Introduce your family to the magic of Tuscany as we explore walled villages, old fortresses, and breathtaking landscapes. From our base at a lovely villa in Chianti, set out on daily adventures, discovering medieval alleyways and castle keeps, peering at famous frescoes with an art historian, and hiking through the beautiful Tuscan countryside.

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After breakfast, visit the Benedictine church of San Miniato al Monte, perched picturesquely above Florence. Take advantage of this bird’s-eye view of the city to capture the sweep of red-tiled roofs and the iconic dome designed by Brunelleschi. Then drive into through the hills to Greve in Chianti, where we’ll wander with our cameras through vineyards dangling with ripening grapes and the sample the region’s celebrated wines. Set off on a photo hike to the fortified village of Lamole. After a lunch of local specialties, take a short drive to Volpaia, a fortified village where the famed Chianti Classico wine is produced. From here, depending on the terrain, we’ll continue on foot to the Romanesque church of Santa Maria Novella and photograph the historic site in the golden light of late afternoon. Our home for the next two night is a charming hotel in Radda in Chianti’s center.

Today’s hike winds through vineyards and fields to the medieval town of Panzano, known for its traditional cured meats. Photograph panoramic views of the valleys below as we continue to the Badia a Passignano vineyard abbey, home to a 15th-century fresco of The Last Supper. If you wish, choose a more challenging hike back to our hotel.

With its winding lanes, Gothic churches, and redbrick palaces, Siena begs to be photographed. Spend the morning exploring with your camera. Capture the jarring contrast of black and white marble in the cathedral, and frame the graceful curves of the great central piazza, Il Campo, known for the medieval horserace that continues today: il Palio. Then visit Monteriggioni, a well-preserved walled village mentioned in Dante’s Inferno, and photograph its evocative ramparts and towers.

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