Not Yet Trending is an investigative story from inside Airbnb. Tipped off by guest travel data, we find up-and-coming destinations before anyone else can. To get the story numbers can’t tell us, we go straight to the source: our hosts. Our latest discovery: a region of Portugal – in the middle of the Atlantic – where the islanders dwell in dormant volcanoes, the pineapples are the sweetest on the planet and, we discover, locals in the capital are fashioning their own hyper-creative downtown before your very eyes.

This shouldn’t be wine country – but it is. Not many people can say they built a vineyard from rock but Augusto Silva can. Refusing to be defeated by the unyielding, frozen-lava ground of his farm on the Azores island of Pico, he and his helpers, by cart or on their own backs, gathered soil from more fertile land further from the sea on this volcanic peak rearing above the mid-Atlantic.

To protect the grapes from the salt spray whipping in from the shoreline only a few hundred yards away, he crafted a nursery for each vine from the island’s porous black volcanic rock – walls of the kind that create a dramatic latticework right across Pico’s lowlands. Eighty now – he’s been farming on the Azores for 50 years – Augusto pours us a glass of the sweet, strong, amber wine that results from this tender horticulture. The secret to his longevity? “Work!” he says (and possibly wine, judging from the generosity with which he dispenses his homebrew from a battered old plastic bottle).

Augusto’s vinous creation is a tempting metaphor for the fecundity of the nine islands of the Azores as a whole – part of Portugal but long isolated, little known, yet in the past few years bubbling up with indigenous creativity that attracts and is inspired by independent-minded travellers.

In the arts, food, design and beyond, it’s often a younger generation of Azoreans with itchy feet who have left the islands to see the world only, inevitably, to return. “They bring richness with them from the outside,” says Cristina, who with her superhost husband, Robert, invites Airbnb guests to a traditional Azorean cottage on the largest island of São Miguel that they recently stripped of ill-advised 80s embellishments to expose its wood and limestone soul.

Of travellers’ recent rediscovery of the Azores, Cristina says, “It’s a little bit scary. I hope we follow the path of nature and sustainable, not mass, tourism. Nature is the most precious thing the islanders have.”

On the Azores, the face of nature stares back at you with equal beauty and force. The planet’s molten core is struggling to get out here, and it doesn’t mind whose footsies get in the way. Aptly named Furnas is a jade-green valley of unspeakable loveliness and rotten-egg stench arising from boiling rivulets of sulfurous grey mud. At a safe distance, cauldrons of the typical Azorean dish, cozida, a stew of chorizo, cabbage and sweet potatoes, bake for six hours in the soil. Ferraria is an ocean rockpool fed by hot springs – a natural spa where you can swim, transportingly, at night. And Fogo is a lake of sapphire blue that fills the funnel of a collapsed volcano.

In a similar locale to Fogo –  Sete Cidades, also on São Miguel – Airbnb host André has built lakeside lodges within a dormant crater that echo nature’s defiance of symmetry. When he first saw the dwellings’ unusual design, “I thought it was a mistake,” André says, yet the wonky roof angles and wood-clad sides of the structures lend them the subtlest of presences within this forest setting. Guests love the idea of living inside a volcano: it’s not violent eruptions that come to mind but rather, one says, “peace and beauty”.

As well as hosting, André grows the islands’ signature fruit – pineapples – in a few score greenhouses. It’s a labour-intensive, chemicals-free process that involves smoking the plants to bring out a sweetness and flavour that are a world away (almost literally) from the production-line species imprisoned on your average supermarket shelf.

Increasingly, the fertile but exposed landscape of the Azores – to the waves without, eruptions and tremors within – seems to be a foil to creative and productive endeavours such as André’s. Francisco takes Azorean seclusion to an extreme that will appeal to those who’ve always dreamed of being marooned on a paradise isle but would still like to be able to go into town occasionally to load some of the saliva-inducing pics they’ve shot on to Instagram. While the Azores are metaphorically off-grid, Francisco’s Airbnb studios are really off-grid: the fruit of a 20-year family building project, they’re located at the pointy end of a peninsula and rely on solar and wind turbines for power and natural springs for water.

“Check-in can take two hours,” Francisco explains, including pick-up from the nearest village, Ribeira Quente, and a jeep run with the luggage to the closest point you can get to on four wheels. The trek to your studio front door is probably worth it, though: there’s a wave-splashed swimming pool carved into the rock.

Still, “it’s not for everybody”, Francisco says – which for some of us will be exactly the point.

But hang on: this is the 21st century, after all. Haven’t the Azores got what everywhere else has: namely, cities? What you find is that the same spirit of indigenous but cosmopolitan creativity – the productive tension of looking both within and without that Cristina later calls “the islander’s duality” – courses as strongly through the cafés, clubs and back streets of the Azorean capital, Ponta Delgada, and the islands’ other urban locales.

