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Seen from afar, the parish of Ponta do Sol looks as compact and picturesque as a postcard. Rippling green slopes of banana, palm, and pine fan out behind, houses dotted among the hills. All of this is surrounded by dramatic escarpment and made subtropically lush by the many small waterfalls that gurgle from the rock face, filling centuries-old irrigation canals.

Ponta do Sol is on the southern coast of Madeira, the main island of the Portuguese archipelago of the same name. The day after his long drive through the countryside, he approached the regional secretary of economy and asked point-blank: Why are you sleeping on digital nomads? Hall had long dreamed of finding a lifestyle where he could show up to work in flip-flops and shorts rather than the suits and ties of the bankers in his family. In early , the couple moved to Bali for two months, where Hall picked up his first remote contracts, including a marketing gig for a firm called Remote-how, and amassed a hefty contact list in the process.

Then they went to Thailand, Malaysia, Vietnam, and Bali again, spending a month or two in each before returning to Europe. Back in Lisbon, after less than a year of the digital nomad lifestyle, Hall was organizing conferences about remote work and digital nomadism, self-identifying as an expert on both.

When he landed in Madeira, he took in its low cost of living, fast internet speeds, surfable beaches , and Instagrammable beauty—the pillars of digital nomad marketing. He recognized something else as well in the pastoral pace.