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gaiole in chianti

Gaiole in Chianti: what to see, where to eat and sleep in the Tuscan countryside

The best restaurants, hotels, villages and castles of Gaiole in Chianti and surroundings

Located on the road that leads from Chianti to Montevarchi and Valdarno, about one hour from Florence, Gaiole in Chianti is another fundamental stop inside the Chianti Classico region, in the greenest heart of Tuscany. The whole Chianti area - which includes other small villages not to be missed such as Greve, Panzano and Radda - is rich in ancient finds. In fact, its origins date back to the Middle Ages, and in its square you can see the statue of a Black Rooster, symbol of Chianti.

The village, located along the course of the Massellone stream, has developed since the thirteenth century as a "market town" for the castles and neighboring towns, becoming one of the main towns of the League of Chianti, along with Radda in Chianti and Castellina in Chianti.

Gaiole in Chianti ph Dario Garofalo

Characterized by a position surrounded by steep hills and narrow valleys, in Gaiole originates the Road of Castles: among the most beautiful ones, the one of Cacchiano, the Castle of Brolio, Meleto, Vertine, San Polo in Rosso and the Castle of Ama, famous this last one - besides the production of wine - for the numerous works of contemporary art hosted inside.

In Gaiole is also indissolubly connected to L'Eroica, an evocative manifestation of the cycling of other times that has been able to conquer the attention of many fans all over the world. It takes place every year at the beginning of October, mostly on dirt roads in the area of Chianti Senese and the regulation provides that you take part riding a vintage bike.  There are two routes available: the long one of 205 kilometers and the medium one of 135. Departure and arrival right here.

ph Paolo Martelli


  • Chiesa di San Sigismondo
    Via Ferrucci, 14A
    ph. +39 0577 749434

Although it has a facade that was never finished and was built with the typical stone found in most ancient buildings, the Church of San Sigismondo dates back to the 1930s. Many of the works of art preserved inside are even more recent and are inspired by the medieval era, with the exception of the Paliotto with the Madonna del Rosario, a marble altar from 1699.

Chiesa di San Sigismondo Gaiole in Chianti

  • Piazza Ricasoli

This street-square has been for centuries the beating heart of the village, a place of commerce and daily life. The powerful Ricasoli family was very important for the entire Chianti region and in particular for Gaiole. It is possible to trace their lineage back to the Firidolfi family, which then changed its name to Ricasoli because they felt persecuted because of the noble origins of their lineage. The constant rivalry between Florence and Siena made the numerous castles they owned very vulnerable, but they have survived to this day and still adorn the vast surrounding landscape.

Piazza Ricasoli

  • Pieve di Santa Maria a Spaltenna

It is a 10-minute walk from Piazza Ricasoli, just away from the last houses in the center. Remembered since the first years of the XI century in some parchments of the abbey of Coltibuono. Between 1102 and 1110 the parish of San Pietro in Avenano was transferred to Spaltenna, which took the name of Santa Maria a Spaltenna and was transformed into a "munita" parish.  The name of San Pietro in Avenano was maintained until 1153 when, in the bull of Anastasio IV to the bishop of Fiesole, the church was mentioned by the pope as pieve of Santa Maria a Spaltenna. Next to the pieve there is the relative farm, restructured, with the monastic premises. Santa Maria a Spaltenna also became property of the Ricasoli family, already owners of the land and of the farm of the pieve of San Polo in Rosso. The interior is a Romanesque church, with three naves and an apse. The walls and the bell tower are made of alberese stone filaretti of cinerino color. The facade has a rectangular opening.

Pieve di Santa Maria a Spaltenna


  • Castello di Ama
    Località Ama in Chianti
    ph. +39 0577 746069

The art collection of Castello di Ama, where Grandi Vini di Terroir are produced, is set in a landscape of extraordinary beauty and focused on two fundamental notions: the in situ installation and the relationship with the genius loci. The works created by Michelangelo Pistoletto, Daniel Buren, Giulio Paolini, Kendell Geers, Anish Kapoor, Chen Zhen, Carlos Garaicoa, Nedko Solakov, Cristina Iglesias, Louise Bourgeois, Ilya and Emilia Kabakov, Pascal Marthine Tayou, Hiroshi Sugimoto, Lee Ufan, Roni Horn, Miroslaw Balka, are located between the modern winery and the complex composed by the ancient cellars, the eighteenth-century villas with their chapels, the gardens and the vineyards surrounding the village.

