. The Castle of Panzano was fundamental for defending the Florentine Republic during the battles between Florence and Siena. The castle’s structure can be still recognized within the older section of town including the Church of S. Maria, which dates back from 1200 even if it was completely rebuilt in the 1800s in Neoclassical style.

It is really nice to wander through the old town, soaking the atmosphere of times gone by and sitting in the main square drinking a glass of Chianti wine. There are several wine bars and restaurants in Panzano that offer wine tasting, Undoubtedly equally noteworthy is the Old Butcher Cecchini from Dario Cecchini. World known and admired for his T-bone steak. ( His restaurant is a must for those staying in Panzano, known to the point of being frequented often by celebrities, including actors like Jack Nicholson. Another great option in the city, is the Il Vescovino a family owned restaurant with a splendid view.

Screen Shot 2016-10-14 at 17.18.45The location also offers few prestigious options for hotels, like Villa Le Barone Hotel ( which is a 4 star charming luxury hotel who affords unparalleled views of the surrounding olive groves, vineyards and rolling hills of Tuscany.

Close to Panzano in Chianti, is also the splendid golf club Ugolino ( where you can enjoy your time in one of the most traditional golf clubs in Tuscany.

On the 25th of April (Italy’s National Holiday) happens the Festa della Stagion Bona, the beginning of the “good season” with a procession in historical costumes of the Renaissance era, a medieval play and plenty of stands with ready-cooked food.

Also, every year, on the third weekend of September, the vintners of Panzano meet in the village square to show their wines, in a festival called Vino al Vino Panzano. You have the chance to sample the different styles of wines, chat with the winemakers and listen to some great jazz.

Castelnuovo Berardenga

Lying in the hills of Tuscany and located in the Province of Siena lies the secluded treasure that is Castelnuovo Berardenga. With Siena being 14 kilometers to the west, it offers an extraordinary view, as Siena sits on the horizon. Castelnuovo Berardenga is thought of as the southern boundary of the Chianti wine zone.

This town has layers of history as there are some churches dating back to the year 600 CE. Over the years, many noble families have built remarkable villas and gorgeous luxury homes which really adds to the unreal essence that the city has to offer. One of the best things to do is to explore its many narrow streets and its back alleys. This can be only done on foot since these streets are too narrow for cars.

Eating out here is quite enjoyable for two reasons, first being that the region of Chianti produces some of the best wines in Italy and second being that the town’s main industry is agriculture. Most restaurants in the region use fresh ingredients that are locally grown and create home style dishes that are typical to this region. One of the bests restaurants is the Le Pietre Vive ( Another option is the Bengodi Enoteca & Ristorante ( which counts on a rich cuisine and selected flavors of the region.

As far as luxury accommodations; Borgo San Felice ( is a magical oasis in which you can experience the emotions of Tuscany. It is a 5 star hotel, located on a hill 400 meters above the sea, surrounded by 140 hectares of vineyards. The city also counts with another incredible option, a 4 star hotel called Borgo Scopeto Relais ( that has stunning views of the city of Siena. A corner of paradise with views over the Mangia Tower and the cathedral’s belfry which, together with the rolling Chianti hills, create a setting of luminous beauty.

If you enjoy doing sports, in only 25 minutes you can reach the The Royal Golf La Bagnaia (, a golf club with courses that are enhanced by beautiful lakes and a majestic Club House. Offers an 18 hole course designed by a renowned architect.

A good experience that happens every month of october in the city, will be The Dit’unto festival that is dedicated to the pleasures of eating with your hands (its name means “wet finger”). Taste the best of Tuscan cuisine in all its rustic splendor as well as the heights of Michelin-starred chefs.

Another event during the same month is The Ecomarathon of Chianti marathon that departs from the Castle of Brolio, and continues for three different options: 14 km, 21 km, or 41 km. The finish line is in the “Slow City” of Castelnuovo Berardenga.


The city of Impruneta is less than thirty minutes and only 15 kilometers from the city center of Florence and has a population of a mere 15,000. The name “Impruneta” is derived from the latin word “imprunetis” meaning “within the pine woods”.  The city is best known for the excellence of its terracotta handicraft, both decorative and practical in function. The town is also the location of one of the most famous basilicas in Tuscany, the Sanctuary of Santa Maria, dating back to 1060 and immortalised by Jacques Callot.

During the Autumn, every year, the town hold an excellent grape festival with floats and parades.

You can also find fantastic options of accommodations around here, like the Relais Villa L’olmo, ( which perfectly captures the authentic and genuine Chianti lifestyle.

To appreciate the wine and food of the region, you have good options. The restaurant I Tre Pini ( is an an excellent choice because they make the dishes using the ingredients of the season and from the local producers. So you will always find fresh food with high quality. Another traditional option is the Bellavista (http://www.bellavistaimpScreen Shot 2016-10-14 at a restaurant with 110 years of history. The menu is seasonal but with some typical dishes available year-round, such as the renowned Florentine steak or the award-winning beef stew (peposo).

For the golf lovers, the Circolo del Golf Ugolino ( is one of the best golf clubs in the region, and it is only 10 minutes from the city.

