Vino, Views, and Vintage Moments: Discovering the Soul of Southern Portugal

Whether you're planning a relaxing retreat with friends or a dreamy group getaway, Southern Portugal offers the perfect mix of indulgence and adventure. From savoring sun-soaked afternoons in picturesque vineyards to sharing unforgettable meals at hidden culinary gems, this guide will help you discover the best spots to sip, savor, and soak up the region's charm. Gather your crew and get ready for an unforgettable journey through one of Europe’s most enchanting destinations.

Hotel Das Amoreiras 

​​Thanks to a red-eye flight from New York, I land in Lisbon around noon, ready to hit the cobblestone streets. My first stop is Hotel Das Amoreiras, a jewel-box of a hotel nestled in one of the city's prettiest neighborhoods. Overlooking a charming, tree-lined park, this boutique property features 17 rooms and two suites and offers travelers a blend of sophistication and whimsy. In the white-washed courtyard, where the afternoon light bathes a single olive tree, my mother and I are greeted with homemade iced tea, served with pink swizzle straws. Inside, a film poster for James Bond’s Octopussy hangs above the technicolor bar—touches playfully envisioned by owner Pedro Oliveira, who founded the hotel along with his wife, Alicia Valero. It all feels very home away from home, if your home had a stunning art collection, peaceful courtyard, prime location, and great sense of humor.

 

Before we leave the hotel, the attentive staff sits down with us to map out an entire walking tour of the city. Our first stop is the Principe Real neighborhood, where, on the hotel's recommendation, we head to Pica-Pau for their leggiero-style octopus—drizzled with olive oil, loaded with garlic, and served alongside thick roasted potatoes,  a signature creation by Chef Luís Gaspar. The cheerful yellow of Lisbon's famous trams echoes through the vibrant cityscape as we continue our stroll. We make our way to the Miradouro de São Pedro de Alcântara viewpoint, snapping selfies with terracotta rooftops and the Tagus River as our backdrop. Clean lines and pops of color are everywhere. Lisbon is a city made for meandering, so it’s easy to wander through its steep, sloping streets until evening descends, casting a dreamlike glow.

 

 

My mom and I spend the next two days eating our way through the city. There’s dinner at Magnolia, a quaint wine bar about a 10-minute walk from Hotel Das Amoreiras. Opened in 2022 by owners from Brazil and Belgium, we share and savor dishes like mango carpaccio, lamb meatballs, and shiitake polenta, with a wide selection of local and natural wines available to pair. The bar's ceiling resembles a tiny chapel, complete with intricate molding and a fresco of a topless angel. After dinner, we step out into the crisp September evening and head to Nannarella for thick scoops of gelato. On our way back to the hotel, despite it being 10pm on a Tuesday, we pass the park, which is buzzing with life, thanks to the quiosques de refrescos—small, ornate kiosks serving traditional Portuguese snacks, drinks, and coffee. With our park-facing room, I drift to sleep listening to laughter and church bells.

The next afternoon there’s lunch at Leonetta. Under shelves filled with glass bottles, jugs of dried flowers, and a gallery wall with (highly Instagrammable) framed pictures taken from the owner’s personal family archives, I twist a decadent swirl of creamy seafood pasta, featuring hunks of lobster, fennel, and mascarpone sauce. By the time the dish is done, I unbutton my pants as I lean back into my powder-blue dining chair. But there’s more walking and eating to be done. We visit the upscale streets of Chiado, the grand plaza of Praça do Comércio, and Avenida da Liberdade, and with the help of Hotel Das Amoreiras, manage to snag a 9:30pm reservation at Prado, which I later learn means "Meadow" in Portuguese.

 

 

Housed in a former fish factory, Prado is sleek and modern, featuring hanging plants and an industrial Brooklyn vibe. We opt for the nine-course tasting menu, which includes biodynamic wines, grilled energy mushroom with goat cheese and lard, yellow belly grouper with pil pil and kale, and acorn-fed Alentejano pork with potato, ham, and spinach. The velvety pork serves as a preview of what's to come, as we head to the Alentejo region the next day, two hours outside of Lisbon.

L’AND Vineyards

The next morning, at Hotel Das Amoreiras, what now feels like our extended family helps us pack the car before we set south towards the expansive, honeyed landscapes of Alentejo.

We arrive at L’AND Vineyards at dusk. The stark modernism of the hotel lobby, with its clean lines and minimalist furniture, feels like a palette cleanser against the gnarled, vineyard landscape. The lobby is sparse, with eucalyptus wood accents adding warmth, and from the dining room, beneath a bouquet of golden Tom Dixon lights, we have an uninterrupted view of an infinity pool and small lake. Far off in the distance, a crumbling white castle perches on a hilltop, adding historic charm.

 

 

As we’re guided to our room, I can’t help but notice the bumpy, yellow, apple-shaped fruit hanging from the trees encircling the pool. “Those are quince trees,” our host explains with a smile. “We use them to make the marmalade served at breakfast.” My mouth waters.

 

 

Soon, we arrive at one of L’AND’s famed “sky view suites,” a name that feels perfectly fitting. The suite’s retractable roof offers the rare luxury of sleeping under a blanket of stars framed by a glass window. Outside, a small fire pit overlooks the lake, exuding the same warmth as the spiced cake with lavender and dried fruit waiting for us inside. Beneath the cake, a playful note reads, “Enjoy with your hands.”

