3 Best Hotels in Gaiole in Chianti, Tuscany

This centuries-old villa has old-fashioned guest rooms that are lovingly decorated with antique quilts and handmade wooden furnishings yet are also equipped with modern appliances. The owners are authorities on the surrounding area and happily draw maps and suggest wine-tasting and touring routes. Follow signs for San Marcellino Monti to get here.

Consisting of a former convent (dating from the 1300s) and a Romanesque church, this rustic yet elegant lodging has rooms with canopy beds, chiseled-stone fireplaces, and massage-jet tubs (in suites). Windows look out on the hills, woods, and vineyards. Dine by candlelight in the courtyard on sophisticated classics—carrè di agnello in crosta di noce (walnut-coated rack of lamb), for example—at the first-class restaurant.

An open-hearth fireplace and hand-hewn stone porticoes hark back to the 13th century, when this was a fortress, and although it's now a small hotel with modern amenities, including a beautiful outdoor pool, the traditional tone is maintained by the wood-beamed ceilings and simple, country-style furniture. The scent of lavender and rosemary wafts from the gardens, and all rooms have soothing views of the surrounding vineyards and hills.