There are places that seem to have stepped straight out of a postcard. Winding roads lined with endless vineyards, medieval hilltop villages, golden sunsets and tables laden with some of Italy’s most authentic flavours. Welcome to Chianti, the romantic heart of Tuscany.

The flawours of chianti: wine, olive oil, cured meat and local specialities

To speak of Chianti is, inevitably, to speak of wine. The world-famous Chianti Classico, instantly recognisable by its iconic Black Rooster (Gallo Nero) emblem, has shaped the history and identity of these rolling hills for centuries.

Many wineries and family-run estates offer guided tastings, giving visitors the opportunity to discover every stage of the winemaking process while sampling exceptional wines, extra virgin olive oils, traditional cured meats, Pecorino cheeses and many other local delicacies.

Among the region’s finest culinary treasures is the prized truffle, the star ingredient of countless traditional dishes that reflect the deep connection between these lands and Tuscany’s rich gastronomic heritage.

From Castellina in Chianti to Radda in Chianti, Gaiole in Chianti and Greve in Chianti, this itinerary explores some of Tuscany’s most enchanting villages, combining outstanding food and wine experiences with charming places to stay surrounded by unspoilt countryside, where life naturally slows to a gentler pace.

Castellina in Chianti: timeless charm among the sienese hills

Castellina in Chianti is one of the jewels of the region. Strolling along the atmospheric Via delle Volte, exploring its beautifully preserved historic centre and browsing its independent artisan shops is the perfect way to experience the true spirit of Chianti.

The surrounding countryside offers breathtaking scenery, while its panoramic roads are ideal for cycling through vineyards and rolling hills

Where to stay in Castellina in Chianti

Hotel Belvedere di San Leonino
Surrounded by vineyards, olive groves and woodland, Hotel Belvedere di San Leonino enjoys an exceptional location in the heart of the Chianti Classico region. The hotel boasts magnificent views stretching as far as Siena, Monteriggioni and San Gimignano.

Its elegant rooms retain all the character of traditional Tuscan architecture, with exposed wooden beams, terracotta floors and warm, welcoming interiors. It is an ideal retreat for couples seeking romance, relaxation and an excellent base from which to explore Tuscany.

Villa Gran Sogno
A true oasis nestled among the hills of Castellina, Villa Gran Sogno effortlessly blends contemporary elegance with authentic Tuscan character.

Its panoramic swimming pool, beautifully landscaped gardens, peaceful relaxation areas and highly personalised hospitality create an exclusive holiday experience. Guests can also enjoy cookery experiences, visits to local markets and guided excursions through the surrounding countryside alongside the owners.

A sweet stop in Castellina in Chianti
After a day spent exploring vineyards and medieval villages, there is only one place to indulge your sweet tooth: Gelateria di Castellina.

Renowned for its handcrafted ice cream made with carefully selected ingredients, it offers flavours inspired by the finest local produce — the perfect way to cool off while wandering through the historic centre.

Radda in Chianti: the village of wine and traditions  

Radda in Chianti is perhaps the village that best preserves the medieval soul of Chianti. Its ancient walls, narrow stone streets and sweeping views across the surrounding hills make every stroll unforgettable.

Wine is woven into everyday life here, and many wineries welcome visitors for guided tours and tastings.

A must-visit in Radda in Chianti: Casa Porciatti

If you would like to take a taste of Chianti home with you, Casa Porciatti, is an essential stop. 

This historic delicatessen and wine merchant, located in the heart of the village, offers artisan cured meats, Tuscan cheeses, preserves, local delicacies and an expertly selected collection of regional wines.

Gaiole in Chianti: nature, wine and truffles

Gaiole is the perfect destination for lovers of the countryside, outdoor activities and exceptional food and wine.

Here you will discover some of the most iconic landscapes of Chianti Classico, with medieval castles, white gravel roads and spectacular vineyards creating the unmistakable geometric patterns that define this remarkable landscape.

Where to stay in Gaiole in Chianti

Azienda Agricola La Montanina
In the tiny hamlet of Monti di Sotto, La Montaninawelcomes guests to charming apartments surrounded by nature.

This family-run estate produces Chianti Classico DOCG wines and organic extra virgin olive oil, making it the perfect place to experience rural Tuscany from the inside through tastings and genuine country hospitality.

Montelucci Chianti Agrivilla

A beautifully restored country residence set amidst the peaceful Chianti hills. Its panoramic swimming pool, pristine natural surroundings and tranquil atmosphere make Montelucci Agrivilla an ideal retreat for anyone seeking a restorative escape in the heart of Tuscany.

Where to eat in Gaiole in Chianti: the kingdom of truffles 

La Locanda del Tartufaio

For lovers of authentic Tuscan cuisine, the La Locanda del Tartufaio is an absolute must.

Truffles take centre stage throughout the menu, featuring in appetisers, homemade pasta dishes, carefully selected meats and seasonal specialities. Every course celebrates one of Tuscany’s most prized culinary treasures.

Greve in Chianti: the gateway to Chianti Classico

Greve is often regarded as the capital of Chianti. Its famous Piazza Matteotti, with its distinctive triangular shape, is the lively heart of the town, surrounded by wine bars, specialist food shops, cafés and year-round events celebrating local wine and gastronomy.

Where to stay in Greve in Chianti

Casa Vacanze Alessandro
Located in the centre of Greve in Chianti, Casa Vacanze Alessandro offers beautifully renovated apartments in traditional Tuscan style, generous outdoor spaces and every comfort needed for a completely independent holiday.

Its central location makes it easy to explore the village’s restaurants, artisan shops and attractions on foot. Guests also enjoy exclusive benefits at the nearby "La Cantina Restaurant".

Where to eat in Greve in Chianti

La Cantina Ristorante
In the heart of Greve, La Cantina serves traditional Tuscan cuisine in a warm and welcoming atmosphere.
The menu ranges from local specialities to freshly prepared pizzas, all complemented by an excellent selection of regional wines. It is the ideal choice for a relaxed dinner after a day of wine tastings and sightseeing.

Ristorante La Castellana
Overlooking the enchanting village of Montefioralle, one of Italy’s most beautiful historic villages, Ristorante La Castellana serves classic Tuscan dishes prepared with high-quality local ingredients, all accompanied by spectacular views across the surrounding hills.
It is a place where outstanding cuisine and unforgettable scenery come together perfectly.

A  journey to savour with all your senses

A visit to Chianti is about far more than simply admiring beautiful landscapes. It is an invitation to immerse yourself in the timeless charm of medieval villages, discover centuries-old traditions and savour one of Italy’s richest food and wine cultures.

Whether you are planning a romantic escape, a wine-tasting weekend or a culinary journey through Tuscany’s most authentic flavours, every road — from Castellina to Radda, from Gaiole to Greve — leads to an unforgettable experience. Come and discover it for yourself!