One doesn't arrive in the Alentejo so much as decamp to it. The drive from Lisbon is short, less than an hour from the city center to the region’s northwestern edge, yet the sudden shift from busy capital to vast red earth is utterly transformative. Cross the Vasco da Gama Bridge over the mighty Tagus River, and, like that, all of the modern world is swept away, replaced by tiny villages and ancient castelos perched on humble hilltops. You almost get the sense that you’ve gone too far as you wind past millions of cork and olive trees, with only a bleating goat or sheep clad in jangling bells
to take notice of your presence.
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“Calma, calma” is the credo in this region, which makes up more than one-third of Portugal, yet is home to only 5 percent of the country’s population. Don’t stress, don’t worry, don’t rush if you don’t have to. The alentejanos, with their age-old customs and hospitable disposition, are still connected to their precious land, and here and there you’ll find their white herdades or montes—farmhouses—a welcome sight among the rolling scenery. These farms have maintained a sustainable agricultural system for generations, producing oil from the little-known Galega olive and wine from Alicante Bouschet, Trincadeira, and Antão Vaz grapes.
Recently, a few of these family homesteads have opened their doors to a new kind of trade—tourism—converting their century-old barns and crumbling ruins into charming country hotels for modern travelers. Some are the work of prodigal sons and daughters who left for careers in Lisbon only to return to their humble homes with a new business plan; others have been built by Portuguese natives who fell in love with the Alentejo’s simpler way of life. But despite the addition of sparkling pools, fine-dining restaurants, and world-class art collections, there isn’t a whiff of pomp to any of them. These rural retreats, spread across small villages throughout the region, are farms first, where cork and wild mushrooms have more status than frequent-flier miles or Instagram followers. The locals around here, both new and old, know well enough what mass tourism can do—they need only look to the Algarve for examples of what they don’t want their home to become—so they instead insist on indulging their guests in Alentejan authenticity. The luxuries are simple: time, space, tradition, and a hearty dose of calma.
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São Lourenço do Barrocal—Monsaraz
Like much of the Alentejo, there’s something wild about José António Uva’s estate. Unruly vines climb the white walls. Its roof tiles are bleached from centuries under the sun. Across the nearly 2,000 acres, thousand-year-old olive trees have grown gnarled and knotted.
This authenticity is by design, says Uva, who grew up there, just like seven generations of Uvas before him. In the early 2000s, he left behind an investment-banking career in Lisbon to return to his childhood home, hiring the Pritzker Prize–winning architect Eduardo Souto de Moura to transform its ancient stables and barns into a 40-room hotel. “What I aimed to do was make this a new home for a new community, without losing everything it represented throughout the centuries,” he says. It was no small feat. The project took 14 years, and the resulting rooms and cottages are carefully decorated with restored and custom art and design pieces, many sourced from the area.
Since day one, the hotel has maintained an organic farm. Plantations of almond and orange trees sit just beyond the pool, near rows of vines (whose grapes Uva’s family has been turning into fortified wines for more than a century) and overflowing rosemary bushes (whose flowers are used in the products at the hotel’s Susanne Kaufmann Spa). Still, guests come mostly for the wide-open spaces, to hike and ride on horseback through the hills of Monsaraz, and to live much like Uva’s ancestors did— only a little less wildly.
From $397
Herdade Da Malhadinha Nova—Albernoa
In the lower Alentejo, not far from the Algarve, this rural retreat with 200 acres of vines was first a winery, luring in-the-know travelers with its bright brancos and robust tintos. Then came the restaurant, overseen by chef Joachim Koerper of Lisbon’s Michelin-starred Eleven, and finally the hotel, which owners Rita and Paulo Soares have built amid a sprawling farm. The idea, says Rita, was not to update the old herdade, but to revert to it. “We feel so fortunate to have the privilege of preserving this land for the coming generations,” she says. “Going a little bit back in time, to our roots and our relationship with nature, is essential.” To that end, the Soareses collaborated with local craftspeople, most notably through the Algarve’s Tasa Project, an organization committed to reviving ancestral techniques and tools. The family has filled their property’s 30 rooms, suites, and villas with regional handicrafts, including terra-cotta vases, chairs woven from local bulrush, and linen cushions embroidered with the designs of old saddlebags.