Castello di Ama - Gaiole in Chianti ph Lorenzo Cotrozzi

  • Castello di Brolio
    Località Madonna a Brolio
    ph. +39 0577 730280

The medieval heart of Gaiole and of the whole Chianti area is the Castle of Brolio, still today a symbol of the tradition and of the great viticultural history of Baron Ricasoli. The castle came into the possession of the Ricasoli family in 1141. Generations have traced its history: from the eternal battles with Siena to the unification of Italy. Bettino Ricasoli, the "Iron Baron", will be Prime Minister in the united Italy after Cavour, but also the inventor of Chianti wine. Still today the family is at the head of the oldest winery in Italy.

The Castle of Brolio, property of the Ricasoli family for over 850 years

  • Vertine

Medieval village that is found on a hill of 357 meters above Gaiole in Chianti. It rises to the extreme north-eastern offshoot of Chianti, behind a series of reliefs, called Monti del Chianti, which constitute the watershed with the Valdarno Superiore. This area is particularly rich in castles as it corresponds to the territory of the medieval Lega del Chianti, Florentine bulwark on the border with the territory of Siena. The splendid worked stones used for the construction of the walls and of the keep are also found in the internal buildings, the whole gives Vertine a typically medieval image and makes the visitor who walks along its narrow streets come back in contact with the reality of the past.

  • Castello di Meleto
    Località Castello di Meleto
    ph. +39 0577 749129 /+39 0577 749217

It rises majestically in the enchanting landscape of Gaiole in Chianti, at the end of a pleasant avenue flanked by cypresses and junipers. Since more than one thousand years, Castello di Meleto dominates its lands and vineyards. Custodian of a unique landscape in the world, the Castle and its charm unchanged over time give peace and tranquility to visitors. Today as in the past, Castello di Meleto is an uncontaminated oasis where to spend, surrounded by Tuscan hills, unforgettable moments. You cannot miss a visit to the rooms of the Castle and to the historical cellar. And if you want to experience an unforgettable stay there are also 19 rooms set in the unique context of a medieval castle and an outdoor swimming pool waiting for you.

Castello di Meleto

  • Borgo Castagnoli
    Località Torsoli, 21

It stands out from the heart of Chianti Classico, on a hill that Etruscans already knew very well, from there it dominates the surrounding valley from the top of a hillock that brings the mind back to ancient times, surrounded by woods, vineyards and olive trees. The Rocca that bears its name spreads on about 850 hectares of property with altimetric profiles ranging from 860 meters (hill of Monte Luco) to 380 meters. There are 92 hectares of vineyards, mainly cultivated with Sangiovese, which is the base grape of the finest Tuscan wines produced.

Borgo di Castagnoli

  • Greve in Chianti

Among the most famous villages of Chianti for scenic and culinary wonders, Greve in Chianti is one of the unmissable stops to get to know this beautiful area. Click here to discover with us what to do, where to eat and where to sleep in Greve in Chianti.

Greve in Chianti ph Dario Garofalo

  • Panzano in Chianti

If you want to breathe the quiet air of the hills and visit a medieval village where time seems to stand still, Panzano is absolutely for you. Click here to discover our special itinerary with restaurants, wineries and places not to be missed in Panzano.

the most ancient nucleus of Panzano in Chianti

  • Radda in Chianti

Also called the village of the vineyards, Radda in the heart of Chianti, is another little gem not to be missed to fully experience the colors and scents of the territory. To know what to do and where to eat in Radda in Chianti, click here.

Piazza Ferrucci with the Propositura of San Niccolò


Before discovering the restaurants not to be missed in Gaiole, click here if you want to know our selection of restaurants around Florence and here for that of the most beautiful wineries where to eat in Tuscany.

