Perched high above the Bay of Positano, Il San Pietro is the epitome of Italian seaside glamour—the hotel has attracted a coterie of international VIPs since its opening in 1970, including Gregory Peck, George Clooney, and Julia Roberts—but retains the charm of a family-run inn. Michelin-starred Zass restaurant culls ingredients from the property’s organic gardens, which spill down to the sea across 10 terraces teeming with local produce, and rooms feature custom ceramic tiles made in local factories using traditional techniques. If the 400 steps down to Positano’s only private beach sound daunting, an elevator cuts through the rock to water level, where tangerine loungers on the stone sundeck give way to a cove with sandy shores. Here, breezy Carlino restaurant serves up lemon spaghetti beneath a cheerful thatched roof. Prefer more active endeavors? Hugging the cliff face above, seaside tennis courts serve up sets with a dazzling view.