Impruneta has some festivals during the year, like The Grape Festival is a festival that takes place every last Sunday of September, the festival is not a common village feast, but it is a sheer allegory of the Grape, where each district of the town gives off its own creativity in celebrating this marvellous fruit. The festival celebrates the harvest of the grape with a large market including shows, music, local food and wine tasting.

Another option during the Autumn is the Fiera di San Luca on October, if you’re into folklore and long-held traditions, then the Fair of Saint Luke is the event for you. One of the oldest livestock fairs in all of Europe. 

San Casciano Val di Pesa

This is another one of the many hidden jewels found inside the province of Florence. The town is thickly surrounded by tall evergreens and farms giving it the authentic Tuscan “feel”. San Casciano is home to an array of churches and castles. The Pieve of San Pancrazio is located on a hill dividing the valleys of Pesa and Virginio. The Castle of Bibbione is another impressive structure, as well as the Castle of Gabbiano and the castle of Pergolato. San Casciano is highly renowned for its production of wine and oil. The main cellars of the world famous wine company “Antinori” are established in San Casciano.

The town is truly a tourist friendly little town, as well as a very lived town. Little boutique shops, lots of cafes, restaurants and gelato places line the busy little town center. Using San Casciano as your base, has you in the middle of practically everything.

The town and the surroundings offer many restaurants, trattorie and pizzerie where you can taste traditional Florentine and Tuscan food. A special option for those who like refined dining is La Tenda Rossa ( with a special selection of wines and an excellent cuisine. If you want to try the classic Bistecca Alla Fiorentina (fiorentin bistek), we recommend you try the Cinque di Vino restaurant (

As in other cities in Tuscany, San Casciano Val di Pesa has special options for accommodations. Villa il Poggiale, ( a 4 star hotel surrounded by vineyards and olive groves with the landscapes seen in famous Tuscan Renaissance paintings. There is also Villa Magiacane ( that has luxurious facilities complementing the private villa, including two swimming pools, unique sculpture gardens and breathtaking Tuscan views.

In just half an hour driving you can enjoy memorable moments in the sports facilities from the Golf camp called Circolo del Golf Ugolino ( One of the best golf clubs in the region.

For 12 years in San Casciano in Val di Pesa happens the “Alla corte del vino” “At the wine court” an important exhibition market of high quality Tuscan wines at the historic Villa Le Corti.

Another festival is held in the town every June, dedicated to a small but very savoury fruit: the pine nut. Ten days of music, entertainment for children and grown-ups, fireworks displays and obviously many, many delicious pine nut recipes, including the renowned pinolata cake. Another annual festival that you can find in the town, is the “Mercatini di Natale”  the Christmas markets, that happen every year during the Christmas.

Tavarnelle Val di Pesa

Tavarnelle Val di Pesa is a village located at 378 meters above sea level in the Chianti hills of the Florence province. It is mostly modern architecturally but is also the location of the Church of Santa Lucia al Borghetto, being a rare example of Tuscan Gothic architecture.

Screen Shot 2016-10-14 at 17.23.57Nearby there are several extremely interesting structures, notably the parish church of San Donato in Poggio, the parish church of San Pietro in Bossolo which now houses the Museum of Religious Art of Tavarnelle, and the large and important monastery of Badia a Passignano.

This small town in the middle of Tuscany has an amazing 5 star hotel named Castello del Nero Hotel and Spa  ( that has a privileged position in the verdant Tuscan countryside. This luxury accommodation is a magnificent 12th century castle offering stunning views of the rolling local hills, ancient vineyards and lush olive groves.

Here you can also find a 4 star hotel, named Hotel Borgo Di Cortefreda Relais ( which is a charming place that combines elegance and style with the true philosophy of wellness. A dreamlike atmosphere with the comfort of the highest level.

In Tavernelle, besides amazing hotels, you can find amazing restaurants. One great option is the traditional Osteria La Gramola ( that serves authentic Tuscan cuisine. Besides this, there is also the Osteria di Passignano ( that represents the regions tradition and passion for wine.

Since the town is really close to Florence, you can enjoy many sports facilities, like the Circolo del Golf Ugolino (, one of the best golf clubs in the region. People say that to play in Ugolino is not just to indulge in a game of golf, it is to wander through a landscape of great natural beauty, surrounded by olive and other fruit trees.

Festival di Pentecoste is a music festival that happens every year here in June, and has the mixture of classic, high-profile art and culture in the Chianti region. You will find concerts with violin, pianoforte and others.

Wine tasting and olive harvest season

 Chianti is one of Italy’s prime wine regions. The best way to tour the wineries and sample their products is on the last Sunday of May when many producers throughout Italy open their doors for the festival of Cantine Aperte. Tastings are free and reservations unnecessary, so if you like wine and happen to be in Tuscany at the time, this is a fantastic opportunity for you.

Olive groves are also the region’s pride, and while it is not normally possible to visit an oil press, olive oil can be purchased directly from the producers. Olives are pressed in November and December.

Helicopter tour of Chianti

If you want to see some of the best sights of the region, you can take a helicopter day trip to Chianti from Florence, which starts with a helicopter tour of the area and then continues with a guided tour of the countryside, wine tasting and a dinner at a famous local restaurant.


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