Driving through Alentejo with my boyfriend, I kept coming back to the same thought: No wonder this has been kept a secret for so long! Followed by: Should I be keeping this to myself? Stretching from an hour’s drive south of Lisbon down to the tip of the Algarve and all the way out to Spain, Portugal's Alentejo region is vast but scantly populated, with empty roads opening up to sprawling landscapes by day and near-perfect views of the stars by night.

Home to some of the country's emptiest and prettiest beaches, endless vineyards, and hilly ancient villages, Alentejo offers an off-the-beaten-path serenity distinguishable from Portugal's better-known tourist destinations. You won’t spot tour buses or fast food chains for hundreds of kilometers; Selfie stick-yielding is seldom, if not a nonexistent phenomenon. And yet despite all of Alentejo's cultural offerings, one of the top things to do here remains, precisely, disconnecting and doing nothing besides taking it all in.

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Virtually every highway in Alentejo is dotted with olive groves.

In recent years, a handful of design hotels have popped up in the region, making Alentejo all the more alluring for aesthetes seeking a balance of nature and design. My boyfriend and I set out for a six-day road trip in early July, where we made stops in Motomor-O-Novo, Comporta, Monsaraz, Evora, and eventually Lisbon. We felt we had adequate time in each destination, although we happily would've stayed longer. Here, a design lover's guide on where to stay and what to do in the untapped region.

Where To Stay

L'And Vineyards

Lustrous decor and rural scenery converge with Michelin-starred dining at L’and Vineyards, a resort situated on the outskirts of Evora (the capital city of Alentejo) near the medieval ruins of Montemor-O-Novo. Designed by Brazilian architect Marico Kogan in 2011, the destination hotel has thoughtfully been arranged to be part of nature, rather than disrupting it. Low-slung white concrete buildings center around the property’s vineyard, set across a meticulously manicured landscape.

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Exterior shot of the main building at L’and Vineyards, which houses the property’s bar, lobby-lounge, Caudalie vinotherapy spa, indoor pool, and restaurant.

The design throughout L'and Vineyards is Scandinavian-like simplicity fused with Alentejo traditions through crisp-white walls, earthen textiles and woody midcentury furniture. And one ligneous masterpiece is more enviable than the next. Take, for example, the curvaceous George Nakashima bench opposite the lobby's fireplace, or the circle of chairs by architect John Serodio near the bar.

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A Sky suite at L’and Vineyards.

This distinguishable alchemy of nature and modern design extends into the property's guest dwellings. Each of the 25 guest rooms comes equipped with its own outdoor fireplace, seating area, and alfresco shower. Even more impressive are the 10 aptly named Sky suites, where bedrooms feature retractable roofs that allow guests to enjoy some of the world's best star-gazing conditions horizontally from bed. (Alentejo has virtually no light pollution.) The Sky suites have also been endowed with roomy private courtyard tubs, which are well worth the wait to fill up and experience.

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Despite opening up to a view of the property’s grounds, every terrace feels intimately secluded.

Rivaling the interiors at L'and Vineyards is the dining experience enjoyed in the property's restaurant—a lofty space with a sea of Tom Dixon light fixtures. The Michelin-starred restaurant with a tasting menu by Alentejo and Norwegian-trained chef José Miguel Tapadejo is not to be missed, as is the case with the complimentary wine and cheese tastings held daily in the bar lounge. LEARN MORE

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Nighttime view of the pool at L’and Vineyards and the stars.

Sublime Comporta

While Comporta is hardly under-the-radar (the hamlet has its own eponymous Assouline coffee table book), it remains a bohemian-chic destination akin to the Hamptons in the 1970s. The crown jewel of accommodations here is Sublime Comporta, a five-star resort situated a short drive away from three gorgeous beaches. Spanning 42 acres of cork trees, umbrella pines and pristine sand, the property features an award-winning spa, a garden with over 60 types of flowers and herbs, three restaurants, and standalone villas.

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Exterior shot of a villa at Sublime Comporta.

Earning its moniker, the design throughout the property is eco-chic minimalism. (Think earthy color palettes, floor-to-ceiling windows, rattan lamps, and whitewashed wood.) Coziness is also an integral part of the hotel's design DNA, as the property—built in 2004— was initially intended to be the family home of husband-and-wife owners Gonçalo and Patricia Pessoa. Recognizing that their creation was bigger than what they had imagined, the couple made the decision in 2014 to turn their home into a small rural country house. And so marked the gradual expansion of what's quickly turned into a favored jaunt of savvy, well-heeled travelers.

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The new bio-pool bungalow suites at Sublime Comporta.

