Things to do in the Alentejo region in Portugal Stories > Experiences > Things to do in the Alentejo region in Portugal Kerry MurrayThe Alentejo region of Portugal has been in the news quite a bit recently: the New York Times listed it as one of “52 Places to Go in 2015” and several other publications have followed suit, dubbing it the “new Tuscany” and extolling the virtues of this wine and olive oil-producing region. This positive publicity has done great things for tourism in the area, and the star attractions and larger cities such as Évora are welcoming an ever-increasing flow of visitors. The beauty of this part of Portugal, however, lies in the smaller towns and off-the-beaten-track sights, which are waiting to be visited. For those of you with a love of vast landscapes, amazing vistas and a passion for historical attractions and medieval architecture, there is a series of small, fortified villages along the Spanish-Portuguese border that are well worth exploring. Like most other border towns with ancient origins, the purpose of their existence was to protect against invading enemy troops. Architectural styles vary from North to South, but common characteristics they share are that they all boast an impressive castle and are perched on top of a hill or promontory with an unobstructed view for kilometres in all directions. Tailor Made JourneyTravel Like a VIPMr Hudson designs unique and exclusive vacations for sophisticated gay travelers who prioritize beauty, style and belonging. BOOK WITH US Moorish architecture in MértolaStarting in the south, the town of Mértola was founded on the banks of the Guadiana River that flows south to the Algarve coastline and was strategic for transporting goods inland. The town´s position on the river meant that it has seen its fair share of battles and occupations throughout the centuries. The Moors had control of the town for quite a long time (from the 700’s until the 1200’s), and the Islamic influence is very obvious in much of the older buildings. The main church itself was originally a mosque, converted to a church by the Knights Templar during the “Reconquista” (reconquest) in the 13th century. Mértola still celebrates her Moorish heritage and hosts an Islamic Festival every May, which is the highlight of this sleepy town´s social calendar. Monsaraz | Photo: Emanuele Siracusa The Alentejo region is famous for its bread and olive oil, and much of the local cuisine is based on these two staplesMedieval MonsarazFrom here it is a short drive to Monsaraz, which is probably the most famous of all the towns on this route. This area has been occupied since prehistoric times, and the rocky outcrop that is the site of the present-day castle is considered to be one of the oldest settlements in southern Portugal. The plains surrounding the village are also home to hundreds of megalithic monuments dating back to between 4,500 and 2000 BC. If you are into really old stuff, then this is the place for you. The Alentejo region is famous for its bread and olive oil, and much of the local cuisine is based on these two staples. The “Templarios” tavern, situated within the town walls, is a medieval-style tavern and restaurant serving typical Alentejo cuisine. The menu features a wide range of local produce such as goats cheese, Iberian ham, wild boar cooked in a variety of ways and many other regional dishes that haven´t changed much over the centuries. The views from the town are spectacular in all directions, and you can clearly see Spain across the sky-blue waters of the Alqueva Lake. In several places, you can walk up onto the fortified walls surrounding the town for a 360-degree panorama. Photo: Emanuele Siracusa Going to Portugal? The same team that brings you the content you love designs your perfect tripWine and luxury in MonforteOn the road again, keep heading north via the city of Elvas towards Monforte, a sleepy town in the Alto Alentejo. This is where you will find the Torre de Palma Wine Hotel, a highly acclaimed hotel and restaurant as well as award winning wine estate. Dating back to 1338, the estate buildings have been fully restored and blend the past with the present without losing the historical atmosphere or compromising the unique Alentejo light, reflected in abundance through the white rooms and minimal styling of the restaurant and spa. Here, you can do as much or as little as your heart desires. If you are tending more towards the lazier end of the spectrum, there is an amazing indoor pool and spa where you are free to do nothing at all for as long as you like. Or for those in search of a bit of activity, the hotel hosts wine tastings in the cellar, cooking workshops and can organise all manner of outdoor activities for guests; horse riding, walking tours of local Roman ruins and even a hot air balloon ride, an incredible way to view the surrounding landscape.Monforte also serves as the perfect base from which to venture out and explore other towns in the region. From here you could double back south again to visit the historic city of Elvas, a Unesco world heritage site since 2012 and famous for its military architecture and extensive fortifications. Alternatively, head north via the district capital of Portalegre to Marvão, a small, whitewashed village perched on top of a high granite outcrop in the São Mamede Mountains. As you can imagine, the views are incredible, and it is because of this strategic position that the outcrop has been populated since pre-Roman times. Mertola | Photo: Emanuele Siracusa Portalegre | Photo: Emanuele SiracusaStepping back in timeNearby, a bit lower down in the mountain slopes, lies the town of Castelo de Vide. Together with Marvão and the Spanish town of Valencia de Alcântara, this triangle boasts one of the most concentrated areas of megalithic sites in all of Europe and there are more than 200 monuments within a 25km radius, from the Neolithic, Bronze and Iron Ages. Rated as one of the best-preserved medieval towns in Portugal, Castelo de Vide also boasts the oldest synagogue in the country, dating back to the middle of the 15th century and located in the Jewish quarter. This pretty little town with her winding cobblestone roads and panoramic vistas marks the northern-most point on this tour of Alentejo border towns. Of course, the border continues north and so do the historical fortresses; there are many more to be explored, but on another day, perhaps.Want to simplify luxury travel planning?Whether you want a resort vacation, wildlife safari, city break, luxury cruise, wellness retreat, honeymoon, once-in-a-lifetime adventure or weekend escape, the trip curation experts at Mr Hudson make travel planning a breeze. Contact us to find out how we can handle the finer details of vacationing in style.Special SelectionExclusive Mr Hudson offersOut now from gestaltenMr Hudson Explores Browse the Book share Torre de Palma | Photo: Kerry Murray Photo: Emanuele Siracusa Torre de Palma | Photo: Kerry Murray Torre de Palma | Photo: Kerry MurrayDid you enjoy this article? Then sign up for our newsletterDid you enjoy this article? 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