Minutes later, knobby, footed glasses of madeira—the storied fortified wine that shares a name with the island its grapes are grown on—arrive at the table, along with the bottles they were poured from, each dated in white paint, by hand.

This game goes on for four rounds, starting with sercial, the lightest and driest (though still delicately sweet) style of madeira. We make our way along the sweetness spectrum, moving to medium-dry verdelho, then medium-sweet bual, ending with malvasia on the darker, more confectionery side. Each flight offers bottles older than the last. The oldest we taste, 1907, was born four years before my grandmother. But it’s the verdelhos—1994, 1973, 1932, and 1912—that have my attention. The youngest one smells like fresh tropical fruit, brown sugar, and toffee, while the oldest, the dark color of chestnut skin, has moved into a place of earthiness and fig pudding, with a liveliness that I can’t reconcile with its age.

On Madeira, we’re far away from the admired crus of Burgundy and the fogged-in hills of Piedmont. Closer to Morocco than its mother Portugal, the island is actually the tippy top of a long-extinct volcano in the middle of the Atlantic, where the D’Oliveira family has been making the island’s namesake wine since 1850. Today, Filipe, Luis’ nephew, the sixth generation, is the winemaker. “We have a particular situation that’s different from other producers of Madeira,” D’Oliveira tells me. “The winemaker is always part of our family. We always have the same style because we learn from other generations.” I can taste this through-line in the wines.

This 306-square-mile hunk of extremely lush, craggy molten rock sits on its own, exposed, save for a few teenier islets that make up a largely unpopulated subtropical archipelago. Here, minuscule vineyard plots commingle with palms and banana trees, sugarcane, and umpteen varieties of succulents that fill every crack of every blunt stone wall. The volcanic soil is exceptionally fertile, giving way to at least 15 types of passion fruit, thick, sweet annona (custard apples), and the creamiest sweet potatoes.

I’ve been to many wine regions, but I’ve never seen a banana tree in one before. Somehow, for the past several hundred years, Madeira has balanced its roles as being a storied wine producer—world-renowned for its fortified wine that’s unmatched in ageability—and a warm-weather escape for mostly northern Europeans looking to whale-watch, sunbathe, and hike its forested mountains.

Most Americans don’t know that Madeira (pronounced ma-DIE-ra in Portuguese; we’ve been wrong all these years) is a Portuguese island, and if they have heard of the wine, they often believe that it is a version of port. But the wine is stand-alone in its recipe and production. In the 500-plus years that madeira has been produced, it has inspired plenty of cerebral dalliances, for walking a line between the subtle and the outrageous, its dark cellars in the tropics, and its ability to last longer than any of us will. But it’s also infinitely satisfying in all the ways the palate wants: sweet and densely soothing, with a spine of acidity that calls us to finish the glass. On madeira, a grapevine can produce 8 kilograms of fruit (in other wine regions, it’s closer to 3). Here, the vines are cultivated for maximum production largely because land space is tight—and growers are paid by weight. There are around 3,000 grape growers on Madeira (who, on average, tend to around one-third of an acre of vines), who sell to the eight producers of madeira that remain on the island. Most buy from at least 100 growers. Vines are grown on tall pergolas to allow good airflow, necessary in the summer’s heat and humidity. The majority of vineyards, concentrated along the coasts, are planted with the red tinta negra grape, but certain areas are best for the coveted white grapes that give the different varieties their name: sercial, verdelho, bual, and malvasia. That this place would produce unparalleled bottles is hard enough to fathom, but the process used to make the wines is divergent too: They’re not only fortified—in which a neutral grape spirit is added after fermentation to prolong the shelf life—they’re also intentionally heated and oxidized, both processes that most winemakers vehemently avoid. The best madeiras are left to age in-barrel for 20-plus years.

In D’Oliveira’s case, a good amount of the wines that were made by his family in 1850 are still kicking around in barrels, morphing, deepening, finding themselves, waiting to be ready in the temporal sense of the word. The wines are made with the understanding that it might be a future generation that sees them through to completion. This spring, the 1988 bual was released for the first time.

The only trouble with keeping so many old vintages around is that the barrels—well-aged American oak, painted with red rims—take up a lot of room. In 2017, the winery couldn’t produce as much madeira as usual; despite owning five storage warehouses around the capital city of Funchal, they’d maxed out on space, with 5 million liters of wine.

