Seen from afar, the parish of Ponta do Sol looks as compact and picturesque as a postcard. There’s a small roundabout at the center, a gas station, a tiny shopping complex, and a cluster of modest buildings topped by terra-cotta roof tiles. 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. When Gonçalo Hall first drove through the area in September 2020, the words that came into his mind were: “What the fuck is this.”

Ponta do Sol is on the southern coast of Madeira, the main island of the Portuguese archipelago of the same name. Hall had visited Madeira once as a kid, but he didn’t remember it being so beautiful, so wild. Now, as he put it in an interview, he was seeing the place “with the eyes of a digital nomad.” He had returned to help run a conference about remote work in Madeira’s regional capital, Funchal. 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, 35, is tall and husky, with blond hair, blue eyes, a jovial demeanor, and a proclivity for speaking in hashtag mantras like “life is good” or “be happy, make millions.” He grew up in Lapa, the poshest area of Lisbon, but now keeps an apartment in Ponta do Sol with his wife, Catarina: Lisbon, he complained when we first met, had become too much of a melting pot. 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 2019, 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. A small nomad project that he had visited in rural Spain, just before his arrival in the archipelago, had impressed him; it was charming, more intimate than the bustling urban hubs he had experienced so far.

Established digital nomad hot spots, like Chiang Mai, Thailand, or Canggu, Bali, tend to be bubbles where wealthy and overwhelmingly white foreigners cluster at coffee shops, coworking spaces, and other businesses that cater to their wants and comforts in English. If he built a destination for digital nomads in small-town Madeira, Hall thought, things would be different. Itinerant remote workers could live just like locals, alongside locals: They could reside in the same neighborhoods, eat at the same restaurants, and mingle at gatherings coordinated by a “community manager.” Hall decided to pitch his idea to the Madeiran government.

It was an easy sell. Tourism in the archipelago had plummeted due to the Covid-19 travel bans that had barred travelers from outside of Europe’s Schengen Area, and so Hall framed digital nomads as the cure. Portugal’s urban centers were already saturated with remote workers, but Madeira, less than a two-hour flight from Lisbon, was still under the radar. High-earning professionals could pour money into local businesses, Hall told regional officials. All they needed to welcome them was an inviting infrastructure and a ready-made network to land in. If he built it, Hall promised, they would come. 

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