"Montalcino The location: Montalcino, a hilltop town famed for its production of Brunello di Montalcino wine, made from the town's sangiovese grosso grapes—it's an hour and a half by car from Florence and 45 minutes by car from Siena Top amenities: On-site Brunello di Montalcino winery, 18-hole golf course, cooking classes, spa, infinity pool, truffle-hunting outings We've already listed the terrific amenities—which, yes, include truffle hunting—but if you need more information on Rosewood Castiglion del Bosco, we'll go on. This Tuscan estate is on 5,000 acres and has 42 suites and 11 villas. Travel reporter and Condé Nast Traveler contributor Laura Itzkowitz—who lived in Rome previously and writes often about Italy—describes the bedrooms as “lavish” in her hotel review for the magazine: “If money were no object,” she writes, “I would check into one of the sumptuous villas and never leave. Each one comes with a private heated pool, though some feature woodburning pizza ovens, a home theater, or tennis court.”" - Alex Erdekian
