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An Extremadura & Alentejo Sojourn

Embark on a less-trodden journey into the beautiful province of Extremadura in Central Spain uncovering the age-old traditions and heritage, cuisines and medieval towns with a combination into the stunning and idyllic countryside of the Alentejo region in Portugal on a road-less-travelled journey. 


Experience Medieval villages and towns of Extremadura & Alentejo

Savour exquisite wine and gastronomy

Experience the charm and allure of the countryside

Stay in charming and intimate boutique hotels



We leave Madrid this morning to begin our journey. Our first stop is the UNESCO-listed city of Avila where we discover the medieval charms, Romanesque and Gothic architecture of this impeccably well-preserved pilgrimage site and birthplace of Saint Teresa. With your specialist guide, admire the stunning walls and towers before enjoying a visit to the beautiful Avila Cathedral and the Basilica de San Vicente. Thereafter, we continue our drive to the medieval town of El Barco de Avila, dominated by the stunning backdrop of the Sierra de Gredos mountain range. Visit the 12th Century Castillo de Valdecorneja, overlooking the spectacular River Tormes and its medieval bridge. Next, a short drive arrives us into the Extremadura region where we check in at the Hospederia Valle del Jerte and time to immerse in the stunning surroundings of the Spring season. 

Overnight: Hospederia Valle del Jerte, Jerte Valley

Meals: NIL


A spectacular day of epic proportion beckons as you are treated to a cherry blossom extravaganza like nowhere else in the world (not even Japan!) In Spring, prepare yourself for a spectacle of over two million cherry trees in full blossom bathing the Jerte Valley in a blanket of white. Following cherry cultivation traditions, the cherry trees are grown in the traditional way on terraces carved out of the high mountainsides of the Jerte Valley. With your specialist nature guide, embark on a 4x4 vehicle where the day is spent uncovering spontaneous experiences, making exemplary panoramic photo stops and interactions with locals, farmers. We will spend the second half of the day discovering the wondrous nature of Garganta de los Infiernos, the "Gorge of Hell" where you will be treated to a dazzling work of nature with natural waterfalls, cascades, streams and rock pools carved by the erosion effect of the Jerte River. Enjoy the slow life immersing in nature with picnic-styled lunch. 

Overnight: Hospederia Valle del Jerte, Jerte Valley

Meals: Breakfast & Picnic Lunch


We leave the Jerte Valley today journeying south to the historic city of Plasencia, part of the ancient pilgrimage and trade route of the "Ruta de la Plata" connecting the south of Spain to the north. Discover one of the gems of the Extremadura region visiting its charming Plaza Mayor main square, the Episcopal Palace, the atmospheric Palace of the Marquises of Mirabel, Las Torres Palace and the unmistakable San Vicente Ferrer Convent. Our next stop will then be a pleasant drive to the village of Guadalupe where visit the UNESCO-listed Royal Monastery of Santa Maria de Guadalupe, an outstanding monument of epic significance built in the 14th Century dedicated to Mary. Explore the complex's scintillating architecture which comprises of the temple-basilica, the auditorium building, the Mudejar period cloister and the Gothic cloister. 

Next, a pleasant drive takes us to the romantic village of Trujillo, one of the most beautiful and well-preserved medieval towns in Spain evoking timeless moments at the many labyrinths of lovely mansions, pretty courtyards and charming gardens. Finally, a short drive arrives us into the medieval capital city, Caceres, checking in into the gastronomic Atrio Restaurante Hotel

Overnight: Atrio Restaurante Hotel, Caceres

Meals: Breakfast 


Today, we discover the magical and UNESCO-listed city of Caceres, a delightful blend of old and new. With your specialist guide, we start our discovery from the stunning Plaza Mayor, one of the most beautiful piazzas in Spain and home to the Moorish tower of Torre del Bujaco, built in the 12th Century by the Arabs to defend against the Spanish conquistadors. With informative commentary from your guide, walk through the labyrinth of charming old streets, turreted defense walls, archways and cobbled squares of the Old City while admiring the nostalgic townhouses. On the tour, you will also get an insight into the gastronomy and cuisines of Caceres and the Extremadura region - with delightful paprika, cheese, Iberian ham, cherries, olive oil, lamb and superb wines. This evening, tuck into sumptuous seasonal cuisine at its 2 Michelin star restaurant,  a delightful presentation of Extremadura heritage by Chefs Jose Polo and Tono Perez. 

Overnight: Atrio Restaurante Hotel, Caceres

Meals: Breakfast & Michelin Dinner


A stunning day of lovely experiences begins with a pleasant drive south to the ancient UNESCO-listed Roman city of Merida, ancient capital of the Roman province of Lusitania. Discover why Merida was one of the greatest Roman civilizations outside of Rome with its impeccably well-preserved Roman monuments such as the Roman amphitheater and theater, its multiple-arched Roman bridge, the ruins of the Acueducto de los Milagros. We then continue south leaving the Extremadura region at the border with Andalusia where we make a visit to the rural settings of the village of Corteconcepcion where we visit a Jamon Iberico (Iberian ham) factory to gain an insight into the most-revered cured ham in all of Spain, learn about the habitat and freedom of the lives of Iberian pigs, raised on a diet of acorns that provides the delicious texture and taste of the ham. Visit the drying rooms and natural cellars where you will learn about the ageing process and elaborate details into Jamon Iberico production and finally, a tasting session where you will enjoy different varieties of ham accompanied with wines of the Huelva province in Andalusia. Thereafter, a short drive takes us to the town of Aracena, previously controlled by the Portuguese and the Knights Templar till the early 14th Century. We make a brief visit of the town followed by a panorama stop at the Castillo Fortaleza



Finally, our journey continues as we leave Spain entering into Portugal to the white-washed hilltop village of Monsaraz overlooking the beautiful Alqueva Lake near the border with Spain. Take a walk through this amazing and stunning town adorned with artisanal and wine shops - a true less-trodden gem of Portugal. We then retreat to the refined Sao Lourenco do Barrocal, a 200 year-old farm estate brought back to life as a modern day retreat surrounded by ancient oaks, olive groves and vineyards in the vastness of the Lower Alentejo plains. 