The herdade also has its own coudelaria, a horse stable with 40 Lusitano horses, some trained for dressage, others ready for leisurely riding trips. After a ride through the property’s 1,100 acres—past oak groves, organic gardens, and dozens of beehives that produce more than 3,300 pounds of organic honey per year—settle in at the main house with a glass of Malhadinha Nova Tinto with views of the pool and miles of Alentejan hills beyond.
From $325
Dá Licença—Estremoz
The 300 acres of rolling hills on which this modern hotel stands once belonged to the nuns of the Convent of Estremoz, who, until the 1980s, cultivated an organic garden that produced some of the region’s best olive oil. Their 13,000 olive trees still stand today, as do the trio of 19th-century farmhouses where they lived and worked—though you’d hardly know it now that Vitor Borges and Franck Laigneau are running the place. Borges, a native of Portugal and former director of textiles and silk at Hermès, and Laigneau, a gallerist from Paris, happened upon the historic property while horseback riding, and, using their respective talents, have turned the estate into an art-filled hotel with five suites and three bedrooms. The pair named their property Dá Licença, which translates roughly to “with your permission,” a common greeting of respect among riders, and a reference to the regard for Alentejan tradition with which they approached the project.
Borges and Laigneau added new modernist structures to the old buildings and filled both with exquisite antiques—many of them from the late-19th-century Arts and Crafts movement— and custom furnishings from regional artisans, along with marble, ceramics, and countless pieces amassed throughout the couple’s world travels. Still, the pair’s very personal style doesn’t clash with its setting. “We love the relationship between the hotel and the pastoral surroundings—it’s all about connecting with the essence of the Alentejo,” Borges says. Since acquiring the property in 2015, the couple has prioritized the farm as much as the design; the estate is once again producing Galega olive oil and fresh herbs and vegetables from an organic garden.
The former olive mill is where the past and present collide most marvelously. There, Laigneau’s art—acquired over more than two decades and featuring mostly works from the Scandinavian Jugendstil and Rudolf Steiner’s Anthroposophical movements—is assembled in what the collector calls a “utopic gallery.” Hardly museum-like, the space is meant for reflection, where guests can embrace the Alentejo’s traditional yet sophisticated way of life.
From $347
Craveiral Farmhouse—São Teotónio
Live moves at a blissfully slow pace in the little fishing village of São Teotónio, where this unassuming country hotel sits near the picturesque shores of the Costa Vicentina. This is the calm seaside area of the Alentejo, a far cry from the busy beaches and all-inclusive hotels of the Algarve, and a draw for those with dreams of a simpler life. That includes Pedro Franca Pinto, the Lisbon-based lawyer who opened Craveiral two years ago, as much a refuge for himself as for others.
Pinto discovered the land for his hotel beneath a 22-acre field of carnations (cravo is the Portuguese word for the flower). The 38 suites and cottages are newly built, yet they easily blend in with the old farmhouses of São Teotónio, with their squat chimneys and tiled roofs. Inside, walls of cork and wood provide a modest backdrop for a handful of modern amenities, such as Hästens mattresses, soaking tubs, and minimalist furnishings from Portugal’s WeWood atelier. The mini-village also has four swimming pools and a wellness center.
But Pinto didn’t just want to be a hotelier—he wanted to be a farmer. “We planted over a thousand indigenous trees and tried to restore the land in an organic way—even the very local medronho [strawberry tree] has been planted throughout the property,” he says. He reserved almost two acres for a vegetable garden brimming with pumpkins, beets, lettuces, and tomatoes, and he made room for pygmy goats, black pigs, horses, donkeys, and chickens. The eggs are scrambled with sausage from a nearby butcher for breakfast. Come evening, the wood-burning oven is fired up to make pizzas, which are enjoyed with cool breezes that bring in the scent of olive trees and wildflowers from the coast.
From $173
