Leanne Davis has always had a taste for wine. The California native runs her own winery, Via Romano Vineyards, outside Sacramento. So it's perhaps little surprise that her love of the grape is leading her to her next home: Tuscany, the lush enclave in central Italy famed for its vine-covered hills and bushy olive trees.

A decade ago, Davis and her husband, Jon Chewning, fell in love with the region when they were married by the mayor of Montepulciano, a romantic hilltop town about an hour and a half from Florence, the regional capital. Over the years, the couple returned, leading clients of their wine club on tours. They were so enchanted that, in 2022, they spent $32,000 on a home in Boccheggiano, a medieval town about two hours northeast of Florence.