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

Day 1

Arrival in Évora & Private Guided Walking Tour

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

Morning

Your culinary journey begins with a 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. Shaped by centuries of history, Évora is a living museum where Roman ruins stand beside Gothic churches and Moorish courtyards open onto sunlit squares.

For lunch, you may wish to dine at Típica Quarta-Feira, one of Évora’s best-known restaurants for traditional Alentejo cuisine. Known for its warm, rustic atmosphere, it offers a generous selection of regional dishes and local wines in a relaxed setting. Lunch is optional and not included in the price.

Afternoon

After lunch, join a private guided walking tour of Évora, one of the best ways to discover the city’s rich history. As you explore its historic streets, your local guide will reveal the stories behind landmarks such as the Roman Temple of Diana, the medieval Évora Cathedral, elegant Manueline details, and the old aqueduct that still runs through the town. It is a rewarding introduction to a region that preserves its heritage with quiet confidence.

Evening

As the sun sets, you may choose to have dinner at A Cozinha do Paço, the Michelin-starred restaurant at Fitapreta, around 10 to 15 minutes from Convento do Espinheiro by car. Dinner is optional and not included in the price. Set within the restored Paço do Morgado de Oliveira, a 14th-century estate surrounded by vineyards and countryside, the setting feels both historic and serene. The restaurant offers contemporary Portuguese cuisine inspired by Alentejo’s traditions, local produce, and the estate’s wines. Paired with Fitapreta wines, it makes an elegant introduction to the flavours and character of the region.

Overnight: Evora

Day 2

Private Tour and Tasting at Herdade do Esporão with Lunch,
Visit to Monsaraz

Morning

The morning begins with your guide taking you to nearby Herdade do Esporão, an iconic estate in Alentejo’s Reguengos subregion known for its sustainable, award-winning organic wines. You’ll enjoy a private tour of the vineyards and medieval Esporão Tower, followed by a tasting of barrel-aged reds and crisp Antão Vaz whites.

Following your tasting, lunch is served at Restaurante da Herdade do Esporão, a contemporary dining space focused on hyperlocal, seasonal cuisine. Expect elegant dishes rooted in Alentejo’s culinary traditions, served with 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 Alqueva Lake and the Spanish borderlands. Wander through its cobbled lanes, artisan workshops, and castle ruins, or pause with a glass of wine at a quiet terrace overlooking the plains below.

Evening

As the day draws to a close, return to Évora. Dinner is at leisure, with a recommendation to dine at Restaurant Degust’AR in the M’AR De AR Aqueduto hotel. Recommended by the Michelin Guide, it offers chef António Nobre’s refined take on traditional Alentejo cuisine in an elegant historic setting.

Overnight: Evora

Meals included: Breakfast

Day 3

Scenic Drive & Leisurely Time in Estremoz,
Wine Tasting at Torre de Palma Wine Hotel

Morning

Today is a leisurely day in Estremoz, one of Alentejo’s famed Marble Towns. White stone façades and castle ramparts tell stories of queens and crusaders. Stroll the cobbled streets to the top of the old town, where a 13th-century tower overlooks vineyards and olive groves. Browse pottery and antique stalls, and enjoy the timeless charm of this lesser-known Alentejo gem.

For lunch, we recommend Mercearia Gadanha, a modern bistro in a former grocery store. Lunch is optional and not included in the price. A local favourite, it serves creative Alentejo dishes made with seasonal ingredients, alongside a thoughtful wine list featuring nearby producers.

Afternoon

In the afternoon, continue north to Torre de Palma Wine Hotel, a boutique estate near Monforte that blends Roman-inspired architecture with contemporary luxury. After a guided tour of the cellars and vineyards, relax in the tasting room and sample limited-edition Alentejo wines, including single-varietal reds and elegant whites.

Evening

As the sun dips low, return to Évora, where we recommend dinner at Tua Madre, not included in the price. In the historic centre on Alcarcova de Baixo, this stylish restaurant offers a contemporary menu shaped by Italian, Mediterranean, and Portuguese influences, making it a relaxed way to end the day.

Overnight: Evora

Meals included: Breakfast

Day 4

Winery Tour & Tasting at Herdade do Sobroso,
Seasonal Lunch at Quinta do Paral,
Cork Forest Walk

Morning

In the morning, head south towards Vidigueira, a historic wine subregion of Alentejo. As you travel, vineyards give way to olive groves and cork oak forests across the warm, earthy landscape. Your first stop is Herdade do Sobroso, a boutique wine estate and hotel near the Guadiana River, close to Vidigueira, known for its terracotta buildings and far-reaching views.

Begin with a guided winery tour, where your host introduces traditional fermentation techniques alongside modern ageing rooms lined with French oak barrels. The wines reflect the terroir, from velvety reds to citrus-laced whites shaped by schist-rich soils.

Your culinary journey continues a few minutes away at Quinta do Paral, a beautifully restored estate in Portugal’s boutique wine scene. Here, you will enjoy lunch, with regional cured meats and seasonal dishes prepared with organic ingredients and a simple, balanced approach.

Afternoon

In the afternoon, trade the cellar for the landscapes behind these flavours. Join a local guide for a walk through the cork oak forest and learn how Portugal’s prized cork trees continue to shape Alentejo’s economy and ecology.

Evening

For dinner, we recommend returning to Évora for a relaxed evening at O Moinho do Cu Torto. Just outside the historic walls, this former mill has a cosy countryside feel, with terracotta floors and a wood-fired oven at its centre. There is no set menu, only what the family has cooked that day. Dinner is at your own expense and is not included in the price of the itinerary.

Overnight: Evora

Meals included: Breakfast

Day 5

Leisurely Morning & Departure

Your final morning in Évora is yours to enjoy at leisure at Convento do Espinheiro. After breakfast, take a gentle stroll through the hotel grounds, soak up the sun from a lounger by the pool, unwind in the hotel spa, or enjoy a quiet swim in the indoor pool. Check out of your hotel before your transfer 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 a deeper connection to this soulful, slow-burning corner of Portugal.

Meals included: Breakfast