Overnight: Sao Lourenco do Barrocal, Monsaraz

Meals: Breakfast 


Today, we enjoy an excursion of the Alentejo countryside with a comforting drive north, passing many cork plantations and vineyards to the village of Vila Vicosa - decorated with many small palaces and manor houses with traditional marble and Manueline-styled architecture. Visit the 16th Century Ducal Palace of Vila Vicosa, built by the 4th Duke of Braganza in spectacular Mannerist style. We will also visit the 13th Century Castelo de Vila Vicosa - home to the earlier Dukes of Braganza before the construction of the Ducal Palace. Also worth visiting is the Agostinhos Church and Convent, the Santa Cruz, Capuchos, Esperanca and Chagas Convents


Later, we continue next to the UNESCO-listed fortified town of Elvas, famous for its stunning zig-zagging walls and fortifications where it was recaptured from the Moors in 1230. Due to its bordering location from Badajoz in Spain, it was constantly attacked before it fell to King Philip and the Spanish in 1580. Elvas' star-shaped walls were designed in the 16th Century by Flemish Jesuit engineer, Cosmander with two outlying forts to the north and south. Marvel at Elvas' quintessential sites such as the Igreja de Nossa Senhora da Consolacao, the Aqueduto da Amoreira, the English Cemetery and more. 

Overnight: Sao Lourenco do Barrocal, Monsaraz

Meals: Breakfast 


Enjoy a leisure morning where after breakfast, enjoy an exceptional guided horse riding excursion in the expansive farmscape of Sao Lourenco do Barrocal spanning over 780 hectares. Ride on the Lusitano horse, the oldest saddle horse in the world and unique to the Iberian Peninsula renowned for its noble characteristics and a status symbol since ancient times. Discover the ancient menhir, the vineyards, the cereal fields and vast pastures that is home to free-roaming cattles not mentioning unforgettable views of the Alqueva Lake and the village of Monsaraz in the distance. 


Later, we journey to the UNESCO-listed city of Evora on a walking tour around the medieval streets of this well-preserved city starting from the Praca do Giraldo lined with attractive townhouses with intricate wrought-iron balconies. Stop to admire the Roman Temple of Evora with its large Corinthian columns dating back to the reigns of Augustus. We then visit the Romanesque Cathedral of Evora, built in 1186 - one of the most sacred sites in Portugal. Head on next to visit the St Francis Church with the "Bones Chapel", completely decorated with human bones. We then stop by the local market for browse through, shopping for supplies where then we follow your guide to her home for a lesson on Alentejan cuisine, complete with wine and good company. 

Thereafter, continue our drive west where we make a visit to the Herdade do Menir wine estate from the Barao Rodrigues family of the Algarve to enjoy a tour of its winery and production and sampling of its exquisite wine. Finally, we will arrive at the L'AND Vineyards where we will check in and tonight, enjoy a sumptuous Michelin degustation dinner by Chef Miguel Laffan at its gastronomic restaurant. 

Overnight: L'AND Vineyards, Montemor o Novo

Meals: Breakfast, Lunch & Michelin Dinner


A delightful week in the Extremadura region in Spain and Alentejo region in Portugal comes to an end as you are transferred to Lisbon to continue your journey onwards or to Lisbon Intl Airport for your flight return. 



Meals: Breakfast


The Hospederia Valle del Jerte is located in the town of Jerte, near the natural pool of El Nogalon. The original building was used for leather tanning and later as an old mill. Now fully rehabilitated, it offers the comforts of a modern hotel with comfortable rooms and well-appointed amenities. 

Hospederia Valle del Jerte, Jerte Valley

Atrio Restaurante Hotel, Caceres

Located inside the walled town of Caceres with its extraordinary Almohad, Gothic, Renaissance and colonial buildings, Atrio boasts sublime architecture by Emilio Tunon Alvarez and Luis Moreno Mansilla, masters of modern design. In the heart of the old stone buildings of this medieval town, Chefs Jose Polo and Tono Perez prepare cuisine with unique, authentic flavours deserving of its 2 Michelin stars status. 

In the same family for over 200 years, Sao Lourenco do Barrocal is an ancient farming estate carefully brought back to life as a remarkable hotel of understated luxury, surrounded by ancient oaks, olive groves and vineyards. 

Sao Lourenco do Barrocal, Monsaraz

L'AND Vineyards is an exclusive retreat with only 22 suites integrating modern architecture into nature, providing an atmosphere of sober luxury, natural beauty and tranquility set in the heart of Alentejo, in an unique landscape. Enjoy a gastronomic journey in its Michelin star restaurant, rejuvenate in the Caudalie spa and sleep under the stars among the vineyards in one of the sky suites. 

L'AND Vineyards, Montemor o Novo


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