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Winter, Not Summer, Is Prime in Puglia

This is Lesson No. 2: You may be in southern Italy, a mere ferry ride from Greece, but you will be cold. Puglia in the off-season is damp, rainy and bone-chillingly cold. But sitting fireside, sipping an Americano, it was easy to enjoy the slower, cozier side of the region.

If Acquarossa is about authenticity, then Casa Della Scrittrice is about living like a local. In fact, it’s like living with locals — ideal for experiencing that coziness. Francesco Pitrelli and his civil partner, David Capon, left their lives in London a few months ago, bought a trullo just outside of Ostuni, about 20 minutes inland from the coast, and opened a one-room bed-and-breakfast, complete with a pool, olive grove and very happy dog named Jack. “The winters are lovely because it’s so quiet here,” Mr. Capon said. “In the summer, you can barely walk through a piazza in Ostuni because there are so many people. And forget about parking.”

If, on the other hand, you’re looking for luxury and lots of it, try Borgo Egnazia, a masseria, or fortified farmhouse. The resort — consisting of a 63-room main building, a 92-room “village” of apartment buildings and 28 private villas — is a sprawl of giant, stacked white blocks, sitting right on the water. Pools (plural), a golf course, a bar scene worthy of South Beach, and bed linens with astronomically high thread counts — this is where you might go if you were a Hollywood celebrity, like, say, Justin Timberlake or Jessica Biel, who…

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