  • Osteria Al Ponte
    Via Antonio Casabianca, 25
    ph. +39 0577 744085

A traditional Tuscan osteria, ideal for a lunch of good Sienese cuisine. The restaurant is famous for its crespelle di baccalà mantecato, chickpea soup and the very tasty pork fillet with stewed onions. Also very good are the pici with light pesto and almonds and the fantastic pappa al pomodoro served with a seared eggplant and mozzarella roll. Among the main courses, of course, the Florentine steak but also the beef bites with Chianti sauce and rosemary potatoes. We end in beauty, and especially in sweetness, with panforte semifreddo with caramel sauce or pear pie with vanilla sauce and Vin Santo. There really is something for everyone.

Surrounded by the green hills of Chianti, Osteria di Brolio is the place where the flavors, scents and landscapes of Tuscany come together. A pleasant terrace is ready to welcome customers in the green, under the walls of the homonymous Castle of the Ricasoli family. Thanks to its desire to respect tradition and use quality raw materials, this restaurant is definitely a certainty for all those who seek genuine flavors under the watchful eye of Executive Chef Franco Sangiacomo, a well-known hospitality professional.

Osteria di Brolio

In the charming, romantic atmosphere of a millenary convent, whether you dine inside in the hall of the popes or at the tables placed in the suggestive internal courtyard you will be - in any case - in the reassuring hands of a young chef of Greek origin. Long in love with Tuscan cuisine, Chef Stelios Sakalis, will offer you a unique enogastronomic journey, between refined presentations, a remarkable research of products (especially among local breeders) and the ability to "translate" everything in a delicate and balanced way. A real Michelin star experience (click here to discover all the starred restaurants in Tuscany).

Il Pievano, Castello di Spaltenna

  • Osteria Il Papavero
    Località Barbischio 15 (Greve in Chianti)
    ph. +39 0577 749063

To reach Barbischio, a very old medieval castrum, you have to go up to the "upper floor" of Gaiole. You will find the Osteria Il Papavero, an ancient village store converted into a restaurant. The old floor of the small and unique room alone is worth the trip. The kitchen, on the other hand, offers a series of carefully prepared dishes that are never predictable, where the sensitivity of the chef-patron is revealed through the thoughtful reinterpretation of traditional dishes, sometimes playing "in subtraction", and demonstrating a sure hand in the cooking, balancing and planting. And if the wine list is a bit 'stringent, you'll still be able to drink well, especially if you rely on certain Chianti Classico of Gaiolese side.

Osteria Il Papavero

  • Ristoro di Ama
    Località Ama (Gaiole in Chianti)
    ph. +39 0577 746191

At the noble floor of the eighteenth-century Villa Pianigiani, we find the conviviality of Ristoro di Ama. The goal of Marco Pallanti, Castello di Ama's enologist since 1982, has always been to create wines that can be "drunk", without ever losing sight of the pleasure of being at table. Il Ristoro aims at combining wine tastings to a traditional menu where panzanella, pappa al pomodoro, potato ravioli with white meat sauce and Chianina beef steak stand out.

Ristoro di Ama


  • Capannelle
    Località Capannelle, 13 (Gaiole in Chianti)
    ph. +39 0577 74511

A wine estate which originated in 1974 when Raffaele Rossetti, a Roman entrepreneur, decided to purchase an old 17th century farmhouse in the heart of the Chianti Classico area. In 1997 Capannelle was bought by James B. Sherwood, founder of Orient-Express Hotels, Trains & Cruises (today Belmond Group). This led first to an expansion of the vineyards and then of the winery. Today the winery produces 5 types of wine, whose quality is constantly followed by Simone Monciatti, Capannelle's Enologist since 1984. Capannelle's wines are today distributed in 35 countries of the world.


  • Volpaia
    Località Volpaia (Radda in Chianti)
    ph. +39 0577 738066

Since 1172, great Chianti Classico wines have been produced here using organic farming methods. Listed among the three best wines of the world by Wine Spectator, Volpaia is known worldwide for the beauty of its cellars hidden in the walls of the ancient fortified village. Visiting the cellars of Volpaia is a unique experience that will take you through all the buildings and churches of the village. You should also try the Osteria and the Forno di Volpaia.



  • Villa Ricucci - Castello di Ama
    Località Ama in Chianti
    ph. +39 0577 746069

The beauty of staying at Villa Ricucci is to live a magical moment immersed in the world of Ama, kept with love and enriched by precious antique furniture, contemporary details and exclusive corners outside that always offer special moments. Five suites overlook one of the most suggestive landscapes of Chianti and Ama's vineyards and they take their name from them. To complete the experience, it is possible to discover Castello di Ama through a visit to the cellars, to the oil mill and to the collection of contemporary art that make the place unique.

