A road trip from Lisbon along the Vicentine and Algarve coasts reveals the natural drama of the region while uncovering some of the country’s most exciting new hotels and restaurants.

*Left to right:* Spaghetti alle vongole at Rocco; the restaurant’s retro-chic interior. (Courtesy of Rocco)

I would hate for life to be boring,” says Gail Curley, co-owner of Lisbon’s Palácio Príncipe Real (doubles from US$430). And this pink-walled 19th-century palace that she and her husband have recently transformed into a playfully pretty boutique hotel is anything but. Stepping through the hidden doorway into an oasis of jacaranda and lemon trees inset with a pool, I feel as though I’ve tumbled down Alice’s rabbit hole. Outside the high walls, wooden trams clatter along cobbled streets lined with striking tiled buildings. I half expect to see a peacock strut past, so lush are the grounds.

Indeed, Curley wanted guests to feel a frisson of surprise when checking in to one of the 28 rooms here, each individually designed with open fireplaces, freestanding baths, and large balconies with views toward the Tagus River. There’s also a lovely guests-only restaurant, though for tonight’s dinner I have snagged a seat at the hottest table in town: Rocco, set within the even newer Ivens hotel in nearby Chiado. The decor here is decadent, all floral prints and polished marble. The food, meanwhile, is part Italian, part Portuguese: think lobster with garlic butter and saffron risotto, truffled steak tartare, and brown crab ravioli.

The Tagus remains my backdrop the next day as I drive 30 minutes west to Estoril, stopping briefly in the seaside neighborhood of Belém to sample a pastel de nata tart from the original purveyor, sixth-generation family-run pastelaria Pastéis de Belém. The pastry is just the right amount of crunchy, the egg-yolk custard delectably sweet and smooth. It’s still warm from the oven, as you’d expect from a place that turns out thousands of these delicacies daily.

At my hotel for the night, Estoril Vintage (doubles from US$340), the manager informs me that the surrounding resort town is one of the most salubrious—and expensive—places to live on the Iberian Peninsula. Proximity to Lisbon aside, residents enjoy sweeping views of the Atlantic Ocean. There’s dappled sunlight and a long swath of sand, and elaborate mansions (like the one occupied by this hotel) that nod to the region’s riches.

I wander down Estoril Vintage’s ornate central staircase to the dining room, where dapper waiters serve sopa de peixe (a thick fish soup), oven-roasted octopus, and juicy shrimp with eggplant caviar. It’s a meal worthy of the region’s elegant heritage, and it keeps me fueled for the detour north to Sintra the next morning.

*Left to right:* Views of the Cascais waterfront from the lawn at Estoril Vintage; one of the hotel’s 18 guest rooms. (Photos: Salvador Colaço)

*Left to right:* Queuing for egg tarts at Pastéis de Belém; the Arriba Fóssil da Galé cliffs in Melides. (Photos: Natasha Dragun)

It is said that the palaces in Sintra were inspired by Bavaria’s Neuschwanstein Castle. The most elaborate, Palácio da Pena, is a pastel-hued confection of cupolas, turrets, gargoyles, and ramparts. Arguably the best view of this 19th-century extravaganza is from the nearby Castle of the Moors, whose ancient granite walls snake along the Sintra Hills.

From here, I head back down to Lisbon and get on the A2 motorway for the 80-minute drive to Melides in the Alentejo region. Beyond the buzz of Comporta—a popular swoop of coast surrounded by pine forests and rice fields—Melides is all cork farms, rolling vineyards, and a seemingly endless coastline that delivers plenty of drama. Up until recently, it was a place where time (and locals) moved slowly. But high-profile developments have seen the area’s pulse quicken.

Perhaps the most heart-starting is Christian Louboutin’s hospitality debut. The French fashion designer first purchased land in Alentejo more than a decade ago, and was recently convinced—by the mayor of Melides—to open a hotel. Louboutin collaborated with architect Madalena Caiado to bring Vermelho (doubles from US$350) to life, in a style that unites maximalism and eclecticism. Many of the shoe maestro’s personal pieces adorn the 13-room property, from Spanish bargueño chests to an embroidered velvet sofa designed by Henri Samuel. Red, naturally, is everywhere, but there is also inky-blue azulejo tilework. The walls of one suite feature a fresco by Louboutin’s longtime friend, Greek artist Konstantin Kakanias, while the exterior dazzles with enormous baroque ceramic appliqués by Italian sculptor Giuseppe Ducrot.

