The Chianti region between Siena and Florence is one of the world's great wine landscapes, a rolling terrain of cypress-lined roads, medieval castle estates, sunflower fields, and vine-covered hillsides producing the Sangiovese-based Chianti Classico that has defined Tuscan wine for centuries. The Strada del Chianti Classico winds through the villages of Greve, Panzano, Radda, and Gaiole, each with its own winery, enoteca, and artisan food producers. Hotels in Siena offer day trips into the Chianti by car or guided wine tour, combining the city's medieval grandeur with the pleasures of the Tuscan countryside.
Our Picks — Siena
Piazza del Campo
Siena's only 5-star in historic 16th-century palazzo near Piazza del Campo with frescoes and wine cellar.
Many rooms include free cancellation
Piazza del Campo
Elegant boutique in medieval building near Campo with antiques, wine cellar, high traveler ratings. A 4-star property that delivers quality and character in equal measure.
Many rooms include free cancellation
Terzo di Camollia
Luxury boutique with frescoed ceilings and premium local breakfast steps from Piazza del Campo. A 4-star property that delivers quality and character in equal measure.
Many rooms include free cancellation
Near Porta Romana
Charming historic B&B in heart of Siena near Duomo with exceptional cleanliness and service. A 4-star property that delivers quality and character in equal measure.
Many rooms include free cancellation
Terzo di San Martino
Modern 4-star with panoramic views, restaurant, parking, short walk to Campo and Duomo. A 4-star property that delivers quality and character in equal measure.
Many rooms include free cancellation
Near Duomo
Luxurious 14th-century monastery retreat with pool, tennis, gardens just outside Siena walls. A 4.5-star property that delivers quality and character in equal measure.
Many rooms include free cancellation
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