From Rome, head south along the coast to one of Italy’s most celebrated destination: the coastal town of Positano. You can take a day to hike into the coastal hills via a stone stairway to Montepertuso, which literally means “hole in the mountain.” That’s because the picturesque town sits within hiking distance of a dramatic rock wall with a hole through the middle, complete with a local legend about its creation during a fight between the Virgin Mary and the Devil. After a hearty trek into the mountains and back, Judy recommends staying at Le Sirenuse. The hotel is practically an attraction unto itself in Positano, with commanding views overlooking the sea, and impeccable service, from the Michelin-starred chef at Ristorante la Sponda to the sumptuous spa where you can stop in for treatments to relax well-worked muscles.
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