For generations, designers have adopted towns, villages, and other enclaves as second homes and visited them again and again, imprinting a touch of their own sensibility on their chosen place—and importing something of its essence into their own work. It’s the kind of symbiosis that Coco Chanel and Le Corbusier, who summered in neighboring homes, enjoyed with the Cote d’Azur’s Rouquebrune Cap-Martine, or Yves Saint Laurent with Marrakech and Tangier. More recently, Christian Louboutin popularized the Portuguese village of Melides, eventually opening Vermelho Hotel there earlier this year. Here, five designers on the places they go, and why they continue to be pulled back.

Luke Edward Hall on Hydra, Greece

From Henry Miller to Leonard Cohen, bohemian creatives have long been seduced by Hydra’s austere, craggy mysteries. Such is its appeal for the English artist and designer Luke Edward Hall that he and his husband, Duncan, have returned to this tiny place in the Saronics every summer for six years—often tacking it on to a stop in Athens, where Hall is represented by The Breeder gallery. On Hydra, they sample various homes and villas and spend their days sunning, sleeping, and eating. Hall is never without his sketchbook. “A lot of my work is inspired by the Greco-Roman world, so I tap into that when I’m there,” he says. “You can imagine it in the ancient times and think about the mythology of the place.”

→ “I love buying things that are made on the island or nearby—sponges, soaps. One shop, Turquoise, sells block printed shirts and sandals—nice holiday kind of stuff.”

→ “The food on Hydra is delicious. We just want the same thing over and over again: loads of little things to share, like taramasalata and tzatziki. For lunch we’ll hop on a boat to this restaurant called Four Seasons. It’s not fancy, but it’s lovely. They have this amazing block of feta with honey and sesame seeds. We’ll also get squid or baked fish to share.”

→ “In the afternoon we might go see an exhibit at Deste Project Space Slaughterhouse, a slaughterhouse turned art gallery that had a Jeff Koons show last summer. Or we’ll work up the excitement to do a nice walk into the hills.”

As told to Betsy Blumenthal

Maria Cornejo on Santa Teresa, Costa Rica

For the veteran designer, whose Zero + Maria Cornejo brand celebrates its 25th anniversary this year, vacations are a much-needed chance to reset. “I’m the worst tourist,” says the New York–based, Chile-born fashion designer. “I just want to read, I want to walk, I don’t want to look at anything except nature.” That’s why, for over a decade, the pristine surf beaches of Santa Teresa, Costa Rica, have been a nearly annual getaway—a time to “clear her hard drive” with family and friends in between fashion seasons.

→ “I love waking up with the sun and going to sleep early. Some days I do 20,000 steps to the far end of the Santa Teresa beach and back. There are lots of rock pools and surf. It’s very lo-fi, there’s no scene, and I can just walk.”