Virtually the only thing we dislike about Tuscany is going there with a return ticket. There are few more agreeable ways to spend time than strolling through the great cities of Lucca, Pisa and Siena. But the supreme pleasure is puttering along country roads through one of the most distinctive and civilized landscapes in the world. A patchwork of wine and olive estates dominates the hilly Chianti district, a 40-mile swath between Florence and Siena. Memorable sites include the picture-book wine villages of Castellina, Radda and Volpaia, plus the 13th-century fortress hamlet of Vertine; the ancient abbey-wine estate of Badia a Coltibuono (8 miles east of Radda); and majestic Castello di Brolio (13 miles southeast of Radda, near San Regolo). Outside the Chianti Classico area lie the dramatic walled town of Monteriggioni and the picturesque medieval city of San Gimignano. The scenic Val d’Orcia wine region of southern Tuscany begins 45 minutes southeast of Siena, its vineyards producing celebrated reds such as Brunello di Montalcino and Vino Nobile di Montepulciano.
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