Enjoying a more rural setting is another Melides newcomer, Pa.te.os (doubles from US$600)—the name is a play on the word “patio.” With just four minimalist concrete villas designed by Lisbon architect Manuel Aires Mateus, the 80-hectare property exudes authenticity. Look anywhere, and you’ll find only natural, solid materials in earthen hues, woven together with detail-oriented luxury.

Inside a villa at Pa.te.os, a design-driven hotel overlooking an untamed slice of the Alentejo countryside. (Photo: Francisco Nogueira)

*Left to right:* The mid-19th century Palácio da Pena in Sintra; breakfast on the balcony of a suite at Vermelho. (Photos: Luisportugal/iStock, Ambroise Tézenas)

Between the fabulous beds and in-room yoga, I find it hard to leave. When I do, I’m treated to a staggeringly beautiful coastal landscape highlighted by the striated sand cliffs of Arriba Fóssil da Galé. Also nearby is Melides Art, a creative community conceived by Portuguese entrepreneur and art collector Miguel Macedo Basto de Carvalho as a place where visiting painters, sculptors, writers, musicians, and designers can interact and find inspiration. They’re housed in residences that are striking works in their own right, set amid a sandy pine forest dotted with pieces from Carvalho’s own collection: a series of anthropomorphic marble sculptures by Swiss artist Olaf Breuning; a life-size circus bear by American Marnie Weber; and Robert Melee’s Colorful Monsters, which resemble gigantic melting candles.

My route south from Melides hugs the Vicentine Coast, the longest stretch of protected coastline in the country. A string of beaches are framed by soaring cliffs, and the untamed sea provides a natural soundtrack as I drive toward Praia do Canal Nature Resort (doubles from US$350). The design here is contemporary kasbah meets luxe Roman bath, with buildings that seem to spring from the dry earth like so many hills that decorate southwestern Portugal. Driftwood of a scale reflecting the hotel’s expansive theme adorns hallways and courtyards, and hand-hewn tables and stools help ground its restaurants to the land. The main dining room, Azeitona, takes me on a culinary journey around Alentejo, through dishes like razor clams with coriander and lemon; plump violet shrimp in fish broth; and the region’s famous black pig on harissa.

Farther south still is Sagres Point, the southwestern-most extremity of continental Europe. Its stark fort aside, the main reason to visit this windswept promontory is to surf, with some of the most challenging breaks in Portugal waiting offshore. From here, the Algarve Coast stretches 150 kilometers east to the Spanish border, skirting some of Europe’s most coveted resort towns (Lagos, Vilamoura, and Albufeira among them). In between is a parade of head-turning beaches like Falésia, whose lofty white-and-ocher bluffs have been gouged by weather into intriguing shapes.

The drive to the last hotel of my trip is wrapped in a feel-good light—long expanses of burned-butter sands; the smell of sizzling fish drizzled with olive oil; the clack-clack of storks perched in the squat trees that border the winding roads. Arriving at the freshly minted Casas Quinta de Cima (doubles from US$280) is another one of those unexpected rabbit hole moments, its nine converted farm cottages enveloped by olive, avocado, and orange groves. My host recommends I saddle up one of the estate’s horses and ride to the seaside village of Cacela Velha. “If you go now, you’ll be in time for their haul of fresh oysters,” she says.

Armed with a bottle of ruby-tinged castelão, I set off for a seafood feast. Gail Curley was right—life is never boring in Portugal.

The 19th-century facade of The Ivens in Lisbon’s Chiado district. (Photo: Francisco Nogueira)

This article originally appeared in the August/September 2023 print issue of DestinAsian magazine (“Sketches of Southern Portugal”).

Laid-back Luxury on a Journey to Southern Portugal

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