Alentejo Uncorked: A Lavish 5-Day Wine & Gastronomy Escape

Day 1

Arrival in Évora, Welcome Lunch at Café Alentejo, Private Guided Walking Tour of Évora, Candlelit Dinner at Divinus

Where You’ll Stay

Convento do Espinheiro Historic Hotel & Spa

 Convento do Espinheiro Historic Hotel & Spa is nestled just a few minutes from Évora’s 2,000-year-old Roman temple. This hotel offers an exquisite blend of regal history and thoughtful proximity to Alentejo’s wine routes, which makes it the perfect base for your 5‑day culinary and wine journey.

Dating back to the 15th century, this former monastery once hosted Portuguese royalty and clergy from the Order of St. Jerome. Lovingly restored, its gilded chapel, vaulted cloisters, and frescoed corridors now evoke centuries of devotion and architectural legacy Within its 23‑acre estate, the hotel blends two wings; a heritage section with period opulence and a sleek contemporary wing with mid-century designer touches. All rooms feature balconies or terraces overlooking lavender gardens, olive groves, or Évora’s skyline.

We chose this 5-star hotel for luxury travelers who value authentic experiences layered with elegance; for those who savor not just fine wine and cuisine, but also the stories embedded in stone walls and centuries-old traditions. With world-class dining, a wine cellar housed in a former cistern, and a spa inspired by local botanicals, Convento do Espinheiro invites you to live the rhythm of Alentejo, wrapped in quiet grandeur.

Overnight: Evora

Meals included: Breakfast

Midday

Your culinary journey begins with a scenic private transfer from Lisbon or Faro into the heart of Alentejo, arriving in the atmospheric town of Évora; one of Portugal’s most compelling UNESCO World Heritage Sites. Évora is a city shaped by centuries of civilizations; a living museum where Roman ruins rise beside Gothic spires, and Moorish courtyards spill into sun-washed plazas. Begin your exploration with a relaxed stroll through the historic center, guided by layers of heritage etched into every arch and alleyway. The grandeur of the Roman Temple of Diana, dating back to the 1st century AD, stands proudly near the medieval Évora Cathedral; its cloisters adorned with flamboyant Gothic tracery and maritime motifs, a hallmark of Portugal’s golden age of discovery.

For lunch, settle in at Café Alentejo, a beloved tavern nestled within a 16th-century noble house. With its rustic stone arches and traditional tiles, the space offers a warm, nostalgic atmosphere. This is where locals come for comfort food steeped in tradition. Savor the region’s signature açorda à Alentejana, a soulful garlic-and-cilantro broth thickened with country bread and crowned with a poached egg. We recommend pairing it with Alentejo-style ensopado de borrego, a slow-cooked lamb stew seasoned with native herbs, to understand why this region is celebrated as the breadbasket of Portugal.

Afternoon

Join a private guided walking tour of Évora, the most enriching way to appreciate the town’s layered history. As you meander through centuries of architectural evolution, your local guide will illuminate the stories behind Évora’s Roman forum, the intricate Manueline doorways, as well as the ancient aqueduct that still flows through town. This experience is a quiet homage to a region that honors its past while inviting you to bask in the present.

Evening

As the sun sets, return to the Convento do Espinheiro for dinner at its Divinus restaurant, a Michelin recommended restaurant housed in the former monastic wine cellar beneath vaulted ceilings. The ambiance is hushed and reverent; lit by candlelight and steeped in stone; everything curated with care. Here, modern culinary techniques meet monastic tradition. You’ll be amazed at how it transforms local ingredients into dishes like black pork tenderloin with river mint or braised wild mushrooms over creamy açorda. Sip a glass of Alentejo‑Évora DOC wine as you toast to the start of your immersive journey through Portugal’s most authentic wine region that is beloved by the Portuguese and still delightfully undiscovered by many foreign travelers.