Madeira, the island, is on the way to exactly nowhere, and yet it served as an important pit stop along the spice route from India to the Americas—a navigational star for sailors who took with them wine that had been fortified to give it durability on its long journey. (The barrel aging and heating today mimics the wine’s time spent aboard those ships.) Madeira’s history is long and bizarrely tied to world history, including the early days of the U.S., when Thomas Jefferson, a serious madeira enthusiast, arranged it so that cups were filled with the wine at the signing of the Declaration of Independence. Perhaps this is how madeira earned its fusty smoking-jacket reputation. But as I stood on a cliff, eating a red, finger-shaped passion fruit at a roadside stand outside São Jorge, overlooking the crashing sea and ­terra-cotta-roofed houses in butter pink and salmon orange in the towns of Boaventura and São Vicente below, it seemed far from fusty.

Although in the States sommeliers endeavor to pair these wines with every course of a meal (their incredible acidity makes it possible to even serve sweeter wine with meat courses), this isn't the case on-island. "In Madeira, people only drink madeira for special occasions, but I think this is OK, so we have enough for export," D'Oliveira says with a smile. "It's the same thing they say about scotch." While madeira isn't found regularly on dinner tables on the island, bual madeira is the variety that tends to be drunk at social gatherings and celebrations. Most people drink Coral, the local lager, or ­poncha, a sort of sweet rum punch often made with honey, which go better with the fresh seafood and warm weather.

On my way out the door, D'Oliveira hands me a paper-wrapped bolo de mel, a spice cake made with sugarcane syrup from the island. He tells me this signature cake is about the only food a Madeiran will eat with madeira—preferably with an ultrasweet malvasia. It was the first of these little parcels I would come to see everywhere on my visit.

When I get out of the car at Barbeito, in the hills above Câmara de Lobos—a fishing village composed in primary colors, like a salty box of crayons—I am nearly blown from the cliff. I’d arrived on Madeira the day after a monster of a storm had hit the “always summer” island. And in my five days there, I witnessed hail at a 45-degree angle on the north coast skirting VE-1 highway, full-arc rainbows, mini avalanches that effectively closed roads, Câmara de Lobos with all of its boats yanked from the water, and the remnants of 40-foot waves crashing in the surf town of Jardim do Mar. The highway from Funchal to Barbeito follows the coast, a series of winding curves and tunnels carved into the mountain that is Madeira. Until Portugal joined the EU, the only roads on the island were one-lane local routes that cut through its center, which meant that getting from one place to the next involved steep inclines and blind corners. The island is far more navigable now, making it possible to drive the entire circumference, with stops along the way, in a day.

Up here at 2,000 feet, the wind is swirling a fine mist through the guts of Ricardo Freitas’ winery, which sits out in the open air. “Madeira doesn’t get hurt with hot or cold temperatures,” he tells me as we walk through a row of towering stainless-steel tanks. If D’Oliveira is a traditionalist, Freitas is a modernist, but one endeavoring to make traditional wines. He’s respected among other producers for pushing the envelope.

Freitas pours me a sample of his work in progress, and it's not madeira. It's a completely dry still white wine (a novelty on this sweet-centric island), made from the verdelho grape, his first vintage. The young wine is pale yellow and tart, like biting into a crisp Granny Smith apple. It's exactly what I would have wanted with my garlicky limpets (local sea snails often served grilled in their shells) and espada (startlingly ugly, but tasty, black scabbard fish) the night before. Perhaps this would be more welcome among the locals, I think to myself.

Freitas tells me that he makes madeira more like a dry table wine than a sweet fortified one, working in small batches from specific vineyard plots, blending just before bottling. Because all of the madeira houses source grapes from all over, madeira has always been less about the base ingredient or the terroir than what happens to the grapes in the cellar. Freitas is hoping to change this, putting more emphasis on the quality of the grapes and how they’re grown. He’s even working on some single-vineyard bottlings. Whereas many madeira producers will add sugar to hit the right concentration just before bottling, Freitas uses fortification as a means of stopping fermentation, controlling the sugar content so there’s no last-minute correction necessary.

He shows me more of his gear, a small lagar where a tiny portion of his grapes are stomped by foot, a high-tech basket press that's as gentle as presses from 100 years ago. He shows me the control panel for the estufagem, the tanks in which his three- and five-year-old blended madeiras are heated to 115 to 120 degrees for months at a time, a means of concentrating the wines relatively swiftly; as the water evaporates, the wines become richer and fuller. Vintage wines never see the inside of an estufagem. After fortification, they go straight into old barrels strategically placed in the cellar to warm up naturally. By law, vintage madeiras that stay in-barrel for more than 20 years are called frasqueira wines; those aged five or more years are colheita wines.

In an unguarded moment, Freitas tells me about his grandfather, the person who taught him how to make wine. “He had a huge library, 25,000 books,” most of which were lost in a devastating flood in 2010. “He had the biggest collection of books on Christopher Columbus in Europe. They say Columbus was here in Madeira studying sea currents.” Apparently, Columbus’ wife was from Madeira. Perhaps the wine was in America even earlier than we think.

