A patchwork of wine and olive estates dominates the Chianti district, a romantic 40-mile swath between Florence and Siena. Memorable sights include the historic 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 (five miles east of Radda); and majestic Castello di Brolio (10 miles southeast of Radda near San Regolo). Outside the Chianti Classico area lie Monteriggioni (described in Dante’s “Inferno”) and the wonderfully picturesque medieval city of San Gimignano. The Val d’Orcia wine region of southern Tuscany begins 45 minutes southeast of Siena, its vineyards producing celebrated reds such as the full-bodied Brunello di Montalcino and the refined Vino Nobile di Montepulciano.
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Hotel Borgo San FeliceEnchanting resort enclave set within a restored medieval hamlet, 30 minutes northeast of Siena. Mellow stone dwellings contain 43 simple but comfortable lodgings. |
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Hotel Le FontanelleWelcoming, understated 25-room hotel in handsome 13th-century brick-and-stone farmstead set on a hilltop overlooking miles of rolling countryside, eight miles east of Siena. |
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La ChiusaFamily-run manor that looks across to the hill town of Montepulciano. Fifteen lodgings are appointed with a mix of antique furnishings and modern amenities. |
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Borgo Santo PietroThirteenth-century stone farmhouse built as a resting place for pilgrims en route to Rome, converted to a lavish 15-room hotel (including six garden suites), 35 minutes southeast of Siena in a rural corner of Tuscany. |
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Castello del Nero Hotel & SpaFifty-room hilltop hotel constructed around an imposing 12th-century castle. Deluxe Rooms offer terra-cotta floors, vaulted ceilings, painted furniture and extra-spacious baths. |
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Hotel Certosa di MaggianoRomantic family-run hotel in a 14th-century monastery restored by the late architect and interior designer Renzo Mongiardino, amid serene gardens just outside of Siena. |
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Locanda dell'AmorosaPeaceful 27-room country inn fashioned from the remnants of a 14th-century stone hamlet amid vineyards and olive groves, 45 minutes east of Siena. |
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Relais Il FalconiereRelaxing country house hotel on a scenic hillside. The 22 guest quarters are divided between a 17th-century villa and a nearby manor. |
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Villa BordoniIntimate 10-room country house hotel in painstakingly restored Renaissance villa overlooking the vineyards, olive trees and forested hills of Chianti near the town of Greve, halfway between Florence and Siena. |
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Villa Il SognoA beautiful country road with pristine views leads up to the two-story villa situated on 3 acres of property. Fiesole |
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