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Experience Italy's most glamorous island during the off-season

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June, July, August? No," says the concierge. "You go in May, September, October. You come now? Perfetto." We're sitting on a cushioned chaise longue at J.K. Place Capri, a boutique hotel on the island of Capri that overlooks the Tyrrhenian Sea. It's a perfect sunny day, with a few clouds drifting over the summit of Mount Vesuvius, and I am receiving a crash course in Capri sightseeing from a gentleman who has worked in hotels all around the world, from Sorrento, Italy, to Sydney to San Francisco.

And he's right, of course, about June, July and August. The weather is gorgeous, yes, but the crowds! Huge flocks of people from all over the world descend on this Italian island, their cameras at the ready. Their tourism dollars keep the economy thriving, but the tourists also make it difficult to really see a place if, like me, one prefers peace, quiet and short queues. So I flew to Italy from New York in mid-October 2013, after many of the restaurants and hotels had already closed for the season and the temperature had dipped to a balmy 75 degrees Fahrenheit. I booked a guest room with a view of the Tyrrhenian at J.K. Place Capri and got busy doing nothing. My travel companions and I were not alone, though. The island is never really empty, and all manner of travelers still dotted the streets. But the vibe was that of a beach town in late fall: calm, relaxed, luxuriously under the radar and definitely worth skipping a few days of school or work to experience.

Traveling to Italy in the off-season is a funny thing. One can go for days on end without speaking to a soul (beyond the usual "Grazie mille") and then, out of the blue, make new friends and find oneself awake and full of wine late at night, playing charades by the light of a full moon. J.K. Place Capri's homey design inspired a feeling of comfort and conviviality; at every turn, a new book or flower or piece of art surprised me. Stacks of monographs, autobiographies, tarot guides and travelogues invited me to stop in my tracks, sink into an overstuffed sofa and let my mind wander. A balmy breeze blew in through French doors that never closed, beckoning me to go outside.

Effortless adventure is the whole point of Capri

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That mix of serenity and effortless adventure is the whole point of Capri. Each morning, my companions and I took our cappuccinos and croissants outdoors. We sat by the pool in the private courtyard and watched sunbathers lie on the public beach below, their towels spread out on the sand. Each afternoon at four o'clock, we gathered again on the wraparound deck to retell the day's stories and drink fresh, crisp wine. In the hours between, there was an entire island to explore by foot, boat and convertible taxi.

Though the concierge insisted it could not be done in a day, I ran from one end of Capri to the other—up a rambling wooded path to a 1st-century Roman villa, through the maze of streets in town and up, up, up all 800 Scala Fenicia ("Phoenician steps" in English), a stone staircase that once served as the only link between Capri and its rustic neighbor, Anacapri. My companions and I rode a rickety chairlift to the top of Anacapri's Mount Solaro and looked out to sea as far as we could—to Tunisia, perhaps, or somewhere even farther off. As we hiked back down the hillside, we followed no road and let ourselves get lost on footpaths barely visible through tangles of grass. We paused atop a deserted bluff and listened, but there were no voices, no traffic for miles, just us and the bees and the golden light of an autumn afternoon.

One can't do that during the high season. There aren't many places to disappear to for an hour, where one can wander back to a familiar road—familiar after just one day—and find one's way back to town. Eventually, we, too, found our way, which we always did, just in time for cocktail hour. And thus our days in Capri passed.

Enrique one of the Top 10 Best New Chefs

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I'm relaxing on the colorful patio at Jose Enrique's namesake restaurant, tucked away from the buzzing streets of San Juan, Puerto Rico. A ceiling fan swirls in the heavy heat. My reverie is interrupted when a server pops open a bottle of Billecart-Salmon brut rosé and pours it into a frosted flute.

Enrique emerges from the kitchen carrying a mahimahi ceviche made with bits of passion fruit, mango, tomato and plantain chips. It's superbly fresh and tangy. "I like to use fish that's fresh off the boat," says the chef (though he'd rather be addressed simply as a cook), who is sporting a three-day-old beard, nerdy glasses and a black T-shirt emblazoned with a psychedelic print. Every day he roams the nearby mercado for fresh ingredients in order to create his daily menu, which is inspired by his finds and, more important, his mood.

Food & Wine magazine voted Enrique one of the Top 10 Best New Chefs of 2013, and he is just one of a new generation of Puerto Ricans—artists, restaurateurs and hoteliers—who are shaking up the tiny island mostly known for its low-key beaches populated by surfers. This new crowd is mixing international trends with local traditions and infusing a vibrant energy into all of Puerto Rico but more specifically into its capital, San Juan. In addition to fine restaurants, a cluster of art galleries and cultural centers has emerged, grouped in the capital city's neighborhoods of Old San Juan and hip Santurce. And for those seeking a lavish retreat after an immersion in San Juan's creative atmosphere, such luxury resorts as the Dorado Beach, a Ritz-Carlton Reserve; the St. Regis Bahia Beach Resort; and the Royal Isabela golf resort recently opened and are combining elegance and nature in the heart of the island.

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