Like a good Tuscan meal, Borgo Finocchieto is meant to be shared. This 800-year-old farming village turned private dream retreat features five houses (with 22 rooms among them), arranged around a central piazza. The Borgo sits on six hilltop acres, with Instagram-worthy views of the valleys and towns beyond. Guests can take cooking classes in the instructional kitchen, join tastings in the impressive cellar, play tennis and bocce, or watch a movie in the screening room; there’s a ballroom and formal dining venue for destination weddings and other gatherings. Each meal is a celebration in itself.