“Even though we’re on the periphery on the Azores, we want to make a centre. We want to make the periphery the centre!” says Jesse James, co-creator of the islands’ annual Walk & Talk arts festival, from which the huge, fantastical murals emblazoned on the sides of many of the capital’s buildings were born.

It’s fascinating to watch that centre – like an embryonic Brooklyn, Shoreditch or Neuköln – taking shape. Two of its founding fathers are Mário Roberto and Vítor Marques: the latter coined the termO Quarteirão (‘the Quarter’) for a cluster of boutiques, galleries and eating places a few streets away from the more touristy zone near the port. With their assorted straw trilbies, baggy trousers and, in Vítor’s case, an apparently permanent cigarette, the two make rakish company as they show us around the burgeoning district.

Starting at the duo’s own photography gallery, Miolo, we pop in and out of the Azores’ sole vegetarian restaurant, popular Rotas; leather-goods shop Pele e Osso, selling rustic sandals inspired by the owner’s Azorean odysseys; eponymous fashion store Sara França, with bright dresses featuring local hortensia flower patterns; and Marota, offering reproduction vintage postcards of women in traditional capote, the shrouds they long wore on these still heavily Catholic islands.

With its evocative name (its former owner was a Paris fan), Louvre Michaelense is another trailblazing spot nearby that pretty much every creative type we spoke to name-checked as a place to hang out and sip um galão – a local latte – or two. Done up as an old-fashioned emporium with wood-panelling and floor-to-ceiling glass vitrines, it sells a vast miscellany of Azorean goods from needlework patterns to orange and passionfruit teas, tins of local tuna and jewellery made from old spoons and record vinyl.

They might be reviving a rundown neighbourhood but, Mário says, he and Vítor’s mission is clear: “We don’t want to blow up in a huge way. We want to be slow and world class. And we don’t want gentrification.” The fusty menswear stores and plastic-utensils specialists will hopefully stay, in other words, among the new hipster habitats.

The same inclusive sentiment reigns back on Pico at one of the islands’ standout architectural achievements of recent years, Cella Bar. Adapted from an austere old grey-stone portside wine warehouse, the drinks and eating spot has a sinuous wooden extension inspired by the wine barrels islanders used to float out to vessels waiting offshore.

“We spent six months thinking of screws!” says co-owner Filipe Paulo of a typical island delay in obtaining construction supplies. But the wait was worth it, with the building winning a prestigious international ArchDaily award, among others. Yet does this garlanded establishment signal ‘Keep out!’ to ordinary islanders who did without such a venue for so long?

Not at all, says Filipe. “It’s true in the summer we get mostly tourists, but in the winter locals hunker down here.”

Of course, no traveller can live on architecture alone. The Cella Bar’s limpets poached in butter and garlic lend a quiveringly sensual taste to this humble mollusc, and the ultra-fresh grilled octopus is so tender it feels somehow illicit. The Pico wines on offer, with their characteristic briny kick, wash the palate clear like fine Azorean surf.

“We deal with our shit,” says Joana of the presiding ethos behind her and husband Jaime’s Airbnb guesthouse, Quinta do Bom Despacho. To find out literally what she means, the deepest ecologists should head for some composting toilets at the back of the garden, but throughout her borderland domain seems to marry the hyperlocal, creative, sustainable spirit blooming in the Azores in both country and city.

Located just outside Ponta Delgada in a 17th century manorhouse with sweeping grounds, the property answers the motorway next door with an endemic garden and a natural swimming pond for guests where a squadron of frogs leap into the water as Joana skips along the perimeter – evidently her party trick. Another Azorean returnee, she traded a career “gallivanting” around the world as a sustainable-development consultant for charities such as Conservation International for “saving the world here”.

Guests can dwell upon relics of Joana’s grand Azorean lineage: a candelabra-like family tree sculpture, stern portraits of her ancestors that now lend a vintage vibe. Yet it’s the socially conscious approach that draws the crowds here: a rigorous ethical purchasing policy, a sensory garden with lemon verbena and curry plants for blind and wheelchair-bound locals, furniture made by the long-term unemployed. (Oh, and the posher rooms Joana shows us, one with a restored centuries-old four-poster, probably don’t hurt, either.)

Joana seems to embody a powerful new Azorean attitude when she says she’s seen the world and now she’s “happy for the world to come to me”.

A former FT Weekend columnist, Simon Busch writes on travel for Buzzfeed, the Independent and and broadcasts for the BBC World Service. He’s an Airbnb host in London.