Andalucia, Castille, Extremadura and Portugal

Southern Iberia offers a fascinating journey best experienced during the milder months from mid-February to June or September to October.

We could begin near Madrid, where we visit the medieval city of Toledo, which  rises above the Tagus River, its strategic elevation having protected it through centuries of history. Once known as the “City of Three Cultures,” Toledo’s cathedral, churches, and winding streets beautifully reflect its harmonious blend of Christian, Muslim, and Jewish heritage.

Traveling westward brings you to Extremadura, a rugged region of plains and oak-studded grasslands that bred famous conquistadors like Cortés and Pizarro. Here, we can explore Cáceres with its multicultural architecture, and Trujillo, where an Arab castle stands alongside Renaissance palaces built by returning conquistadors. The region’s natural beauty unfolds in Monfragüe National Park’s diverse wildlife and traditional Dehesa farms, where prized Iberian ham is produced.

Crossing into Portugal’s Alentejo region, we can discover Marvão, a medieval fortress town dramatically perched atop a granite crag. This architectural gem, historically serving as a gateway between Portugal and its eastern neighbors, commands spectacular views of the surrounding countryside. Nearby, we are accompanied by archaeologists through fascinating Roman ruins and prehistoric sites. The historic town of Évora, once a favorite of Portuguese royalty, enchants visitors with its 13th-century square, historic university, intriguing Chapel of Bones, and the magnificent Roman Temple of Diana.

The journey could conclude in Andalucia, where diverse landscapes stretch from the Sierra Morena mountains to the Guadalquivir River. This region embodies centuries of cultural fusion, with Phoenician, Roman, Moorish, and Christian influences evident in every corner. Cities like Seville and Cordoba serve as living museums of this rich historical tapestry, their architecture and culture telling stories of civilizations past.

On the coast we can visit Doñana National Park, where Imperial eagles soar the skies. There are several very different picturesque small towns that we can stay in too, giving us the opportunity to go for hikes, observe the flora and fauna and get to know the inhabitants.

There is so much diversity and history in these areas that the choice of where to go is vast. With knowledge of your interests and preferred activities we would be happy to tailor a journey for you in this area.