We change, walking back over to the dining room for dinner at MAPA, where the menu is curated by Chef David Jesus, a celebrated figure in Portuguese gastronomy with experience in some of the country’s most prestigious kitchens, including time spent working under José Avillez. The meal feels like an exploration of history, with a menu reflecting Portugal’s evolving tastes, influenced by trade, colonization, and commerce. Each dish tells a story: matapa, a spicy Mozambican stew of greens, shrimp, and peanuts, nods to Portugal’s ties with Africa, while Azorean tuna with miso, tempura, and pickled seaweed celebrates the enduring connection with Japan. Every course is paired with trivia that adds historical context, making the meal both enlightening and unforgettable. It’s a delicious reminder of how connected and wonderful the world is, whether you're eating cake with your hands or indulging in a Michelin-starred masterpiece.

 

 

After dinner, we walk back to our suite, the scent of the fire pits that surround each suite lingering in the September air. The next day, I spend time reading by the lake before attending a wine tasting, where I get to craft my own wine to be shipped home—a personalized souvenir of the trip. For those with a deeper curiosity about wine, the resort offers immersive experiences, including guided vineyard tours, biodynamic winemaking lessons, and expert-led tastings. Guests seeking relaxation can indulge in the Vinotherapy Spa, where treatments incorporate grape seeds, skins, and other wine by-products for a uniquely restorative experience.

It’s an easy place to drink in, but we head southeast for one final stop.

Herdade da Malhadinha Nova

Are we in the right place? That’s the first thought that crosses my mind as our car bumps along a long, dusty road, passing a sprawling whitewashed home tucked behind arched wrought-iron gates. Later, we’ll learn that this is the family home of the Soares family, the visionary owners of Herdade da Malhadinha Nova.

 

 

This 450-hectare estate, purchased in 1998, was born from a dream to transform an abandoned farmland into a thriving vineyard and luxury retreat. Over the years, the Soares family has lovingly restored the land, blending biodynamic winemaking practices with modern hospitality to create an experience that honors the Alentejo’s rich heritage.

As we park the car, the sounds of the estate surround us: roosters crowing, chickens clucking in the coop, and a sleek black cat darting across the path. The sheer size of the property is humbling, a sprawling expanse that is home to Portuguese Lusitano horses, Alentejana cows, Iberian black pigs, and Merino sheep. Beyond the vineyards, cork trees dot the rolling hills, their knotted trunks lending texture to the landscape, while the grapevines, planted in neat rows, stretch endlessly under the setting sun. A baby lamb is born during our three-day stay, a gentle reminder of the cycle of life that thrives on this remarkable estate.

The property has a unique layout, thoughtfully divided into houses and suites, each offering its own secluded corner of comfort across the estate. Guests can move between them via old-school Land Rovers or private golf carts, adding a sense of safari-esque adventure to the experience. One morning, my mother and I even find ourselves face to face with a reddish-brown bull, its gracefully curved horns arching upward and outward. It had escaped the pasture and wandered over to our suite, perfectly encapsulating the untamed charm of a stay at Herdade da Malhadinha Nova.

During our stay, we settle into Casa das Pedras, a terra-cotta-hued suite that feels like an extension of the golden plains surrounding it. The design is both earthy and inviting, with a private plunge pool and floor-to-ceiling glass windows that frame the landscape perfectly. Thoughtful details are everywhere, from the Vista Alegre teacups adorned with monarch butterflies to my name delicately embroidered on the pillow. The interiors, curated by Rita Soares, seamlessly blend antiques, local craftsmanship, and treasures sourced from around the world, creating a warm and welcoming retreat.

 

 

The highlights of our stay are countless. One afternoon, I took a pottery class with Rita, taught in a newly built studio gifted to her by her husband for their anniversary—a space filled with creativity and love. Mornings began with fresh orange juice and homemade bread at the country house, and evenings concluded with a barbecue under a star-strewn sky. The Soares family personally greets every guest, their warmth palpable throughout the estate.

Dining at the on-site restaurant, Malhadinha, is also—no surprise—a celebration of the land, guided by Executive Chef Joachim Koerper. Born in Saarbrücken, Germany, Chef Koerper's career spans five decades. His journey includes working in L'Ambroisie in Paris and Moulin de Mougins on the French Riviera, both three-Michelin-starred restaurants. In 2004, he co-founded Lisbon's acclaimed Restaurant Eleven, earning a Michelin star within its first year.

My risotto comes served in a pumpkin, and the zucchini, carrots, and rosemary are pulled fresh from the estate’s herb garden. The cakes are infused with lemons harvested from the property. As we drive back to our suite after dinner, the sky explodes with stars. The silence of the night feels like a rare treasure.

The estate’s vineyard is equally personal. The Soares children design the brand’s wine labels—think a zebra drawn with thick crayons. The wines are crafted with a commitment to sustainability, using natural fertilization from sheep grazing in the vineyards and rose bushes to detect diseases. Malhadinha Nova was one of the first estates to earn the Sustainable Production seal from the Alentejo Wines Sustainability Program. Solar energy powers the accommodations, and treated water is reused for irrigation. An innovative, eco-conscious ethos runs through every detail of the estate’s operation.

 

 

One personal highlight was a picnic the property arranged in the vineyard. Beneath the sprawling canopy of a centuries-old holm oak, my mother and I savored a feast of chickpea and cod salad, melon and shrimp, and local delicacies, all paired with the estate’s wines. A small speaker perched on a stack of hay played Sam Cooke’s rendition of What a Wonderful World, blending effortlessly with the rustling vineyard leaves. It was the perfect celebration of the food, the land, and the time spent together—a moment that showed how new places can hold the warmth of home in their own way.

Story by: Dylan Essertier

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