Castello Banfi Il BorgoOne of region’s largest wine estates, Banfi’s Montalcino property includes a magnificent hilltop castle-fortress, Poggio alle Mura, which first appeared in regional documents in 1318. The castle now houses the winery’s tasting room and restaurant, and the stone homes that made up the workers’ village in the 1700s have been converted into a 14-room hotel. Beamed ceilings and stone archways prevail in the country-chic lodgings, which offer scenic views over 7,000 acres of hillside vineyards. From $484/night; castellobanfiilborgo.com

Monteverdi, Castiglioncello del TrinoroThe town of Castiglioncello del Trinoro, set high on a hill in the Val d’Orcia, comprises three grand villas in which centuries-old stone walls and wood beams play off modern decor by Rome-based designer Ilaria Miani. Stroll down medieval stone lanes to reach the cozy enoteca, head to the hilltop pool to soak up the incredible views, or listen to classical music at the 14th-century church. From $618/night; monteverdituscany.com

Villa Machiavelli, San Casciano Val di PesaThe former home of the Machiavelli family (including that Machiavelli), designed by none other than Michelangelo, this 15th-century estate sits on 600 acres of vineyards just 20 minutes south of Florence. The staffed villa features ten bedrooms, an elegant drawing room, a full kitchen, and a stone wine cellar with a long table ideal for family-style dinners served with wine from the estate. From $52,852/week; akvillas.com

This neoclassical villa was built in the 1700s by Swiss architect Felice Soave and decorated by Giocondo Albertolli, who also did Florence’s Uffizi Gallery. The nine-suite property features a public room with frescoes and carved marble accents and gardens complete with a heated swimming pool. Famous guests include composer Vincenzo Bellini (who wrote his opera Norma here), Winston Churchill, and Napoléon Bonaparte. From $39,354/week; thevillapassalacqua.com

Aman VeniceThe Aman brand gets downright opulent at this 24-room hotel, set inside the 16th-century Palazzo Papadopoli on the Grand Canal in Venice. Inside is a study in contrasts by designer Jean-Michel Gathy, with Aman’s signature minimalist furnishings paired with silk wall coverings, gilt rococo reliefs, and historic frescoes by Renaissance master Giovanni Battista Tiepolo. Outside, a private garden and hidden jetty keep it paparazzi-proof, no doubt part of the appeal for George and Amal Clooney, who tied the knot here in 2014. From $1,068/night; aman.com

Castello del Nero Hotel & Spa, Tavarnelle Val di PesaSituated midway between Florence and Siena in Tuscany, this luxe 50-room hotel was created from a 12th-century castle and a series of 15th-to-17th-century villas. A museum-quality restoration of the frescoed walls, beamed ceilings, and terra-cotta floors was supervised by the Italian Fine Art Commission. Take the complimentary shuttles into Florence and Siena for more arts, or just stay on-site and indulge at the Espa spa (the largest in Italy) or Michelin-starred restaurant La Torre. From $483/night; castellodelnero.com

Villa Cora, FlorenceNext door to Florence’s acclaimed Boboli Gardens, Villa Cora was built in the 1860 by Baron Gustave Oppenheimer as a gift for his wife. It’s worth a visit alone to see the public halls, especially the Baroque Hall of Mirrors—one of Florence’s most coveted event rooms, decorated with elaborate frescoes and opulent gilt details at every turn. Tchaikovsky stayed here, and you can too, in one of 46 rooms and suites gorgeously appointed with canopy beds and Carrara marble. The property, a member of Relais & Châteaux, is also home to Florence’s only outdoor heated pool. From $334/night; villacora.it