Villages and Vineyards: Insider’s Guide to the Alentejo, Portugal

The insider advice on this page is from one of Wendy’s Trusted Travel Experts for Spain and Portugal: Virginia Irurita of Made for Spain & Portugal.

Trusted Travel Expert

Virginia Irurita

Born and raised in Spain, Virginia left a decade-long career in banking in London and Madrid to found her boutique trip-planning firm in 1999. By popular demand, she later expanded her scope to include Portugal too—a natural fit, given that she speaks Portuñol (a mix of Spanish and Portuguese). She has a little black book thick with the names of local experts—museum curators, architects, chefs, flamenco dancers—eager to show you their corners of the Iberian peninsula. Her bespoke itineraries extend to the Balearic Islands, Azores, and Madeira too. Virginia has a particularly keen interest in wine and winemaking—so keen, in fact, that she bought herself a vineyard on the banks of the Douro River—and she is especially well-connected in the foodie world. So, if you’re planning a corporate retreat in the wine country or a cultural tour for museum benefactors, look no further. Virginia’s savvy local drivers and clever guides will save you considerable time and hassle. If you prefer to rent a car and drive yourself, or you’re seeking more limited arrangements, click to Ask Wendy for a different recommendation.

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Trips have a 7-night minimum and start at $1,000 per day for two travelers; she has a planning fee of 500 euros that serves as a deposit toward the trip cost. No villa rentals or self-drive trips. NOTE: Virginia is only taking trip requests that are more than 45 days before the trip start date.

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Things to Do and See

Most underrated place
Vila Viçosa is a charming town known as the “Princess of the Alentejo.” Its highlight is the Ducal Palace, once the residence of the powerful House of Braganza, with grand halls, marble façades, and centuries of history. The town is also known for its marble quarries, and you’ll see the stone everywhere—from palaces to fountains and even sidewalks. Despite its royal past and architectural beauty, Vila Viçosa remains surprisingly quiet, making it your secret discovery to explore at your own pace.

The Ducal Palace in Vila Viçosa draws from the region’s rich marble quarries. Photo: Shutterstock

Most overrated place
Comporta is beautiful but it’s gotten too touristy. During the summer, the beach gets truly packed by locals, many of whom bring boisterous, loud kids.

Hidden gem
Monsaraz is an exquisite medieval walled village with the oldest bullfighting arena on the Iberian Peninsula.

Bragging rights
Virginia can arrange for you to spend the morning visiting the Lóios Church and the Palace of the Dukes of Cadaval in Évora with Dona Diana Álvares Pereira de Melo, Princess of Orléans, 11th Duchess of Cadaval, Duchess of Anjou, who will personally show you its impressive collection of art and manuscripts. After this exclusive private tour, join the Duchess for a traditional meal and a fascinating conversation about her life and heritage.

Learn about wine from the owner of one of Alentejo’s most famous quintas, or farms. This palace-like country house, built at the beginning of the 18th century, is as famous for its Baroque architecture as for its wines. Explore the grounds and the gorgeous walled garden, a spectacular oasis filled with palm trees and stories of the aristocrats who once spent hot summer afternoons within its cool walls. Then check out the exquisite Portuguese tile and marble work inside the house, and enjoy a wine tasting and traditional lunch with the owner.

How to spend a lazy Sunday
Drive the peaceful roads of the Alentejo, enjoying the vistas of vineyards, olive trees, and flowers. Or go for a hike in the montado—a common landscape that combines woodland and pastureland, with citrus and olive plants growing beneath centuries-old cork trees, all attracting wildlife.

The Alentejo’s serene roads pass through vineyards, olive groves, and floral fields. Photo: Shutterstock

Where to Stay and Eat

Best-value splurge hotel
São Lourenço do Barrocal is a historic estate nestled among oak trees, olive groves, and vineyards. This five-star hotel offers rooms, suites, and cottages that reflect the tranquility of the Monsaraz foothills. Guests can enjoy a prodigious wine cellar, outstanding restaurants, and a strikingly designed spa without losing touch with the region’s rural heritage.

São Lourenço do Barrocal’s quiet luxury reflects the area’s tranquility. Photo: Timothy Baker

Best bang-for-your-buck hotel
The Octant Évora is a contemporary retreat in the heart of the Alentejo, designed to blend seamlessly with the surrounding landscape; rooms and villas are decorated in warm earth tones and natural wood. The property also includes two outdoor swimming pools, a serene spa, an orchard and vegetable garden, and a restaurant serving seasonal cuisine that highlights local flavors.

Restaurants the locals love
Divinus Restaurant, inside the Convento do Espinheiro hotel, serves traditional Alentejo cuisine inside the former monastery’s wine cellar; don’t miss the chestnut soup (sopa de castanha).

Restaurante Fialho is one of the most popular restaurants in Évora. Try their black pork with traditional migas, a kind of bread pudding (porco preto com migas tradicionais).

Dishes to try
In the inland Alentejo, try the baby lamb chops (costeletas de cordeiro); they are fantastic at O Moinho do Cu Torto, in Évora.

On the coast, try rice with shrimp (arroz com camarões). You’ll find a delicious version at just about every local restaurant.

Fresh produce is a colorful hallmark of Alentejo cuisine. Photo: Timothy Baker

Meal worth the splurge
Tasquinha de Oliveira, in Évora, has only a handful of tables and serves local dishes with ingredients of the highest quality. The owner himself will likely give you his personal attention.

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