4 Days in Alentejo, Portugal

Centrally located, Évora is a great home base for your time in this beautiful region. Rent a car near Lisbon airport and head straight out of the city. (Trust me, you do NOT want to drive in Lisbon!) En route to Évora, stop at Cromeleque dos Almendres, a circular arrangement of standing stones dating back to the Neolithic period, around 6000-4000 BCE. It is one of the largest and most significant megalithic sites on the Iberian Peninsula and is believed to have had ritual and astronomical significance.

After checking into your hotel, spend the afternoon sightseeing in central Évora. Start at the Chapel of Bones, a macabre chapel lined floor-to-ceiling with human bones (two monks’ solution to a lack of cemetery space). Next, walk over to Templo Romano, one of the largest Roman ruins in the area and once thought to be a temple to the Goddess Diana. Grab a drink and a snack at the nearby Jardim Diana kiosk and enjoy the view and people-watching.

After a stroll through Évora’s quaint streets or some down time at your hotel, enjoy dinner at Restaurante A Bruxa D'Évora. This intimate and inviting restaurant serves up classic Portuguese cuisine with a modern touch and careful attention to detail. Be sure to explore the booth seating area and bathrooms to observe the creative transformation of this former stable, showcasing how it has retained elements of its historical use.

Tip: While there are plenty of great dining options in Évora, many offer only a handful of tables and one seating per night. Be sure to book dinner reservations in advance of your stay.

Today your activities will focus on Alentejo’s agricultural history and amazing wine! Arrive at the Rota dos Vinhos do Alentejo Tasting Room at 10:00 a.m. Learn about the history of winemaking and the winemaking process at the center’s informative exhibit. If you don’t mind a glass of wine before lunch, this tasting room offers a rotating selection from multiple wineries that will give you a great introduction to the region’s wine.

Next, take a drive through the Alentejo countryside to Redondo for a tour with Corktrekking. Corktrekking offers walking and 4x4 tours on Herdade da Maroteira, a working ranch complete with a cork forest, cattle and vineyards. In your private tour, you will learn about the process of harvesting cork, the wine varietals growing on the property and much more. After the tour, enjoy a private wine tasting of the estate’s vintages at their wine-making facility. Corktrekking also offers the option to add lunch at a traditional Portuguese restaurant to your tour package.

On your way back to Évora, stop at one or two adegas (wineries) to take in more beautiful vineyard views while sipping wine. The Rota dos Vinhos do Alentejo website provides information on area wineries, including tasting room hours. Tip: I recommend making advance reservations to ensure they are prepared for your visit.

This evening, enjoy a fantastic traditional Portuguese dinner at Taberna Típica Quarta-feira. Chef João creates an atmosphere akin to dining in a large family dining room and takes time to personally greet each guest. The menu is set in advance, so come with an open mind and a big appetite! I promise this will be one of those meals you talk about for a long time.

On Day 3, drive to the hilltop village of Monsaraz for the day. The village consists entirely of pedestrian streets, so you’ll park just outside of the castle wall and walk in. Enjoy wandering through the village’s streets and alleys, admiring the old bullfighting ring and white-washed buildings, walking on the castle wall and taking in amazing views of the Portuguese countryside. Looking east on a clear day, you can see across Lago Alqueva all the way to Spain.

Stop for lunch at Xarez (Rua de Santiago 33) and enjoy spectacular views on their terraced patio while savoring Alentejo wine, bread and cheese. Monsaraz has a number of boutiques selling high-quality handmade home goods and other items. I highly recommend a stop at Fabrica Alentejana Lanificíos (on Rua do Celeiro), which sells beautiful hand-woven wool textiles in traditional Portuguese patterns. (Tip: Textile lovers may want to visit Fabrica Alentejana Lanificíos’ factory to get an up-close view of master weavers in action. Advance reservations are required.) Before heading back to Évora, make a quick stop at Cromleque do Xerez, another Neolithic monument just north of Monsaraz.

Enjoy dinner at Enoteca Cartuxa, another delicious restaurant in central Évora. Cartuxa is a local adega and you’ll find many of their wines, along with other Alentejo options, on their extensive wine list.

Check out of your hotel and begin the drive back to Lisbon. If you aren’t quite ready to get back to the bustle of the city, make a stop at the castle at Montemor-o-Novo on the way. You may have seen quite a few castles during your time in Portugal, but this one is off the beaten path and you’ll get enjoy the lack of crowds. This castle is also an active archaeological dig with an opportunity to view the pits where work is currently taking place.

After Montemor-o-Novo, head back over the Vasco da Gama bridge into Lisbon and return that rental car before you get stuck in a narrow, one-way, cobblestone alley! Ubers in Lisbon are cheap and can take you the rest of the way into town if you aren’t taking a rental company shuttle to the airport.