Overnight: Evora

Meals included: Breakfast

Day 2

Private Tour & Tasting at Herdade do Esporão, Lunch at Estate Restaurant, Visit to Monsaraz, Gourmet Dinner at Degust’AR

Midday

The morning begins with your guide taking you to nearby Herdade do Esporão, one of the most iconic estates in Alentejo’s Reguengos subregion. This pioneering vineyard is known for its deep commitment to sustainability and biodiversity, producing award-winning organic wines that reflect the soul of the land. You'll enjoy a private tour through the estate's vineyards and medieval Esporão Tower before settling into a tasting of their flagship blends. Think barrel-aged reds and crisp Antão Vaz whites that are expertly curated for complexity and balance.

Following your tasting, lunch is served just steps away at Restaurante da Herdade do Esporão, a contemporary dining space that champions hyperlocal, seasonal cuisine. The kitchen, led by a rotating roster of top Portuguese chefs, crafts elegant dishes rooted in Alentejo's culinary traditions. Expect innovative pairings like roasted octopus with fermented pepper, lamb with smoked yogurt, or pumpkin with sheep's cheese and fresh herbs that are all accompanied by estate-grown wines and olive oils.

Afternoon

In the afternoon, make your way to Monsaraz, a hilltop village frozen in time. Encircled by fortified stone walls, this whitewashed town offers panoramic views over the Alqueva Lake and Spanish borderlands. Wander through its cobbled lanes, artisan workshops, castle ruins, or simply pause with a glass of wine at one of the quiet terraces overlooking the plains below.

Evening

As the day draws to a close, return to Évora for dinner at Restaurant Degust’AR, set within the noble walls of the M’AR De AR Aqueduto hotel. This place is recommended by the Michelin Guide for its elegant dishes and atmospheric setting. Here, chef António Nobre reinvents traditional Alentejo cuisine with sophistication and creativity. Think confit duck with quince, saffron-scented açorda, or carob-infused desserts, each beautifully presented in an ambiance that fuses historic grandeur with contemporary flair.

Overnight: Evora

Meals included: Breakfast

Day 3

Scenic Drive through Estremoz, Lunch at Mercearia Gadanha,
Wine Tasting at Torre de Palma Wine Hotel,
Elegant Dinner at Enoteca Cartuxa

Midday

Your day will start with a scenic drive through Estremoz. Known as one of Alentejo’s famed "Marble Towns," Estremoz shimmers with white stone facade and castle ramparts that tells the stories of queens and crusaders. You can walk through the town's cobbled streets toward the top of the old town, where you will see a 13th-century tower that offers sweeping views over vineyards and olive groves. Browse local pottery and antique stalls and soak in the timeless charm of this lesser-known gem in the Alentejo.

For lunch, head to Mercearia Gadanha, a modern bistro set in what used to be an old grocery store. It’s a local favorite known for creative takes on classic Alentejo dishes, made with seasonal ingredients. You might try their creamy tomato açorda topped with a poached egg or their smooth goat cheese mousse drizzled with honey and herbs. The restaurant also features a thoughtful wine list that perfectly captures small producers from nearby subregions. It’s a relaxed, welcoming space that reflects the region’s growing reputation for fresh, high-quality cuisine.

Afternoon

In the afternoon, your wine journey continues north to Torre de Palma Wine Hotel, a boutique estate near Monforte that blends Roman-inspired architecture with contemporary luxury. This family-run property is as much about heritage as it is about innovation. After a guided tour of the cellars and vineyards, relax in their airy tasting room to sample limited-edition Alentejo wines, including single-varietal reds and fresh, elegant whites.

Evening

As the sun dips low, return to Évora for dinner at Enoteca Cartuxa; an elegant wine bar and restaurant by Fundação Eugénio de Almeida. The space balances minimal design with warm hospitality that serves dishes that elevate humble Alentejo ingredients into fine cuisine. Here, you can toast to your journey with the famed Pêra-Manca red or a crisp white from Cartuxa’s private cellar.