Suite San Lorenzo - Villa Ricucci

  • Castello di Spaltenna Exclusive Resort & Spa
    Via Spaltenna, 13 - Località Pieve di Spaltenna (Gaiole in Chianti)
    ph. +39 0577 749483

Refined and welcoming 5-star charming relais located in an ideal position to visit the lands of Chianti Classico and to quickly reach the cities of Siena, Florence and Arezzo, and the most famous villages located in the heart of Tuscany. Four-poster or wrought iron beds, wooden desks, decorated curtains and chests of drawers with marble shelves populate the rooms, at Castello di Spaltenna luxury is synonymous with simplicity. Each room is different from the others but all are strictly in local rustic style, so that everything around you has the flavor of Tuscany.

Castello di Spaltenna Exclusive Resort & Spa

  • Dievole Resort
    Località Dievole 6 - Castelnuovo Berardenga (SI)
    Winery: 0577 322613 - Wine Resort: 0577 322632

An elegant wine resort located in the immediate vicinity of the medieval village of Vagliagli, in the municipality of Castelnuovo Berardenga, in the heart of Chianti Classico. Access to the estate is through an avenue of centuries-old cypress trees to the historic Villa Dievole and other recently renovated buildings. The origin of the name is picturesque, derived from "God willing", a reference to the small earthly paradise that constitutes the estate. 28 suites, double rooms and apartments, all renovated in the most elegant Tuscan style and equipped with all the comforts of an extra-luxury structure. Not to be missed is the gourmet restaurant Novecento for a delicious culinary experience and really suggestive is the infinity pool overlooking the vineyards.

Dievole Resort ph Mauro Puccini

  • Rocca di Castagnoli - Tenute Calì
    Località Castagnoli (Gaiole in Chianti)
    ph. +39 0577 731 909

The Rocca di Castagnoli estate, in the magnificent village of Castagnoli, has a wine relais with rooms and apartments with a refined style for sleeping in the most authentic Chianti, made up of rolling hills as far as the eye can see and ancient villages suspended in time. At the center of the millenary medieval fortress we find the Restaurant Il Celliere in Castagnoli. The cuisine has a very close link with the Tuscan tradition, without forgetting to leave room for imagination and innovation.

Tenuta La Rocca di Castagnoli

  • Badia a Coltibuono
    Loc. Badia a Coltibuono (Gaiole in Chianti)
    ph. +39 0577 749031 / +39 0577 74481

After the privatization of the abbey by Napoleon and the succession of several owners, Badia a Coltibuono has been in the hands of the Giuntini/Stucchi Prinetti family since 1846 and has become the first wine resort in Chianti, an undisputed point of reference for the quality and longevity of the wines, as well as for the respect of the territory, the attention to sustainability and the artisanal production method both in the vineyard and in the cellar despite the not small number of hectares and bottles. Perfect for a truly unique experience in the historic setting of an abbey dating back to 1051, and one of the cult of food and beauty in Chianti where you can taste revisited Tuscan recipes.

Badia a Coltibuon Resort


From Florence North: follow A1/E35 direction Terranuova Bracciolini, take the exit Valdarno, cross Montevarchi and continue to Gaiole in Chianti. Or take the Florence-Siena link road in the direction of Barberino Tavarnelle, exit at San Donato in Poggio and continue to Castellina in Chianti, passing the village of San Donato in Poggio and then turning towards Gaiole.

From Florence south: take the Via Chiantigiana, the scenic road that crosses all of Chianti from Florence to Siena.


You can either take the Florence-Siena freeway, exiting at Badesse and following the signs for Castellina, then continue on to Radda and finally Gaiole, or you can take SR 222 directly after Siena and follow the road to Castellina, Radda and Gaiole. For a shorter, but no less scenic, route, take SR 223 after Siena which leads to the Autostrada del Sole, exit at Cassetta-Monteaperti and then plunge into the surrounding countryside in the direction of Gaiole.

For parking, the closest to the center are the one in Via Michelangelo Buonarroti and the one in Piazza IV Novembre.

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