If you have a car, consider visiting Assisi from smaller nearby towns, like the appealing wine village of Montefalco, about 20 minutes south. This old estate, in the Zuccari family since the 16th century, will make you feel like a guest in a gracious Italian home. (You’ll also be within easy reach of Spello, Trevi, Spoleto, Todi, and other Umbrian hill towns.) Airy, light-filled bedrooms are large and comfortably equipped with armchairs, king-size beds, nice antiques, and big marble-sheathed bathrooms. Palm-shaded gardens surrounding the pool invite guests to linger, and welcoming lounges are filled with books and pottery. Dinners are served in a vaulted room glistening with terracotta tiles.

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