La Bandita, Pienza
Tuscany’s chicest and friendliest country hotel is also a perfect rental property. Run by former music executive John Voigtmann, La Bandita features seven rooms in a gracefully modernized farmhouse and one stand-alone suite in the converted pigsty next door. The interiors put Tuscan materials, like terracotta, to contemporary use in rooms that are minimalist without being cold. Voigtmann is an affable host, and his in-depth knowledge of Tuscan wine comes through not only in La Bandita’s well-stocked cellar but also in weekly Brunello tastings—when leading local producers like Andrea Franchetti sometimes drop by for dinner with a couple of special bottles. Private tours of cult wineries like Sesti or Cerbaiona can be arranged, and talented house chef David Mangan organizes pairings of, for example, wine and truffles. Rentals start at $19,700 per week (sleeps 16); la-bandita.com.