Sublime Comporta currently offers 11 different room categories, ranging from standard rooms with queen-sized beds to five-bedroom cabana villas equipped their own private pools. The coolest new rooms to check into are the property's bungalow-style suites built on stilts above a bio-diverse pool—a touch that plays homage to fishing villages that have existed in the area for centuries. LEARN MORE

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A dining room inside one of Sublime Comporta’s Cabana villas.

What to See and Do

Peruse Art at Evora's Fundação Eugénio de Almeida

Get your cultural institution fix at Fundação Eugénio de Almeida, an eclectic contemporary art museum in Evora. Be sure to wonder through the maze-like corridors on the second floor to find a sun-filled room with enormous wooden ceilings and brilliant azulejo-tiled walls. The museum is located footsteps away from Templo di Diana, the city's most famous Roman Ruins, as well as a leafy park where an outdoor concessions stand serves the best sangria I've ever had for only 2.50 euros a glass. LEARN MORE

Explore the Village of Monsaraz

With a history that traces back to the pre-historical record, a half-day trip to the hilltop medieval village of Monsarez renders time travel. There's no shortage of idyllic landscape views from Monsarez, but be sure to peruse the walls of the village's castle, an addition to the village that dates back to 1310. For an air-conditioned break, pop into the Igreja de Santiago, a quietly tucked-away art gallery housed inside a church.

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Monsarez at dusk.

Situated just a stone's throw away from the Spanish border on the Rio Guadiana, the fortified village of whitewashed cottages is a 45-minute drive from Evora. (This is the seemingly universal distance of attractions in Alentejo). LEARN MORE

Pick Up a Tapestry Rug in Arraiolos

Located near Montemor-O-Novo and Evora, the small village of Arraiolos has been producing tapestry rugs inspired by Persian design since the 1600s. There's even a museum dedicated to the rugs in the village (that's housed within a former hospital), the Centro Interpretativo do Tapete de Arraiolos. LEARN MORE

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View of the village of Arraiolos.

See A Fishing Village in Carrasqueira

Fifteen minutes away from Comporta lies the authentically rustic fishing village of Carrasqueira, where fishermen are said to have lived and worked for over a thousand years. Easy bait for an Indie-skewing Instagram, visitors are able to walk on the dilapidated wooden beams and get a sense of what Comporta life was like before the hamlet came under the radar of jet-setting creatives like Christian Louboutin (a nearby homeowner) and Philippe Starck. LEARN MORE

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Jaimie Potters
We visited Carrasqueira at low-tide with ice creams purchased in the village in hand.

Shop Local in Comporta Village

Mom-and-pop shops brimming with locally sourced decorative objects line Comporta Village, making a short stroll here an absolute must. Find silky dresses and textiles from Central America at Manumaya, a store that pays homage to owner Manuela Gouveia's love and passion for Guatemala. Grab a smoothie or a light snack at the café adjacent to boutique Lavanda before heading inside to peruse ceramics, straw goods, and clothing from brands like Mason & Scotch. Finally, RICE is a concept store created by Portuguese interior designer Marta Mantero, which could alone validate checking an extra suitcase. You'll find bowls, decorative objects, jewelry, leather goods, furniture, and more—and the pricing is refreshingly reasonable.

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More to Consider

1. Plain and simple, a rental car is a must for exploring Alentejo. It will be nearly impossible to explore the region without one. (Also, if you're landing in Lisbon late at night, be sure to book a rental service that'll be open when you get into the airport as we noticed a few that were closed.)

2. For the adventurous, Parque Natural de Arrabida is a nearby area worth exploring, where windy roads lead to dramatic cliffside views of sparkling turquoise water. Less than an hour away from Lisbon's airport and only 90 minutes away from Comporta, you'll find swoon-worthy views and numerous beaches. If you're coming from Comporta, note that there's a scenic ferry that runs on the hour from Tróia Cais Sul to Setúbal, which is on the way to Parque Natural de Arrabida.

Portinho da Arrábida
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Photo of Portinho da Arrábida, one of the stunning beaches in the area.

3. Savvy, well-heeled travelers aren't the only group known to flock to Comporta in the summertime: Mosquitos are drawn to the area's famous rice fields. Just before sunset is the time of day you're most likely to encounter this minor annoyance. Note that Sublime Comporta does an amazing job at dealing with this, as the hotel is equipped with an endless supply of bug spray and has screens in all of the guest rooms.

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Jaimie Potters
Commerce Content Lead

Jaimie Potters is the Commerce Content Lead at Hearst. She also writes about fashion, interior design, travel, and more.