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        Scenic sunset over the Tuscan hills and historic architecture of Castellina in Chianti, Italy, showcasing breathtaking landscapes and charming vineyards.

        Castellina in Chianti

          Explore Tours

          Stacked Chianti Classico Black Rooster wine barrels in a Tuscan vineyard garden, visited on Super Tuscan tasting tour

           Florence, Italy

          Private Chianti Wine Tour: Black Rooster & Super Tuscan Wineries

          Uncork the real Tuscany — two family wineries, a homemade lunch in the Chianti hills, and a medieval village, all yours for a day.

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          From € 100.00
          Aerial view of blue and red classic convertible cars parked on green lawn in Chianti, Italy

           Siena, Italy

          Private Classic Car Tour in Chianti with Wine Tasting

          Discover Chianti the old-fashioned way — behind the wheel of a classic car, with a wine tasting at Castello di Brolio and a candlelit dinner to finish.

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          From € 850.00
          Close-up of Sangiovese grape clusters in Chianti vineyard, tasting tour to Castellina and Greve from Florence

           Florence, Italy

          Private Chianti Wine Tour from Florence – Full-Day Trip

          Skip the crowds and uncork the real Tuscany — a private day through vine-draped hills, ancient hilltop villages, and the organic estates that make Chianti Classico legendary.

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          From € 68.00
          Iconic black rooster statue with giant wine bottle and terracotta jar marking Chianti Classico wine region on Good Morning tour route

           Florence, Italy

          Chianti Classico Private Tour: 2 Wineries & Lunch in Tuscany

          Wake up to Tuscany at its finest — rolling vineyards, two world-class wineries, and a long Tuscan lunch, all before the afternoon begins.

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          From € 80.00
          Three people smiling beside supercars with Chianti vineyard hills in background, Siena Italy

           Siena, Italy

          Private Supercar Tour in Siena with Chianti Wine Tasting

          Race through Chianti in a private supercar, sip world-class wines at a medieval castle, and end the day with dinner in the Tuscan hills — this is Italy at its most extraordinary.

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          From € 1930.00
          Close-up of ripe Sangiovese grapes in a Chianti vineyard on a Tuscany wine tasting day trip from Rome

           Rome, Italy

          Private Guided Chianti Wine Tour & Castellina from Rome

          Escape Rome for a day and lose yourself in the sun-drenched hills of Tuscany, where world-class Chianti wines, ancient hilltop villages, and a private luxury experience await you.

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          From € 85.00
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          More to know about Castellina in Chianti

          Castellina in Chianti is a medieval hilltop town in Tuscany, central Italy, surrounded by renowned vineyards in the Chianti Classico region. The town features narrow winding streets, a 16th-century fortress, and the underground Etruscan tunnel system known as the Strada Coperta. Visitors explore the historic center, visit local wine cellars for tastings, and hike through the surrounding vine-covered hills.
          Castellina in Chianti is a hill town in the Siena province of Tuscany, Italy, situated within the Chianti Classico DOCG wine zone at approximately 580 metres above sea level, roughly 22 km from Siena and 35 km from Florence. This guide was prepared by the ToursXplorer Editorial Team using publicly available destination data and field knowledge of the region.
          Chianti Classico, Tuscany, Italy, Medieval Hill Town, Wine Region, Etruscan Heritage, Agriturismo