Hotel La Collegiata, San Gimignano, Tuscany, Italy
This place is textbook Tuscany, and one of the prettiest properties in the entire region. In its past lives it's been a 16th-century Capuchin monastery, and the summer residence of the noble Guicciardini-Strozzi family: so expect historic stone buildings, fabulous formal gardens, grand rooms (kept spotlessly clean) with traditionally Tuscan tints, and food and wine that remains loyal to the locale.
Wine-tastings and cellar tours, in-room massages, and a peacefully pristine pool round-out the full sensory experience.