Freitas continues to work with a number of growers who used to sell grapes to his grandfather. In a small place, these relationships are ever more important. He’s collaborating on several projects with old friends, enabling him to work with some of Madeira’s more storied sites. One such project is with a farm called Fajã dos Padres that everyone I meet speaks of as the gem of the island. The sea-level property is accessible only by cable car or speedboat, assuredly guided by schools of dolphins and whales, the steeds of Poseidon. The Fajã’s history goes back to the 19th century when some Jesuit priests owned the land there, farming grapes and other produce. When phylloxera (a nasty, vine-ending bug) infected the island, destroying the vineyards, the Jesuits jumped ship. Over the years, various people have occupied the land, but it was the current owners who discovered the one remaining vine of a grape called Malvasia candida; they propagated it and now have the only vineyard plot of this grape in Madeira. Today, the site has an organic garden and restaurant that tourists can visit, but it’s Freitas who has been helping out with bottling the madeira from the site. His first bottling was the 1986, which he bottled in 2012. “I stayed with that wine for seven years in the winery before bottling it,” he tells me. The wine is very sweet, curried, nutmeg-spiced.

All the winemaking happens in Funchal, but to experience the island itself, you have to leave the city. There’s no wrong direction—you can lap the island in a day

“This is the new world, the center of the winery where I make small blends, the final steps of winemaking. Everything comes to the center,” Freitas says as we walk into his 10-year-old cellar. Everything about the warehouse has been engineered to make it the ideal place to store old barrels of madeira. The roof is made of a thin metal, with rounded corners to draw heat into the room, while the corners at floor-level are reinforced with concrete for maximum coolness. The walls are lined in windows to be opened in the summer, to allow in the island’s typical 70-degree heat and humid breeze. Freitas takes a small sample from every barrel four times per year, tasting each one to check in. Every cask is mapped out on an Excel sheet so he always knows what’s going on in every one, each its own universe.

With all of these calibrations, the wines could come off as overly fussed with, but when we sit to taste, they just aren’t. Freitas first pulls a couple of 2011 vintage component wines (wines meant for blending) and 1967 tinta negras for a blend that he’s working on. We taste them on their own, then in combination. By adding 10 percent of the 1967 to the 2011, he creates a wine that is fuller, with marmalade and toast notes, caramel apple, and a pointed citrus edge. He’s still not satisfied.

We taste through dozens of Freitas’ wines, including a verdelho from my birth year, 1981, which was just bottled in early 2017. The wine is more overtly powerful than many of the medium-dry verdelhos I’ve tasted, with a coffeelike bitterness matched by the smoothness of maple syrup slinking off the back of a spoon. But the standout of the tasting is a 50-year-old blend that Freitas named for his grandfather, Avo Mario, based on the rare red bastardo grape, with just 3 percent of tinta negra from 1954. The wine is lifted and direct, with caramelized sugars and flavors that remind me of crystallized dates and candied orange peel.

We sit down for lunch at a nearby restaurant, Santo Antonio, which looks down toward the fishing cove of Câmara de Lobos. First to arrive on the table here—and in every restaurant I dine in on-island—is bolo de caco, a pita-size loaf of puffy bread, an inch or two thick, that’s been sliced into two hemispheres and slathered with garlic butter in the center. Garlic is a recurring flavor in dishes on Madeira, and bolo de caco is standard with every meal. Next arrives espetadas—enormous bay-leaf-scented skewers, a few feet long, strung with baseball-size cubes of beef that are roasted in a wood-fired oven and then hung on hooks over the center of the table. Freitas demonstrates how to pull a piece of beef off the wide rod one piece at a time. Espetada is also found in every restaurant on the island, which strikes me as bizarre, since the island is too small and steep for raising cattle; it’s all imported. The beef left behind on the skewers stays warm by contact with the rod. On the side is milho frito, fried cubes of smooth, herbed polenta, along with fried potatoes, the patron saint of vegetables in Madeira. Outside the winds whip up the hills from the coast, rattling through banana leaves.

And there is no madeira in sight.

1. Justino's
Winemaker Juan Teixeira works with 800 growers, spread over the island, who help make it the largest producer on Madeira, with 4,000 barrels currently.

2. Barbeito
Founded with unwanted stocks of old vintages in the '40s, today, the company's wines, and its collaborations with Rare Wine Co., are worth seeking out.

3. D'Oliveira
This sixth-­generation producer's bottles are easy to find in the old town area of Funchal—some even dating back as early as the 1850s.

4. Madeira Vintners
A new madeira company is virtually unheard of, but Madeira Vintners is only in its fifth year and is run entirely by women, including its winemaker.

5. Blandy's
Francisco Albuquer-que has been the winemaker since '89. But this company has stocks from as far back as the mid-19th century in its basement cellar.