Overnight: Evora

Meals included: Breakfast

Day 4

Winery Tour & Tasting at Herdade do Sobroso, Seasonal Lunch at Quinta do Paral, Cork Forest Walk, Dinner at O Moinho do Cu Torto

Midday

Morning will set off with a drive south toward Vidigueira, a lesser-known but historic wine subregion in Alentejo. As you travel, the scenery gradually changes from vineyards that will give way to old olive groves and cork oak forests, their branches casting soft shadows over the warm, earthy landscape. Your first stop is Herdade do Sobroso, a boutique wine estate and hotel set near the Guadiana River, close to the town of Vidigueira. The property is known for its warm terracotta buildings and sweeping views that reach all the way to the Spanish border.

Begin with a guided winery tour, where your host walks you through century-old fermentation techniques alongside modern aging rooms lined with French oak barrels. The wines here are as expressive as the terroir; sun-soaked reds with velvety tannins and citrus-laced whites that speak of schist-rich soils with limited-edition blends that echo the surrounding wilderness. After the tasting, sit down for an early lunch of traditional Alentejo dishes reimagined through a seasonal lens. Here, you will enjoy lamb slow-roasted with local herbs, creamy açorda infused with garlic and coriander, wild boar stew kissed with river mint, all paired with estate wines under a shaded veranda.

​​Your culinary journey continues just minutes away at Quinta do Paral, a beautifully restored estate that has become a rising star in Portugal’s boutique wine scene. Here, you’ll enjoy either a second light lunch or a longer tasting menu, depending on your pace. Expect regional cured meats and seasonal, vegetable-based dishes that change with the harvest. The kitchen emphasizes organic ingredients and simple, honest preparation that reflects the winemaker’s own philosophy of balance and respect for Alentejo’s farming heritage.

Afternoon

In the afternoon, trade the cellar for the living landscapes that shape these flavors. Join a local guide for a cork-oak forest walk, where you’ll trace the lifecycle of Portugal’s prized cork trees; some centuries old, and learn how this sustainable industry continues to shape Alentejo’s economy and ecology.

Evening

Head back to Évora for a laid-back dinner at O Moinho do Cu Torto as the night falls. This spot just outside the city’s historic walls is well-loved by locals and tourists alike. O Moinho do Cu Torto is housed in a former mill which gives it this cozy, countryside feel. Adorned with terracotta floors and a wood-fired oven at its center, you will feel Alentejo at its core. There’s no set menu, only what the family has cooked that day. You might be served a hearty chickpea and pork stew or tender stewed partridge flavored with coriander and river mint.

Overnight: Evora

Meals included: Breakfast

Day 5

Leisurely Morning in Évora Markets or Artisan Shops, Final Lunch at Dom Joaquim, Departure to Lisbon or Faro

Midday

Your final morning in Evora will be spent soaking in the slower, more-normal rhythm of local life. A visit to the markets where vendors sell pao Alentejano and golden olives from the groves nearby, and small artisan shops that offers handwoven blankets, traditional ceramics and all sorts of locally-produced goods will transport you to a simpler, quieter pace of living. If you're not up for shopping, you can opt for a quiet walk through the cobbled streets to soak in the last views of Roman ruins and medieval arches lit by the early sun.

For lunch, indulge in a final Alentejano feast at Dom Joaquim, one of Évora’s most celebrated kitchens and a fitting stage for your gastronomic farewell. Here, rustic tradition and culinary finesse is blended perfectly, so expect dishes like braised black pork with pennyroyal, slow-cooked stews fragrant with garlic and bay, and seasonal sides showcasing garden-fresh produce. The wine list is equally regional, drawing from DOC labels you’ve now come to know by taste and terroir.

Afternoon

As the afternoon approaches, check out of your hotel before getting transferred back to Lisbon or Faro for your onward journey. With your bags full of local delicacies and your senses steeped in the sunlit pleasures of Alentejo’s wine lands, you’ll leave with memories and deeper connection to this soulful, slow-burning corner of Portugal.

Meals included: Breakfast