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Castellina In Chianti Holidays

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Medieval charm amid the vineyards

The medieval village of Castellina In Chianti perches on a ridge among rolling vineyards and cypress trees between Florence and Siena. Its idyllic location mean Castellina In Chianti holidays give you easy access to a scattering of romantic Tuscan towns, where you can wander the pretty lanes to enjoy the hospitality of its family-run trattorias.

Among the village’s streets you’ll find centuries-old architecture, including the neo-Romanesque San Salvatore church and a choice of authentic cafés and boutiques on the pedestrianised Via Ferruccio. Day trip possibilities also include Badia a Passignano, a hilltop Benedictine abbey dating back more than 1,000 years, and the medieval castles and churches around Gaiole in Chianti. As their names suggest, the region’s towns are proud of their prime location in the Chianti wine region, and holidays to Castellina in Chianti aren’t complete without tasting its bounty.

Exciting tours and activities

From priority access for attractions, to day trips to historic sites, here’s our must see activities in Castellina In Chianti

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Explore our map of Castellina In Chianti

Why book with us?

    Your Castellina In Chianti questions, answered

    Seek out traditional trattorias for home-cooked Tuscan cuisine, down-to-earth osterie for affordable farm-to-table feasts and enoteca wine bars for a glass or two of Chianti.
    Tuscany is one of the world’s great culinary destinations. Look out for ‘bistecca alla fiorentina’ (chargrilled T-bone steak), Livorno fish stew, truffles and wild boar.
    Hiring a car or Vespa is the best way to explore the region, but there are regular buses to nearby Radda in Chianti and Siena.