This 50-room boutique hotel, designed by Alain Mertens (interior designer to Madonna and Sting), is another reinvention of the classic Tuscan villa. The 12th-century former nobleman’s residence on 990 hilly acres finds Philippe Starck Ghost chairs set beneath family crests and frescoes, and ancient stone-framed windows hung with bold curtains... More. Most of the rooms have wood-beamed ceilings, flat-screen TV’s, and marble bathrooms, not to mention stunning views of the property’s olive groves and vineyards. But be sure to venture out of your room for an aromatic massage at the spa or a meal of organic Tuscan dishes such as rice-and-spelt risotto served with porcini mushrooms and chestnuts at the hotel’s stable turned restaurant. Also on the estate: a historic, frescoed chapel and adjoining Florentine rose garden—ideal for reenacting scenes from your favorite E. M. Forster novel.

Address:
7 Strada Spicciano
Tavarnelle Val di Pesa
Italy

Phone:
39-055-806-470Less

In Montalcino, relax by the pool at Castello Banfi’s 14-room hotel in a 19th-century building restored to gorgeous effect by American Cristina Mariani-May, a co-CEO of the family winery. Enjoy the view from this hilltop hamlet nestled in Tuscany’s winery-filled Brunello region. The hotel offers weekend culinary classes taught by chef He... Moreinz Beck, from Rome’s Michelin three-starred La Pergola restaurant. Book the Federico Forquet-designed Double and Classic rooms—they’re a generous 432 and 540 square feet, respectively.

Address:
Poggio alle Mura
Montalcino
Italy

Phone:
39-0577-877-700Less

In 2002, transplanted Scottish restaurateurs David and Catherine Gardner discovered a ruin in Chianti and turned it into the wisteria-covered Villa Bordoni. The first-time hoteliers hired local interior designer Riccardo Barthel, who juxtaposed wood-paneled ceilings and antique bathroom tiles with witty touches like straw curtain tassels and a chic... Moreken-coop wall hanging. But it’s the whimsically decorated restaurant (frescoes feature thistles and vines) that’s the Gardners’ pride and joy. Chef Francesco Fineo reinterprets classic local ingredients—squab is paired with mashed celeriac and a grape-must reduction—while remaining true to traditional dishes such as bistecca alla fiorentina.

Address:
31-32 Via San Cresci
Greve in Chianti
Italy

Phone:
39-055-854-7453Less

This turreted villa has Art Nouveau touches and views of the Tyrrhenian Sea. Situated in the town of Castagneto Carducci, in Alta Maremma it holds a pitch-perfect mix of antique furnishings and neo-Baroque accents such as beaded lamps enlivens the seven fashionable rooms. Book one of the second-floor bedrooms which are slightly larger and overlook ... Moreforested hills and vineyards.

Address:
47 Via Umberto I
Castagneto Carducci
Italy

Phone:
39-0565-763-601Less

This hotel is for people who have been to Florence before and want to get to know the Chianti wine district outside it without sacrificing easy access to the city. Seven and a half miles separate Villa Mangiacane and the Tuscan capital, a distance the hotel invites guests to cover in a free shuttle. You can shoot down to Florence in the late aftern... Moreoon for some quick retail therapy and be back at Mangiacane in time for Negronis on the loggia, a sprawling, glamorous space with large-scale frescoes of hunting scenes and waist-high olive-oil jars from nearby Impruneta—but also lacquered Japanese stools, carved Balinese tables, and ottomans covered in zebra skin.

Address:
4 Via Faltignano
Florence
Italy

Phone:
39-055-829-0123Less

Close to the wine-producing village of Montepulciano, this 18th-century house is fresh from an eight-year restoration of its antiques-filled rooms. Outside, there’s a 1930’s swimming pool with Neoclassical fountains.

Address:
7 Via di Poggiano
Montepulciano
Italy

Phone:
39-... More0578-758-292Less