Gaiole in Chianti Holidays

This ancestral seat of the Ricasoli family since 1141 stands as Italy's oldest winery, pivotal in Chianti Classico's development. Stroll through formal gardens before sampling estate wines in historic cellars.

This 11th-century abbey turned winery showcases Tuscan history through frescoed rooms and gardens. Sample organic Chianti Classico wines and savour traditional cuisine made with estate-grown ingredients.

This 11th-century Tuscan fortress houses an unexpected 18th-century theatre among its medieval walls. Tour the historic wine cellars and conclude with a tasting of the estate's renowned Chianti Classico wines.

This 16th-century Tuscan estate crafts organic Chianti Classico using traditional methods. Tour the historic cellars before savouring wine and olive oil tastings with the Cantalici brothers.

This medieval watchtower once guarded Chianti's rolling hills as part of Florence's defensive network. Explore the ancient walls and savour panoramic countryside views from its strategic hilltop position.

This 11th-century castle invites you to explore noble rooms, ancient cellars, and an 18th-century theatre. Conclude your visit with a guided tasting of their renowned Chianti Classico wines in the atmospheric enoteca.

This local sports venue serves as the athletic heart of Gaiole in Chianti. Visitors can catch regional football matches while experiencing authentic Italian community spirit.

This 1930s stone church houses a remarkable 1699 marble altar featuring the Madonna del Rosario. Visit in morning light to appreciate its medieval-inspired artworks and tranquil atmosphere.